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Things to do in
Chicago

The Mecca of the Midwest is famous for its architectural beauty, vibrant culture, and colorful past.

Our most recommended things to do in Chicago

Chicago River: 1.5-Hour Guided Architecture Cruise

1. Chicago River: 1.5-Hour Guided Architecture Cruise

Experience more of Chicago by boat than on any other architectural cruise. See architectural highlights and enjoy an open-air deck or climate-controlled interior as you travel the main River and its north and south branches. View all of Chicago's architectural highlights during this comprehensive sightseeing tour. Be entertained by the expert and friendly tour guides as they explain the 130 year-long history behind the skyline, while bartenders and staff keep you comfortable with refreshments.  Choose between the fresh air of the open-air decks or enjoy the comfort of the climate-controlled interiors during your cruise. The tour starts at the Michigan Avenue (DuSable) bridge and goes up the main branch of the Chicago River past Wolf Point. It then cruises along the north and south branches of the river, before heading back past the Chicago Riverwalk towards Lake Michigan. On the way, learn about ornate, historic early skyscrapers like the Wrigley Building and the Tribune Tower, the imposing art deco Merchandise Mart, mid-century skyscrapers like the Mies Van der Rohe AMA Building. Don't miss the circular Marina City Towers, the majestic Willis Tower (formerly the Sears Tower and the tallest building in Chicago) the soaring AON Center, and more modernist structures like Aqua, Trump Tower, Nuveen, and the new Vista Tower. During your cruise, have the opportunity to enjoy a full-service cash bar featuring authentic Chicago products, including local beer and spirits, and Garrett’s Popcorn. Don’t forget to take a selfie at the Grand Staircase at the front of the boat or pose for photos at the picturesque stern or bow of this classic vessel.

Chicago: 360 Chicago Observation Deck Skip-the-Line Ticket

2. Chicago: 360 Chicago Observation Deck Skip-the-Line Ticket

Marvel at the views from 1,000 feet over Chicago’s legendary Michigan Avenue with this ticket to the 360 CHICAGO observation deck on the 94th floor of the John Hancock Center. Save time with skip-the-line access to this popular attraction. Head up to the 360 CHICAGO observation deck to take in breathtaking views of Chicago’s lakefront and view the city skyline from above. Take a peek at 4 neighboring states from this height. Feel the thrill of a 40-second ride in one of North America's fastest elevators to the observation deck to experience what 'Travel & Leisure Magazine' voted one of the best views in America. Enjoy an interactive exhibit on the Ground Floor that highlights Chicago’s rich history and showcases 9 of the city’s culturally unique neighborhoods. On the 94th floor, explore the history and architecture of the magnificent city stretched out before you. To enhance your experience, download the Magnicity App for a guided tour right from your smartphone. The App includes an interactive viewfinder, unique facts, stories and recommendations. Enjoy a thrilling photo opportunity at CloudWalk, a breathtaking 3D mural with the optical illusion of walking in the clouds. Relax and take in the view at the 94th floor’s Cloud Bar which serves up iconic Chicago snacks, neighborhood-inspired Cocktails, and a local brew, Moody Tongue, on tap. By purchasing this timed ticket, you get to skip the ticket desk and present your barcoded voucher to security to be scanned - you may have to wait in a short line at security, then head directly into the Ground Floor Exhibits, and then on to the Elevator Line.

Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

3. Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Experience the views from the Centennial Wheel at the Historic Navy Pier in Chicago with this attraction ticket. Be suspended over Lake Michigan at the mouth of the Chicago River. Marvel at the Chicago skyline and gaze out over the sparkling waters of Lake Michigan. Choose between two options: With the Regular Barcoded ticket, skip the ticket line and enter the line to board the wheel. The Fastpass Express ticket allows you to skip both lines, and gives you VIP access. Both tickets allow you to visit within 7 days of your scheduled ticket date. Enjoy the Centennial Wheel, which was built in 2016 to celebrate the 100th anniversary of the Navy Pier opening. Featuring 42 gondolas, each holding 8 people, it operates year-round. They also feature LED lighting, padded seats, TV screens, and speakers, as well as panoramic windows on all 4 sides. A ride on the wheel gives you plenty of time to enjoy these panoramic views of Chicago as they unfold around you, and allows you to visit the top three times. Relax and take in the view, or get your camera out to snap pictures of the ever-changing Chicago landscape.

Chicago: 45-Minute Family-Friendly Architecture River Cruise

4. Chicago: 45-Minute Family-Friendly Architecture River Cruise

Admire Chicago’s impressive architecture from a unique perspective aboard a cruise sailing down the Chicago River, which features an indoor and outdoor deck, along with live commentary tailored to entertain the whole family. Treat yourself to a full-service cash bar at your own expense. Experience the best of the Chicago River from Lakeshore Drive to the Willis Tower, navigating along the South branch of the river, before heading back past the Chicago Riverwalk towards Lake Shore Drive and Lake Michigan. Be entertained by the fun and experienced tour guides as they explain the history behind Chicago’s buildings along the river and the exceptional architects who created this ever-changing skyline. Enjoy the most relaxing way to sightsee in Chicago, exploring the city free of traffic, noise, and congestion. Make sure to visit the full-service cash bar featuring authentic Chicago products, including local beer and spirits. Explore the open-air decks that allow you to feel the cooling river breeze and see the city from many vantage points that provide perfect photo opportunities.

Chicago: Willis Tower Skydeck and The Ledge Ticket

5. Chicago: Willis Tower Skydeck and The Ledge Ticket

Enjoy an unrivaled view over the city of Chicago on a trip up the city's Willis Tower. This famous building, once known as the Sears Tower, is not only home to a Skydeck on the 103rd floor, but it also features The Ledge, a series of 4 glass-paneled boxes that extend out from the building's facade to give visitors a view straight down. As you wind through the ground levels of the Willis Tower, you will be surrounded by museum-quality exhibits highlighting the iconic tower. Learn about Chicago's rich history and culture through these informative visuals. Watch a video presentation, "Reaching for the Sky," where you will be briefed on the history of the building and of architecture in Chicago. Then step into your elevator and you will be amazed at how quickly it ascends. As you travel, your multimedia-equipped elevator will inform you about your vertical progress. Upon reaching the 103rd floor, step out onto the Skydeck, which offers views spanning over 50 miles and across 4 states. Then summon your courage to step out onto The Ledge, a glass balcony that hangs over the edge, for vertigo-inducing views 1,353 feet (about 412 meters) straight down to the city below! Download the Skydeck Mobile App for a free viewfinder which points out many of Chicago’s notable landmarks. Learn more about sights like Navy Pier, Wrigley Field, Grant Park, Art Institute of Chicago, Shedd Aquarium, and Field Museum of Natural History.

Chicago: 1.5-Hour Lake and River Architecture Cruise

6. Chicago: 1.5-Hour Lake and River Architecture Cruise

Experience an architecture cruise along the Chicago River and Lake Michigan, a family tradition since 1935. Admire Chicago’s historic and ever-changing skyline with a local expert guide as you cruise through the city. Choose between the open-air decks or the comfort of the climate-controlled interiors during the cruise. Start the cruise at Michigan Avenue (DuSable) bridge and go up the main branch of the Chicago River to Wolf Point before heading back past the Chicago Riverwalk towards Lake Michigan. Learn about historic skyscrapers like the Wrigley Building and the Tribune Tower, the deco Merchandise Mart, mid-century skyscrapers like the Mies Van der Rohe AMA Building, the circular Marina City Towers, the AON Center, and modernist structures like Aqua, Trump Tower, Nuveen, and the Vista Tower. After passing through the Chicago Lock and cruising past Navy Pier, admire the Chicago skyline from Lake Michigan, one of the largest bodies of fresh water in the world. Here you can also see the twin super-skyscrapers, the famous Willis (formerly Sears) Tower, and the John Hancock Building. See the majesty of Grant Park with its famous Buckingham Fountain, and iconic Chicago venues such as Soldier’s Field, Adler Planetarium, and the Shedd Aquarium. Enjoy several vantage points for memorable pictures throughout, and finally arrive back at Du Sable Bridge on Michigan Avenue.

Chicago: Architecture River Cruise Skip-the-Ticket Line

7. Chicago: Architecture River Cruise Skip-the-Ticket Line

Skip the lines at the ticket office and climb aboard a state-of-the-art cruise for a 60- or 75-minute cruise of all 3 branches of the Chicago River, and marvel at the architecture that has made the city so legendary. Get an insight into the buildings and engineering of a city that gave birth to the skyscraper and is the spiritual home of modern American architecture. Your expert guide will lead you down the Chicago River to uncover hidden gems, as well the city’s most renowned landmarks, such as the John Hancock building, Trump Tower, Marina City, Willis Tower, and more. Relax with a glass of something cold from the cash bar, as you cruise the Windy City’s waterway, and learn its status as a modern metropolis and one of the world’s most beautiful cities. End your tour in the same place where you boarded the boat.

Chicago: Gangsters and Ghosts Guided Walking Tour

8. Chicago: Gangsters and Ghosts Guided Walking Tour

Discover a different side of Chicago on a family-friendly guided tour and hear the tales of the ghosts, and gangsters, that haunt the city. Explore the Chicago South Loop district with your historian guide, uncovering the many mysteries hidden behind every turn. Meet your guide in the heart of the Chicago South Loop, known as a notorious vice district during the 1920s and 30s. Stroll through his now upmarket area of the city which was once home to underground speakeasies, secret tunnels, and bootleggers. Hear the true stories of Chicago's bloody past and the gangsters who caused havoc in the city. See the places notorious figures such as Al Capone used to party, make deals, and carry out "business". You will also enjoy a short rest stop at a famous former gangster hangout. Discover the legends of the ghosts that are said to lure along the Chicago Riverwalk and the aptly named Death Alley. Stop at haunted locations including Palmer House, and the Chicago Theatre, before finishing with a visit to the Congress Hotel, one of the most haunted places in Illinois.

Chicago: 1.5-Hour Romantic Sunset Cruise

9. Chicago: 1.5-Hour Romantic Sunset Cruise

Relax as you glide over the Chicago River and into Lake Michigan on this cruise. Enjoy the glow of the sunset on Chicago's sparkling skyline. Have the option to purchase delectable drinks and snacks at the onboard bar as you sail. Start your sunset cruise on the Chicago River at Michigan Avenue. Make your way along the main branch of the river towards Lake Michigan before entering the Chicago Locks, a modern engineering marvel, that will transfer the vessel onto the great Lake Michigan. The vessel will cruise along Lake Michigan as the sun sets behind the wonderful skyline offering several amazing views. Your local tour guide will give a very brief commentary along the Chicago River and entrance to Lake Michigan, but most of the 1.5-hour cruise is spent without narration, leaving you to watch the sun put on a beautiful display with the City skyline. Admire the many angles of the Chicago skyline from Lake Michigan, one of the largest bodies of fresh water in the world. Capture magical views of Chicago's twin super-skyscrapers, the famous Willis (formerly Sears) Tower and the John Hancock Building. You'll also get to admire the majesty of Grant Park with its famous Buckingham Fountain, and iconic Chicago venues such as Soldier’s Field, Adler Planetarium, and the Shedd Aquarium. During your cruise, treat yourself at the full-service cash bar featuring authentic Chicago products. Try local beer and spirits and Garrett’s Popcorn. Choose between the fresh air of the open-air decks or enjoy the comfort of the climate-controlled interiors during your cruise. Don’t forget to take a selfie at the Grand Staircase at the front of the boat or pose for photos at the picturesque stern or bow of this classic vessel.

Chicago: Hop-on Hop-off Sightseeing Tour by Open-top Bus

10. Chicago: Hop-on Hop-off Sightseeing Tour by Open-top Bus

Experience the best of Chicago at your own pace from the unique vantage point of a Big Bus tour. Board our open-top, double-decker bus as you take a relaxing ride through the city's most iconic landmarks, from the Magnificent Mile to Millennium Park. Hop on and off at our convenient stops throughout the city to discover Chicago's vibrant neighborhoods and world-famous attractions including 360 CHICAGO, Willis Tower, the Chicago Riverwalk, Museum Campus, The Bean, and more. Spend your day shopping on Magnificent Mile, riding the Ferris Wheel at Navy Pier, or sampling authentic Chicago Deep Dish Pizza. With our flexible and convenient tour, create your own itinerary and explore the city at your own pace. Track bus arrivals in real time with our free downloadable app so you always know when the next bus is coming. Marvel at the stunning skyline as you enjoy professional digital commentary in multiple languages, with earbuds provided. Hear expert insight into Chicago's rich history and culture, as well as tips on the best places to eat, drink, and shop. With comfortable seating and panoramic views, our Hop-On Hop-Off Sightseeing Tour is the perfect way to see the city. Hop off the tour as many times as you like within the validity period of your ticket and simply hop on again when you're ready to keep exploring.

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Top sights in Chicago

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Frequently asked questions about Chicago

What top attractions are a must-see in Chicago?

Insider tips: Explore Chicago like a local

Megan & Aram is a travel blog that focuses mostly on travel in the Nordics and Eastern Europe with the occasional trip beyond those regions. We love coffee, promoting small businesses, and sports.

What should I do on my first trip to Chicago?

Chicago is the third largest city in the United States and there is an endless number of things to do for every type of visitor. If you're visiting Chicago for the first time, start your day at Milennium Park and The Bean - which has, over time, become a symbol of the city. If you're lucky, you may even get to experience a free concert or gathering there during your trip! Don't leave the area before heading out onto Navy Pier for a few photos.

You can't visit Chicago as a first-timer without heading to The Skydeck at Willis Tower. What was previously known as the Sears Tower is now the Willis Tower and is one of the tallest buildings in the Americas! You can step out onto the glass-bottom Skydeck for an epic view of the city and since you'll be 1,353 into the air, you will be able to see everything!

Some museums worth checking out are the Art Institute of Chicago and the Museum of Science and Industry.

If you need an escape from the city, there are plenty of day trips from Chicago that will give you the downtime you need.

What are some hidden gems to see in Chicago?

Chicago is teeming with hidden gems and one of the best places to visit to experience one of the city's most underrated places is the 606 - a park and trail system that has been transformed from its days as an old railroad line. The 2.7-mile trail goes through the city connecting various neighborhoods. Another hidden gem is Promontory Point which is located in Burnham Park. This man-made peninsula offers some of the top views in the city - and you can see the skyline and Lake Michigan while sitting in a relaxing spot. Chicago also has some of the coolest neighborhoods and districts of any US city! And, many of these neighborhoods have large concentrations of different ethnic groups, making it like a trip around the globe without ever leaving the Midwest city.

How much time should I spend in Chicago?

You can see the best of Chicago on a long weekend trip, but a week is an ideal amount of time if you're really wanting to explore the city deeper. You can see the main highlights on a long weekend trip, though. To maximize your time, sign up for city tours and utilize the 'L', or metro system.

What food is Chicago known for?

It would be remiss of me to mention the food of Chicago and not start off with deep-dish pizza! Originating at Pizzeria Uno in 1943, this style of pizza is beloved by residents of the Windy City and it has become Chicago's most iconic dish! Some other foods to try when visiting are Chicago style hot dogs (made famous during the Great Depression), Italian beef, and Chicago BBQ. You can also dive into the city's Eastern European history with some tasty perogies and potato pancakes.

What is the best way to get around Chicago?

While renting a car may be the most ideal option for those looking to take day trips, Chicago is a very well-connected city that lends itself to walking and public transportation!

You will find plenty of taxis, public buses, and bike sharing options within Chicago. The city is also home to the L-train, or the city's metro operated by the Chicago Transit Authority. The L-train stands for 'elevated train' and it serves over 140 stations on its 8 train lines.

What are the best months to visit Chicago?

Winter can be brutally cold in Chicago (and snowy), making the best time to visit the city summer (or the shoulder season). The summers in Chicago are never exceptionally hot and the greenery makes the area pleasant and inviting. Lake Michigan also offers plenty of opportunities during the summer months, as well. You can swim on its beaches or take a boat out into the lake.

What are the best neighborhoods to visit in Chicago?

Chicago has some of the most dynamic neighborhoods of any city I have ever been in! Every one has something interesting and unique to offer! Some of the most popular neighborhoods are Wicker Park (lots of cool bars and cafes), Logan Square (young professionals and hip establishments), Andersonville (known for its Swedish history and Midsommarfest), Pilsen (known for its art scene), Ukrainian Village (lots of Ukrainian history, art museums, and businesses), Lincoln Square (German history with many Bavarian bakeries, etc), and more.

What are the best neighborhoods for food?

Lincoln Park is a favorite Chicago district for food lovers! One thing that the neighborhood is famous for is its brunch options! You can find many international restaurants here - but brunch is a big deal in Lincoln Park and you can find everything from vegetarian brunch options to French toast flights and DIY mimosas!

Another area of the city known for its trend-setting food options is the West Loop. The West Loop is located in the former meatpacking district and now has so much to offer food lovers - from fine dining restaurants to celebrity chefs opening up new concepts to Chicago residents.

If you love Mexican food - head to Pilsen and indulge in some of the city's best Mexican restaurants.

What are the best neighborhoods for shopping?

Chicago is a shopper's paradise and you will find delightful shopping everywhere! Michigan Avenue is the city's most famous shopping thoroughfare - with shops lining the streets and mega malls located along one of the city's busiest streets. The Shops at North Bridge and the 900 North Michigan Shops are some of the places to check out when there. Beyond Michigan Avenue, you can find great shopping on Armitage Avenue in Lincoln Park and cool vintage finds on Belmont Avenue at The Belmont Army. There are also many other second-hand shops and indie stores if you head east on Belmont.

What neighborhood should I stay in when I visit Chicago?

If you're a first-time visitor to Chicago, you will want to stay downtown and near many of the main sights and museums. Other good and safe options are Lakeview, The Loop, and Lincoln Park. All are well connected by public transportation. However, if you're looking for a more 'local' experience, check out hotel options in Logan Square, Lincoln Square, and Wicker Park. There are plenty of food options and hip bars and hang out in!

What's are 4 best tips for a person traveling to Chicago?

1) Don't let yourself get overwhelmed. This is the US' third most populous city and it is a lot to take in! Plan your trip ahead and then try to stay in one area and explore it deeply. You can save additional sights and areas for a future trip.

2) Heading to Chicago in winter? Bundle up! They don't call it the Windy City for nothing! It is cold, windy, and snowy! But, you will still find plenty to do in the city during the winter months that it is always worth a visit!

3) If you're visiting different neighborhoods, research the history of the place and find pieces of those history throughout. For example, if you're visiting Andersonville, you will quickly realize that it has extensive Swedish history. Stop into Swedish bakeries and shops and see how this culture has meshed together with Chicago's throughout the years. It truly is one of the things that makes the Midwest city so unique!

4) Take the L-train! This transport option is cheap, efficient, and the best way to get around the city. You can save so much money by avoiding driving around and parking and just taking the L around.

What should people avoid doing in Chicago?

Avoid thinking that this city is similar to Los Angeles and New York. Chicago retains that Midwestern 'down-to-earth' charm that can get lost a bit on the coasts. The city is sports-centric and bars are super social and friendly. Be sure to go in ready to meet people and make some new friends along the way!

Another thing to avoid is eating at the chain restaurants. While these places are predictable and offer a 'secure' experience - Chicago has some insanely good food options and there is no better way to learn about the city than through its food!

What are your top 5 favourite GetYourGuide experiences in Chicago?

1) Chicago River: 1.5-Hour Guided Architecture Cruise

2) Chicago: Willis Tower Skydeck and The Ledge Ticket

3) Chicago: Gangsters and Ghosts 2-Hour Walking Tour

4) Chicago Lakefront: Seadog Speedboat Ride

5) Chicago: Favorite Foods Guided Walking Tour

What is one thing that surprised you about Chicago?

I have been to Chicago more times than I can count, but the one thing that always surprises me is how friendly everyone is! Big cities tend to be a little unfriendly but Chicago is the absolute opposite. Every time I head there, I meet new people and make new connections and it is difficult to leave. I wouldn't be surprised if I ended up moving there one day and calling the Windy City my home.

What are the best annual events in Chicago?

Chicago has several events annually and one of the city's most popular is the Taste of Chicago, the largest food festival in the world! You'll find a lot of live music, food, and more! It is a must-visit summer festival in Chicago. The city also has several music festivals not only dedicated to popular bands, but also different genres of music. You can head to the Chicago Jazz Festival or the Chicago Blues Festival and see how both styles of music have made an impact on Illinois' largest city.

Explore Chicago

Read our complete guide to Chicago, or discover the city's best experiences.

What people are saying about Chicago

Overall rating

4.6
(16,697 reviews)

It's great for eSIM-enabled cell phones. I had no problems unlocking it. I had a normal SIM card in my German cell phone and have now also activated the eSIM for vacation in America. Works great. Thanks

We enjoyed the tour very much, learned a lot. Karinna was knowledgeable and friendly. We stopped half way through for a break at Palmer House which was a plus.

Loved the tour! Fun cute way to get to know the city :) And Sarah our tour guide was super informative fun and engaging!

Guide was very nice snd funny. This gave another view of the city and it was nice!

Guide was excellent and upbeat!!! Very informative tour