Chicago Travelers Recommend

Chicago is famous for its architecture, especially its towering skyscrapers, and you can see it all on an architecture tour. Because building design evolved as the city grew, there’s plenty to learn about the storied history—here’s where to start.

Willis Tower — once the tallest building in the world

Formerly known as the Sears Tower, this downtown skyscraper stands 108 stories high, making it the second tallest building in the US. The 103rd-floor Skydeck offers spectacular views, and a step out onto the Ledge lets you look straight down to the street below. Make it a stop on a hop-on hop-off bus tour or book VIP access for breakfast, lunch, or dinner at the Skydeck. It’s also visible from most river and downtown walking tours.

John Hancock Center — offering the best views of Lake Michigan

The fourth-tallest building in the city, the John Hancock Center features a 94th-floor observatory and a 95th-floor restaurant, as well as the best views of Lake Michigan in the city. Don’t miss TILT—an enclosed glass platform that tilts guests out over Michigan Avenue from the 94th floor. Stop off at the center during a bus tour or see it from above on a helicopter tour of the city. 

Marina City — Chicago’s “corn cob towers”

Shaped like two corn cobs standing tall along the Chicago River, the Marina City towers were once the tallest residential buildings in the world. Today, they’re home to a mix of commercial and residential uses, including a hotel, bowling alley, several restaurants, and the House of Blues concert hall. View Marina City from an architecture boat cruise or a kayaking tour on the Chicago River.

Tribune Tower — neo-Gothic design on Michigan Avenue

Overlooking the Chicago River, the Tribune Tower features dozens of stones and bricks from historically significant sites all over the world, including fragments from the Berlin Wall, the Parthenon, the Great Wall of China, and Angkor Wat. View the tower on an architecture boat cruise or a walking tour of historic skyscrapers.

Wrigley Building — lighting up the Magnificent Mile

Across the street from Tribune Tower, the Wrigley Building was the first major office building north of the Chicago River. Check it out from the river below or by joining a walking tour of historic skyscrapers.

Chicago Cultural Center — stunning stained-glass domes

The Italian Renaissance-inspired interior of the Chicago Cultural Center (which formerly hosted the city’s central library) features gorgeous stained-glass domes, colorful mosaic floors, and walls made of green, white, and pink marble. Take a walking tour of the Loop focused on interior architecture or Tiffany glass.

Chicago makes up for its blustery winters with summer sunshine and high temperatures. Whether you choose to spend a day in the city’s parks, lounge on one of Lake Michigan’s beaches, or retreat to the air-conditioned calm of a museum when the afternoon sun feels particularly strong, here’s how to spend summer in the Windy City.

• Go for a cruise along the Chicago River, and admire the city’s famous skyscrapers from the water’s edge.
• Couple a sightseeing excursion to Millennium Park with a night of music at the Chicago Jazz Festival.
• Enjoy unparalleled fireworks views when you celebrate the Fourth of July aboard an all-night party yacht.
• Head to Grant Park, and come hungry: The Taste of Chicago Festival is one of the city’s most popular summer events.
• Retreat to the Art Institute of Chicago for a cultural immersion when the thermostat soars (or when summer thunderstorms roll in).
• Enjoy a celestial show at the Adler Planetarium —and go stargazing at its companion Doane Observatory.
• Sun yourself on one of Lake Michigan’s sandy beaches, such as North Avenue Beach or Oak Street Beach.
• Combine a fresh-air stroll with the opportunity to chow down during a food-themed, neighborhood walking tour.
• Commune with aquatic life during an excursion to the delightful Shedd Aquarium.
• Indulge in an urban oasis when you visit the blossoms at the Chicago Botanic Garden.

Whether spending a weekend in the Windy City or planning a midweek adventure, you have plenty of time to discover Chicago’s highlights in two days. From world-class museums and world-ranking skyscrapers to the city’s delectable dining scene, here’s how to make the most of your 2-day stay.

Day 1: The Loop and Beyond

Morning: Set right along the waterfront, Chicago’s Museum Campus (home to the Field Museum of Natural History, the Adler Planetarium, the Shedd Aquarium, and more) is the perfect place to immerse yourself in the Windy City’s cultural side.

Afternoon: The Loop, Chicago’s downtown business district, is home to a heavy concentration of landmarks. The neighborhood is ideal terrain for walking tours—explore on foot and stumble across highlights ranging from Millennium Park and the Willis Tower (formerly the Sears Tower) to public sculptures by Pablo Picasso and Alexander Calder.

Night: Head up to the top of the Willis Tower, where you can enjoy a multicourse meal while taking in views of Chicago lit up after dark. Alternatively, a dinner cruise along Lake Michigan combines gourmet dishes with splendid skyline views.

Day 2: Sand and Surf, Snacks and Sightseeing

Morning: On Chicago’s 26-mile (42-kilometer) shoreline, admire what might look to be the ocean—a stretch of Lake Michigan often called the “Third Coast.” When the sun’s out, follow Chicagoans to the lake’s sandy beaches, from North Avenue Beach to Oak Street Beach. Alternatively, enjoy waterside attractions of a different kind at Navy Pier.

Afternoon: Complete this day with a food tour of Chicago’s vibrant culinary culture. Seek out hot dogs and Italian beef sandwiches, and save extra room for deep-dish pizza. A number of renowned, decades-old pizza joints can be found right in the Loop, from Lou Malnati’s and Giordano’s to Gino’s East.

Night: When the sun is setting, embark on a helicopter tour and get rewarded with a unique, aerial perspective of the city. Spot Chicago’s most distinctive skyscrapers, discover its different neighborhoods from the air, and see the lights come on as evening descends.

Chicago may be 1,000 miles from the ocean, but the city is still best seen aboard a boat. From the Chicago River to nearby Lake Michigan, visitors are spoiled for choice when it comes to touring the city from the water. See below for your options.

Chicago River Cruises

Learn the history of Chicago’s skyscrapers on a Chicago River cruise, some of which focus specifically on the city’s towering architecture. See Sears Tower and the Wrigley Building while enjoying a casual architecture cruise, and hear how the flow of the river was reversed—a feat of modern engineering.

Sailing and Speedboat Rides on Lake Michigan

Lake Michigan is so big that its total area is larger than that of nine different US states, meaning you’ll feel like you’re cruising the open ocean on a sightseeing lake tour. Take a speedboat tour, dine on an evening buffet cruise, or enjoy a private sunset sail to see where the Chicago skyline rises up from the water and faces the deep blue horizon.

Combo Tours

If you can’t decide between the river and lake, choose a Chicago combo tour that includes both experiences. You’ll enjoy a casual cruise of the river and then race down Chicago’s coastline on a speedboat ride.

As a top US destination, Chicago welcomes more than 50 million visitors each year. That said, you can still enjoy a tranquil visit to the Windy City. From exploring by boat to discovering Chicago’s local restaurants and neighborhoods, here’s how to beat the crowds.

Explore the City by Boat

Instead of fighting the crowds of Magnificent Mile, take to the Chicago River or Lake Michigan, from which you can admire the Windy City’s skyscrapers and skyline without the crowds on an open-top boat tour; head out at sunset for the best views. 

Venture Beyond the Loop

The Loop—Chicago’s downtown business district—is home to top attractions such as Millennium Park, the Willis Tower, and the Art Institute, meaning that it’s reliably packed with visitors. Go beyond the Loop’s radius to see how locals live on a neighborhood tour, which tend to cover the heritage architecture of the Prairie District, street art in Pilsen, and the mansions of Wicker Park.

Discover Local Eateries

There’s more to Chicago’s food scene than deep-dish pizza. Enjoy shorter wait times and more diverse cuisine when you venture off-the-beaten-track. Food- and drink-themed neighborhood walks offer a first-hand introduction to many of the city’s less-trafficked culinary haunts, including the coffee shops of Logan Square, Chinatown, and the eateries of River North.

Visit Year-Round

As well as soaring temperatures, summer in Chicago brings peak crowds. For a quieter experience of the city, visit during the shoulder season. Alongside the crisp breezes and golden leaves of fall, you’ll encounter quieter museums and sidewalks. And if you don’t mind a winter-wonderland experience, the Windy City’s snowfall provides a magical backdrop to your exploration. 

Head Underground

One of Chicago’s most surprising attractions is the subterranean Pedway. Located beneath the Loop’s famed skyscrapers, the network lets you slip past crowds and discover a whole new side of the city. Book a guided tour to navigate the underground labyrinth with ease.

Take a Private Tour

Private and small-group tours allow you to the explore the city in a more intimate setting.  Soar over Chicago's iconic skyscrapers in a helicopter tour, or cruise along the lakefront on a private minibus tour customized for your group.

Chicago is blessed with world-class museums, extraordinary skyscrapers, beautiful beaches, and fabulous restaurants—and happily, it’s easy to take advantage of its highlights with the kids in tow. From river cruises and Segway adventures to pizza-themed food tours, here’s how to plan a family-friendly day out in the Windy City.

• Get a bird’s-eye perspective on the Windy City when you ascend to one of its skyscraper observation platforms: the Willis Tower’s Skydeck and 360 Chicago Observation Deck both offer unbelievable views.
• Exploring by boat is the perfect way to make sightseeing exciting for younger visitors. Wend your way along the Chicago River, or even head out on Lake Michigan.
• Chicago is a dream city for museum lovers—and cultural highlights like the Field Museum of Natural History, Adler Planetarium, and Art Institute of Chicago are fun to explore with the whole family.
• If you’ve got older kids in tow, enjoy a speedy way of discovering Chicago’s major landmarks when you zip around town by Segway or by bike.
• Given that Chicago’s culinary specialties include pizza and hot dogs, a wide-ranging tasting tour is sure to please kids and adults alike.

From skyscrapers to museums to vibrant neighborhoods to public parks, Chicago has something for everyone, and three days is more than enough time to explore its highlights. Travel by bus, bike, or on foot; linger in the bustling Loop; or head out of town on a day trip. Here’s how to plan your 3-day Windy City itinerary.

Day 1: Chicago’s Top Attractions

Explore Chicago’s most popular landmarks, many of which are concentrated in the Loop neighborhood, including Millenium Park and the Willis Tower Skydeck. Bus and bicycle tours of the area make it possible to see more in less time, while a hop-on hop-off bus itinerary offers a seamless overview of the city (plus the chance to disembark where and when you wish). Alternatively, combine your Loop adventures with a trip to another part of town. Catch an afternoon Cubs game at Wrigley Field on the North Side, or head to the South Side to explore Chinatown.

Day 2: Museums, Architecture, and Other Historical Highlights

Learn about Chicago’s past on an architecture tour—hop aboard a riverboat and cruise all three branches of the Chicago River, spotting highlights such as the Tribute Tower and the Merchandise Mart as you go, or head off on an intimate walking tour to view landmarks firsthand. Then, delve into Chicago’s esteemed museums, including the Field Museum of Natural History, Museum of Science and Industry, and the Art Institute of Chicago.

Day 3: Chicago Area Day Trip

Frank Lloyd Wright, a longtime Chicago resident and one of the 20th century’s most celebrated architects, designed a number of buildings in the Chicago area. Discover some of his best-known works on a day trip to the Frank Lloyd Wright Home and Studio in Oak Park, a village located just beyond Chicago’s western edge. Here you'll discover where the architect lived and worked for the first two decades of his career, and where he developed his signature Prairie School style. Oak Park’s other architectural gems include the Frank Lloyd Wright Historic District, Unity Temple, and the Arthur B. Heurtley House.

Poet Carl Sandburg famously described Chicago as “the City of the Big Shoulders,” and it’s true that this city has extraordinary breadth. Home to record-breaking skyscrapers and enviable lakefront views, world-class museums and dynamite restaurants, a buzzing downtown and historical neighborhoods packed with charm, Chicago is an utterly unique study in contrasts. Whether you wish to admire its architecture from the water’s edge, ascend to the top of one of the Western Hemisphere’s highest buildings, learn about the city’s sordid Prohibition dealings, or admire priceless canvases, this Midwestern powerhouse serves up a dazzling range of entertainment and sightseeing possibilities, no matter your interests. To help you narrow down the options, browse this collection of must-do activities—and get ready to make the most of your Windy City excursion.

You don't need a car to get around Chicago, thanks to a world-class public transit system, compact neighborhoods, and an easy-to-navigate grid layout in the downtown Loop area. Whether you’re keen to explore on foot, by train, or even via the city’s waterways, here are your options for making your way around the Windy City. 

Ride the “L” Train

Chicago claims the second-largest public transit network in the US, made up of buses and the city’s signature elevated rail lines, plus underground and street-level trains. You can buy single-ride tickets directly from bus drivers or via vending machines at rail stations. If you're planning to ride frequently, save with a 1- or 3-day unlimited pass. 

Hop On and Hop Off

If taking public transit seems daunting but you still want the flexibility to explore at your own pace, a hop-on-hop-off-bus tour is a user-friendly option. Multiple routes and dozens of stops can get you almost anywhere you want to go in Chicago, and you can learn about passing sights along the way through narration.

Catch a Water Taxi or Cruise

With many attractions along the Lake Michigan shoreline and the snaking Chicago River, Chicago can also be explored by water. Catch an affordable water taxi for a fun way to get between landmarks such as the Magnificent Mile, Chicago Riverwalk, and Chinatown. Architecture cruises are a popular way to learn about the city’s signature structures, while Lake Michigan cruises offer a new vantage point on the Chicago skyline, often with included dinner and drinks. 

Take a Walk

Chicago is defined by its neighborhoods, so soak up local character on a stroll through walkable “villages” such as Wrigleyville, Hyde Park, Andersonville, Wicker Park, and River North. Walking tours can help you discover ethnic eateries, architectural gems, gangster history, and more. 

Bike or Roll on a Segway

To cover more ground and fit in multiple neighborhoods, rent a bike or Segway and explore the city on two wheels. Guided tours can show you the best sightseeing routes, from the Lake Michigan shoreline to Loop landmarks or small-batch breweries.

Chicago’s skyline ranks among the most impressive on the planet, thanks to its magnificent skyscrapers representing numerous architectural styles. One of the best ways to experience the sights and sounds of the “Windy City” is while floating down the Chicago River. Here’s what you need to know to make a voyage yourself.

Highlights

• Take an architecture river cruise to learn why Chicago’s skyline is so impressive.

• Float past more than 40 notable buildings, including the John Hancock Building, Aon Center, Wrigley Building, and Willis Tower.

• See the illuminated waterfront, including the Buckingham Fountain, on a night cruise of the Chicago River and Lake Michigan.

• Combine a river cruise with a trolley city tour, minibus sightseeing tour, helicopter ride, or early access to the Willis Tower Skydeck.

• Chicago sightseeing cruises are offered aboard speedboats and double-decker riverboats.

Fall is a wonderful time to visit Chicago. Crisp breezes and golden leaves lend the Windy City a romantic, autumnal ambiance, but it’s still warm enough to enjoy open-air bus tours, cruises along Lake Michigan and the Chicago River, and engaging walking tours. Here’s what to do during your fall visit to the Windy City.

• Explore the city by boat, and catch glimpses of its most striking buildings, on an architecture river cruise.

• Admire stunning city views from the lofty heights of the 360 Chicago Observation Deck.

• Discover a true Chicago icon when you visit the world-famous Willis Tower.

• Visit Al Capone’s former haunts (and learn about the city’s sordid past) on an alternative history tour.

• See where the Cubs made World Series history on a walking tour of Wrigleyville.

• Sip acclaimed Illinois wines aboard a Lake Michigan boat tour.

• Use a Chicago Explorer Pass to craft your own sightseeing itinerary (and visit the city’s top museums and attractions).

• Make the most of your time in the Windy City on a h op-on hop-off bus tour.

• Get to know Chicago’s spooky side during a Halloween-themed bike tour.

• Step back in time to the Roaring Twenties at a speakeasy-themed dinner show.

If you only have one day to see Chicago, don’t worry. That’s more than enough time to get acquainted with the Windy City’s ineffable style, lofty skyline, and numerous cultural attractions. From architecture cruises along the Chicago River to skyscraper observation decks, here are some suggestions for the perfect sightseeing day in Chicago.

Morning: Chicago’s Green Spaces

Start your day by looking beyond Chicago’s urban jungle of skyscrapers. The city has plenty of vibrant green spaces to be seen by bike or Segway tour. Millennium Park, within the larger Grant Park, has become one of the city’s most popular attractions since it opened in 2004. Stretching across 25 acres (10 hectares), the park’s highlights range from the verdant Lurie Garden to the playful Crown Fountain and Anish Kapoor’s reflective Cloud Gate sculpture, commonly known as “The Bean.”

Afternoon: Architectural Sights

From the soaring spires of the Willis Tower and the John Hancock Center to the famous Marina City buildings and the landmarks along Magnificent Mile, Chicago is an architecture lover’s city. One of the best ways to take in the sights is on a cruise along the Chicago River. Find a seat on the deck, and crane your neck upward as your tour guide shares stories about how the city’s skyline came to be. Alternatively, a walking tour lets you get intimate with the landmarks, head into building lobbies to admire interior architecture, and delve into their history.

Evening: Aerial Views

Chicago is a skyscraper city—until One World Trade Center debuted in New York City in 2013, the Willis Tower (formerly known as Sears Tower) was the tallest building in the Western Hemisphere. In addition to being a Chicago landmark, the building offers some of the best views of the cityscape and Lake Michigan beyond. Book Skydeck admission tickets to take an elevator 100 floors above the city and admire a panoramic perspective of Chicago after dark. If that isn’t sufficiently lofty, evening helicopter tours also provide an excellent aerial vantage point for night sightseeing.

Chicago boasts a diverse arts-and-entertainment scene that ranges from museums and theaters to comedy clubs and cutting-edge architecture. Here’s how to expand your cultural horizons in the Windy City. 

Head to the Museums

Chicago has a surfeit of world-class museums, making it the ideal stop for culture vultures. Explore the Art Institute, home to works by Seurat and Picasso; head to the Field Museum to scope out dinosaur fossils and learn about natural history; and then continue to the Adler Planetarium for a celestial show. Book your admission tickets in advance to save time on the day. 

Discover Architectural Highlights

From skyscrapers and art deco masterpieces to heritage landmarks such as the Rookery Building and Marina City, Chicago is celebrated for its architecture. Admire top Chicago structures during a narrated river tour by open-top boat; go for a historian-led walking tour to see famous buildings up close; or book a day trip to discover Frank Lloyd Wright’s most significant Chicago-area works.

Spend the Night at the Theater

Chicago rivals New York for its theater scene and range of blockbuster shows. By day, see a different side of the Chicago Theater or the Auditorium Theatre on a behind-the-scenes tour. Then, when the sun goes down, book tickets to a musical at the Lyric Opera.

Go on a Speakeasy Time Warp

Prohibition ranks among the most infamous chapters in Chicago’s history. A variety of history tours bring the 1920s- and ’30s-era to life: take a gangster-themed tour to learn about Al Capone’s notorious crimes or follow a historian to the sites of former underground cocktail bars. 

Hit the Comedy Club Circuit

Many of comedy’s biggest stars—from Tina Fey and Steve Carrell to John Belushi and Stephen Colbert—spent time honing their craft in Chicago. No night out in the Windy City is complete without a tour of its comedy clubs; book tickets to an improv show at The Second City or go on comedy tour to visit several venues in one go. 

The Prohibition Era was a colorful time in the "The Windy City" with mobs and gangs running rampant—everyone from Al Capone to John Dillinger—and plenty of speakeasies where the liquor flowed. Here are the options to learn more about the era on a gangster tour of the city.

Mafia and Prohibition History in Chicago

See the spots once ruled by liquor, jazz, and the mafia on a Prohibition history tour. Visit relevant sites such as the Holy Name Cathedral, Biograph Theatre, Clark Street Bridge, and the site of the St. Valentine’s Day Massacre in 1929. Private tours include a Chicago nightlife option and a Chicago blues and Jazz Age history option.

Speakeasy & Cocktail Tours

Another way to experience the city’s Prohibition era is to visit the pubs and bars that defied the 10-year alcohol ban. Speakeasy bars across the Old Town district, Wicker Park, and the Chicago Loop come to life on cocktail-themed tours.

Crime and Gangsters Tours

Learn about the Chicago crime of the past and take a trip back in time to the 1920s, ‘30s, and ‘40s on a crime and gangster tour. Hear stories about the iconic murders and crime scenes from this infamous time in the city's history. Explore Chicago's North Side, Lincoln Park, Gold Coast, Magnificent Mile, and other neighborhoods that are part of the city's gangster past.

Spring in Chicago brings a gentle thawing of the winter snows, newly balmy temperatures, and more excuses than ever to go exploring. From bike tours to hop-on hop-off bus journeys, Lake Michigan cruises to foodie-frequented walking tours, here’s what to do during your springtime visit to the Windy City.

• Admire Chicago’s ineffable skyline from the water’s edge during a Lake Michigan sightseeing cruise.

• Take in stunning city views with a glass of prosecco in hand atop the 360 Chicago Observation Deck.

• Zip through Chicago’s neighborhoods and enjoy the fresh spring breeze on a Windy City bike tour.

• Pair local nibbles with a springtime stroll during a culinary walking tour of the Loop.

• Dine and dance with abandon while taking a sunset cruise.

• Score a seat on the top deck during a hop-on hop-off Chicago bus tour.

• Plan your own cultural itinerary and explore Chicago’s many museums.

• Fuel up with an indulgent visit to a Chicago-style pizzeria(or several).

• See the neon-lit cityscape during a nighttime helicopter tour.

• Trade the urban bustle for a day in southwest Michigan’s burgeoning wine region.

Food is a big deal in Chicago, but if there’s one dish most associated with the “Windy City,” it’s Chicago-style pizza. This gooey, cheesy, deep-dish pizza, characterized by its thick cornmeal crust, was invented by Pizzeria Uno in 1943. Here’s how to try it.

Dining Experiences

Cross two items off your Chicago to-do list with a sky-high meal at Skydeck, the observation deck at the top of the Willis Tower. Tuck into a Chicago-style pizza while taking in the evening views of the city below. While deep-dish pizza is the city’s most popular style, the pizza scene is more diverse than that. Explore the food culture on a pizza-centric bus tour, with stops to sample slices ranging from deep-dish to thin crust.

Neighborhood Food Walking Tours

Each Chicago neighborhood has its own distinct personality (and usually a few pizza joints). One of the best ways to experience the food scene is to hit the pavement on a culinary walking tour in neighborhoods such as Old Town, Gold Coast, River North, Wicker Park, Bucktown, Naperville, Lincoln Square, or West Loop. Dive deep into the city’s Italian heritage with samples of pizza and Italian beef on an Italian food tour, or take your stomach on a walking tour of Chicago’s other famous foods, such as Chicago dogs, Italian beef sandwiches, popcorn, and chocolate.

While you might start your exploration of Chicago’s food scene with an iconic deep-dish pizza or a Chicago-style hot dog, that's just the beginning. The city has been influenced by Polish, Italian, and Greek cultures, and the result is an array of traditional and fusion eateries. Here are some of the Windy City’s must-try dishes. 

Pizza

Chicago-style deep-dish pizza is the city’s most prized culinary treasure. Layered with mounds of cheese, meat, vegetables, and tomato sauce, the inches-thick pie is baked in a pan until its buttery crust reaches a satisfying level of crunch. Due to their heft, slices often have to be eaten with knife and fork. 

Chicago-style Hot Dog

Chicago does hot dogs like nowhere else. The city’s signature dog can be found on street corners and in restaurants all across town. To qualify as a traditional Chicago dog, an all-beef frankfurter must be served on a poppy seed bun topped with yellow mustard, chopped onions, bright green relish, hot peppers, tomato slices, a dill pickle spear, and a dash of celery salt—with absolutely no ketchup. 

Italian Beef Sandwiches

In one telling of its origins, the Italian beef is a result of thrifty ingenuity. Scala's Original Beef and Sausage Company claims it started thinly slicing beef and loading it onto gravy-soaked bread to feed more people at weddings around 1925. The idea caught on, and today the Italian beef sandwich, loaded with peppers, served on French bread, and dipped in au jus, is one of Chicago’s most sought-after eats. 

Polish Sausage

The Maxwell Street hot dog stand has been serving the same Polish sausage recipe since 1939. Loaded with sweet grilled onions and yellow mustard, the Maxwell Street Polish is a staple at hot dog stands and eateries throughout the city. 

Rainbow Cones

The Original Rainbow Cone is one of the oldest ice cream shops in Chicago, and its signature cone is piled high with a rainbow of flavors. Each cone is layered with a curious combination of chocolate, strawberry, Palmer House (a flavor made of vanilla with cherries and walnuts), pistachio, and orange sherbert. 

Old Fashioned Donuts and Cinnamon Rolls

Chicagoans have always been serious about their fried dough. Quality doughnut shops from old-fashioned bakeries to gourmet pastry shops are found in nearly every neighborhood around town. The cinnamon rolls at Ann Sather’s Swedish diner are another Chicago food favorite.

The Windy City may be famous for its snowfall, but don’t let that dissuade you from visiting. Chicago transforms into a winter wonderland during the cold months. Explore its holiday light displays, visit its festive markets, and enjoy cozy stints in the city’s museums and speakeasies. Here’s how to plan the perfect winter getaway to Chicago.

• Pair a visit to the sky-high Willis Tower Skydeck with a Chicago-style pizza meal.

• Visit some of the Windy City’s coziest and most atmospheric speakeasies during a Prohibition-themed tour.

• When the weather is frightful, enjoy an indoor day at the Field Museum of Natural History, Art Institute of Chicago, or Adler Planetarium.

• Visit Christmas markets, skating rinks, and other seasonal attractions during a holiday stroll and food tour.

• View the Windy City from the sky during a ride in a helicopter that’s been decorated with holiday lights.

• Discover the city’s holiday light displays by trolley, private vehicle, or Segway.

• Plan a New Year’s Eve to remember by booking a luxury dinner cruise on Lake Michigan.

Chicago’s friendly neighborhood feel and proud industrial roots make it a welcoming city for travelers on a budget. With abundant museums, casual eateries, and public parks connected by an efficient public transit system, it's easy to experience the best of Chicago cuisine and culture without breaking the bank. Here's how.

Explore More with a Sightseeing Pass

Save big on Chicago's top attractions with a sightseeing pass such as the Go Chicago Explorer Pass or Chicago CityPass. Customize a pass with your choice of attractions such as the Shedd Aquarium, Skydeck Chicago, Museum of Science and Industry, and Adler Planetarium, and enjoy discounts of up to 40 percent on admission. 

Get Around on a Hop-On-Hop-Off-Bus Tour

Avoid the expense of car rental by utilizing Chicago's excellent public transit network or booking a hop-on-hop-off-bus tour. These affordable and user-friendly tours combine narrated sightseeing with the flexibility to design your own itinerary, with stops at dozens of Chicago's must-see landmarks. Bonus: The buses are heated during Chicago’s famously frigid winters.

Visit Top Chicago Museums

Chicago's world-class museums are a great way to get cultured on the cheap. From creative collections at the Art Institute of Chicago to science-focused exhibits at the Field Museum and Adler Planetarium, there's something for everyone. Check local event listings for museum free days to save even more. 

Find Budget-Friendly Bites

Happily for budget travelers, most of Chicago's signature dishes are heavy on taste but light on the wallet. Look for abundant street fare and casual eats such as deep-dish pizza, loaded Chicago hotdogs, and popcorn. Chicago food tours can show you how to find the most authentic snacks and bars in the city, often for less than the price of a single fine-dining meal.

Chicago is a city with style and verve, and its beautiful parks, picturesque waterways, and vertiginous heights all make the perfect backdrop to a romantic excursion. From 2-passenger helicopter flights to Lake Michigan cruises and after-dark speakeasy visits, here’s how to enjoy a special trip to Chicago with your significant other.

Cruise Lake Michigan at Sunset

Lake Michigan is almost oceanic in scope, and a night out on the water is a classic Chicago experience. Book an early evening tour to watch the sun descend over the iconic Chicago skyline, and enjoy a romantic moment out on the deck. Alternatively, a dinner cruise—complete with gourmet dishes and flutes of sparkling wine—is the perfect way to toast a special occasion.

Enjoy a Couple’s Photo Shoot in Millennium Park

Visit one of the Windy City’s most in-demand sightseeing destinations—and enjoy a special way to record your memories for posterity—when you book a couple’s photo shoot. Explore the greenery and public artworks of Millennium Park, admire the perspective on the Loop’s gleaming skyscrapers, and see the famous Cloud Gate sculpture by Anish Kapoor—better known as “The Bean.” Your very own photographer will be present to show you the sights and capture your romantic moments.

Sip Cocktails in the City’s Speakeasies

During its Prohibition-era heyday, Chicago was filled with speakeasies (not to mention infamous gangsters the likes of Al Capone). Today, that legacy lives on in the city’s plethora of top-notch cocktail haunts (which, today, are thankfully free of bathtub gin). Book a speakeasy tour for a dose of history and to discover a number of cozy, candlelit drinking dens with your significant other.

Book a Private Helicopter Tour

Few views of Chicago can compare with the ones afforded by a helicopter—and taking to the air on a freewheeling journey above the skyscrapers is one of the city’s most popular romantic experiences. Book a private flight for a particularly intimate experience, and enjoy an indulgent accompaniment in the form of Champagne and chocolates.

With museums covering subjects from science and natural history to architecture and modern art, Chicago is a playground for culture lovers. It would take months to visit the city’s 60 museums, so here are a few that should be at the top of your list.

Field Museum of Natural History

Chicago’s Field Museum of Natural History is one of the largest of its kind. You’ll journey through four billion years of the Earth’s history and see dinosaurs and ancient Aztec artifacts, and one of the world’s largest collections of gems and diamonds.

Art Institute of Chicago

The Art Institute of Chicago is one of the largest art museums in America and home masterpieces by Van Gogh, Renoir, Picasso, and more. The museum has an extensive collection of modern art including Grant Wood’s famous American Gothic.

Museum of Science and Industry

Chicago’s Museum of Science and Industry boasts a collection that encompasses a full-sized World War II German submarine; the first ever diesel-powered railroad train; and a replica of a working coal mine. The museum’s exhibits are diverse; you’ll find displays on everything from weather and electricity to airplanes and space stations, alongside a collection of real human specimens.

Chicago History Museum

Many of Chicago’s early historical documents were destroyed in the Great Chicago Fire of 1871, but those that survived can be found in the Chicago History Museum. The museum highlights the city’s past and present and showcases exhibits on Abraham Lincoln, the Chicago Blues, and even the Chicago Hot Dog.

Adler Planetarium

Journey through space and time during an immersive theatre experience in America’s first planetarium. In addition to space adventure shows and and star programs, the Adler also features hands-on astronomy exhibits where you can learn about the first moon landing, black holes, comets, and more.

Chicago Architecture Center

Discover the stories of Chicago’s architectural treasures at one of the city’s newest museums, the Chicago Architecture Center. You’ll find models of the city’s most impressive skyscrapers and an interactive films that explains how Chicago was rebuilt after the Great Chicago Fire.

Don't let the rain stop you from making the most of your time in Chicago—many of the Windy City's must-see sights are actually indoors, so there's no need to hole up in your hotel room. Here are a few ideas for rainy days in Chicago.

• See the gray skies from a new point of view on the glass-enclosed balcony at the Willis Tower's 103rd-floor Skydeck.
• Bring the kids (or your inner child) to the LEGOLAND Discovery Center.
• Stay out of the rain at one of the city's myriad museums, such as the Field Museum of Natural History, the John G Shedd Aquarium, or the Chicago Children's Museum.
• The famous Chicago Pedway, a network of underground tunnels and overhead bridges, runs throughout the downtown area, making it easy for both locals and visitors to avoid the elements and get around without ever stepping foot outside.
• See the city's sights and architecture at street level without getting wet on a hop on, hop off bus tour or a guided sightseeing experience by bus.
• Come nightfall, catch some live music at the House of Blues or a show at the Briar Street Theater to stay dry.

The Windy City is a destination of icons—famous foods, sports teams, architectural wonders, and historic blues bars. It’s a multifaceted metropolis with a lot going on, both on and off the tourist path. Here are a few ways to experience Chicago like a local.

Highlights

• Hit the waters of Lake Michigan during a private sailing excursion along Chicago’s stunning lakefront.

• Explore Chicago’s top-notch craft beer scene with a ride on the Brewery Barrel Bus.

• Grab a paddle and go kayaking at twilight to watch the fireworks over Navy Pier.

• Skip the line at one of Chicago’s top museums, including the Art Institute of Chicago, Alder Planetarium, Museum of Science and Industry, or Field Museum.

• Indulge in a favorite Chicago pastime—retail therapy—with a shop and spa tour along the Magnificent Mile.

• Rent a bike and hit the pavement for a self-guided tour of Chicago’s vibrant and diverse neighborhoods.

From the art installations of Millennium Park to the lakeside scenery of Lincoln Park, Chicago’s parks are among the city’s top attractions. Here are a few Chicago parks and gardens you won’t want to miss.

Millennium Park

Chicago’s Millennium Park is one of the city’s top attractions, so most city tours stop here. Located in downtown Chicago, the park’s centerpiece is a giant reflective sculpture called Cloud Gate. The park hosts a yearly programme of outdoor concerts, film screenings, and special events.

Lincoln Park

Dedicated to Abraham Lincoln, Lincoln Park stretches for 6.5 miles (10.5 kilometers) along Lake Michigan and is the city’s largest park. Visit the park on a bike tour of Chicago’s lakefront and discover top city attractions such as Lincoln Park Zoo and Lincoln Park Conservatory.

Grant Park

Nicknamed Chicago’s front yard, Grant Park separates downtown Chicago from Lake Michigan. The park is home to the Art Institute of Chicago and the Field Museum of Natural History, as well as multiple walking paths, seasonal concerts and events, and Chicago’s most-photographed fountain—the Clarence Buckingham Memorial Fountain. Most Chicago sightseeing, biking, and hop-on hop-off bus tours stop at Grant Park.

Jackson Park

Jackson Park was the venue of the 1893 Chicago World's Fair, which is memorialized with a replica of the event’s sculpture, The Republic. Today, the 600-acre (243-hectare) park boasts a golf course, tennis courts, and playground, as well as the Garden of the Phoenix, a Japanese-styled garden.

Northerly Island Park

For fantastic views of the Chicago skyline, head to the Northerly Island Park. This 91-acre (37-hectare) man-made peninsula, which juts into Lake Michigan, is a nature preserve home to some of the best fishing spots in Chicago. The park’s Huntington Bank Pavilion hosts music concerts during the summer months.