Chicago

Chicago is a historical and architectural gem. The playground of Frank Lloyd Wright, it's home to many examples of modernist architecture. The dining experiences in Chicago are second to none, as it has some of the best restaurants in the world, including a plethora of Michelin-starred restaurants. And Chicago is home to some of the best comedy clubs in the world, including The Second City, Improv Olympic and Laugh Factory.
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Featured guides

Multi-city stops

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Top places to visit

1Millennium Park

4.8
(77628)
4.5
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Park
Sights & Landmarks
Millennium Park is an awe-inspiring public space in Chicago that features an impressive collection of world-class architecture and sculptures. The park is home to the Jay Pritzker Pavilion, one of the world's largest outdoor sculptures by British artist Anish Kapoor and Cloud Gate, one of the world's largest pieces of public sculpture.

2The Art Institute of Chicago

4.8
(30734)
5.0
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expensive
Museum
Art museum
The Art Institute of Chicago is a world-renowned art museum with over 3000 pieces spanning 5000 years of artistic innovation. The museum is located in Grant Park on the city's front lawn and features one of the largest school of architecture in the world.
111 S Michigan Ave, Chicago, IL 60603, USAhttp://www.artic.edu/

3Cloud Gate

4.7
(28061)
4.5
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Sculpture
Sights & Landmarks
A sculpture of a bean located in Millennium Park in Chicago, Cloud Gate is an easily Instagrammable spot that can be photographed from close up or further back with the skyline of Chicago as the backdrop.

4Skydeck Chicago

4.5
(28711)
4.5
(17832)
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Observation deck
Sights & Landmarks
Located on the 103rd floor of the former Sears Tower, Skydeck Chicago provides visitors with breathtaking views of four states. The unique viewing platform The Ledge lies 4ft outside the building dimensions and offers brave visitors unrivaled views over the city. With museum-quality exhibits and a 60-second ride up to the 103rd floor, Skydeck Chicago is a must-see attraction in Chicago.

5Navy Pier

4.6
(72200)
4.0
(15145)
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Sights & Landmarks
Amusement center
Navy Pier is one of the most popular tourist destinations in Chicago with rides, restaurants, shops, and more. The pier juts into Lake Michigan and has an endless amount of attractions for all ages. It's a great place to spend a day with family.
600 E Grand Ave, Chicago, IL 60611, USAhttps://navypier.org/

Top places to eat

1The Purple Pig Restaurant

4.6
(5813)
4.5
(6033)
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affordable
Mediterranean restaurant
The Purple Pig Mediterranean Restaurant offers an open kitchen with chic and airy settings, as well as a wine list with a focus on French and Italian wines from various different regions. The restaurant is run by the fourth generation of restaurateurs, who were mentored by their father Jimmy Bannos (Chef/Owner of Heaven on Seven) and catapulted their expertise through training by nationally renowned chefs.
444 Michigan Ave, Chicago, IL 60611, USAhttps://thepurplepigchicago.com/

2Eataly

4.3
(4424)
4.5
(5019)
expensive
Italian restaurant
Eataly is a large Italian food and goods marketplace with four sit-down restaurants and eight quick service counters. The marketplace also has a wine bar, gelato bar, and focaccia counter with a wide selection of Italian flatbreads. The highlight of the first floor is the Gelato Bar, where freshly made gelato is ultra-creamy and intensely flavored.
43 E Ohio St, Chicago, IL 60611, USAhttps://www.eataly.com/us_en/stores/chicago/

3Wildberry Pancakes & Cafe

4.6
(7580)
4.5
(4805)
affordable
Brunch restaurant
Restaurant
Wildberry Pancakes & Cafe is a cafe located just steps away from Millennium Park in Chicago's South Loop. The cafe features a wide range of breakfast and lunch choices, with pancakes being the most popular item on the menu. The cafe is always packed with crowds of locals and tourists alike, due to the delicious pancakes that are served here. French toast is also highly recommended, as it has some amazing red velvet flavors on the menu.
130 E Randolph St, Chicago, IL 60601, USAhttps://wildberrycafe.com/prudential.php
4.7
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4.5
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very expensive
Seafood restaurant
Joe's Seafood is a seafood restaurant with specialty crab claws, served in a plush setting. The cuisine is diverse and includes steaks and chicken dishes. reservations are recommended.
4.6
(5265)
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(3797)
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very expensive
Steak house
Gibsons Bar and Steakhouse is an upscale steakhouse with a lively setting and beautiful atmosphere. They serve their lunch menu for brunch on Saturdays and Sundays, and are a favorite meeting spot for folks looking for the best brunch in Chicago.

Looking for day-by-day itineraries in Chicago?

Get inspired for your trip to Chicago with our curated itineraries that are jam-packed with popular attractions everyday! Check them out here: