36 Hours In Chicago, Illinois

36 hours in chicago

One of the largest and most prominent cities in the United States is Chicago, which lies next to Lake Michigan. It’s also a popular tourist destination due to its many excellent landmarks such as Blackstone Library, Clarence Buckingham Memorial Fountain and Garden, and the Chicago Board of Trade Building. Furthermore, Chicago has many popular attractions where one can have a good time. These include Millennium Park, that’s great for relaxing and people watching, Purple Pig - for its delicious pork dishes and wine, and the Green Mill - for the amazing live jazz performances. Check out our comprehensive guide of how you should spend 36 hours in Chicago, Illinois, the USA, and plan your upcoming trip accordingly.

Day 1: Afternoon

Spend some time at Millennium Park

Skating by the Bean - Millennium Park - Chicago - Illinois - USA (32164006083)
Source: Photo by Wikimedia Commons user Adam Jones used under CC BY-SA 2.0

Start your exploration of Chicago from the world-renowned Millennium Park. It’s the perfect place for relaxing and people watching, and possibly catching a concert if you arrive at the right time. Also, this park includes several facilities such as the AT&T Plaza and Cloud Gate, Boeing Galleries, BP Pedestrian Bridge, Chase Promenade, Crown Fountain, Harris Theater, Exelon Pavilions, Jay Pritzker Pavilion, Lurie Garden, McCormick Tribune Plaza & Ice Rink and Park Grill, McDonald’s Cycle Center, Nichols Bridgeway, and Wrigley Square.

Millennium Park

Address: 201 E Randolph St, Chicago, IL 60602, United States

Website: Millennium Park

Opening hours: 6am - 11pm (daily)

Check out artwork at the Art Institute of Chicago

Art Institute of Chicago from south
Source: Photo by Wikimedia Commons user Beyond My Ken used under CC BY-SA 4.0

One of the largest, oldest, and most significant art museums in the United States is none other than the Art Institute of Chicago. Founded in the late 19th century, this museum boasts a wide range of important works and exhibitions from luminaries such as El Greco, Pablo Picasso, and Vincent van Gogh, to name a few. There’s also plenty of African, Egyptian, and contemporary artworks on exhibit that only help widen the appeal of this amazing museum.

Art Institute of Chicago

Address: 111 S Michigan Ave, Chicago, IL 60603, United States

Website: Art Institute of Chicago

Opening hours: Thu - Fri: 1pm - 8pm; Sat - Mon: 11am - 6pm (closed on Tue & Wed)

Price: 19 - 29 USD

Day 1: Evening

Have a delicious dinner at Purple Pig

37 Steakhouse & Bar
Source: Photo by Wikimedia Commons user Stillfoods inc. used under CC BY-SA 3.0

The Purple Pig is a popular Mediterranean restaurant that boasts a comprehensive and evolving pork and wine menu. We recommend their delicious Koji-Rubbed Prime New York Strip, Pork Gyro, and Ricotta Gnocchi. And, do try out their Douloufakis, Fattoria Sardi, or Pico Maccario wine, and also order a refreshing draft beer from the many microbrewery brands on offer. The restaurant also offers a curbside pickup and delivery service for your convenience.

Purple Pig

Address: 444 Michigan Ave, Chicago, IL 60611, United States

Website: Purple Pig

Opening hours: 11:30am - 11pm (daily)

Enjoy cocktails and a magnificent city view at The Signature Room

Cocktail-Bar (Kleines Phi) in Hamburg
Source: Photo by Wikimedia Commons user Achim Schleuning used under CC BY-SA 4.0

The Signature Room offers patrons an upscale dining and drinking experience. Here, you can order tasty cocktails such as a Lime-Mint Refresher, PAMA Kiss, and Strawberry Smoothie. But if cocktails aren’t your thing, you can also order a Hennessy V.S.O.P, Moët & Chandon, or Sauvignon Blanc, and enjoy your drink while taking in those stunning panoramic views of Chicago.

The Signature Room at the 95th®

Address: 875 N Michigan Ave, Chicago, IL 60611, United States

Website: The Signature Room at the 95th®

Opening hours: Sun - Thu: 5pm - 10pm; Fri - Sat: 5pm - 11pm

Day 1: Night

Spend the night listening to Jazz at The Green Mill

Green Mill Cocktail Lounge exterior
Source: Photo by Wikimedia Commons user Kenneth C. Zirkel used under CC BY-SA 4.0

End your first night in Chicago by visiting one of its most popular jazz clubs, namely, the Green Mill. Here, you’ll be able to order delicious cocktails while listening to late-night jams by famous and local jazz artists. Furthermore, you’ll have an opportunity to mix and mingle with some of Chicago’s most fervent music lovers and party-goers.

The Green Mill

Address: 4802 N Broadway, Chicago, IL 60640, United States

Website: The Green Mill

Opening hours: Mon - Fri: 12pm - 4am; Sat: 12pm - 5am; Sun: 11am - 4am

Price: 10 - 15 USD

Day 2: Morning

Have a late breakfast at Wildberry Pancakes & Cafe

Breakfast! (15506456527)
Source: Photo by Wikimedia Commons user Mark Bonica used under CC BY 2.0

Nothing beats a hearty breakfast to start the day on a good note. But nothing compares to munching down on delicious pancakes at one of Chicago’s best breakfast-lunch cafes. At Wildberry Pancakes & Cafe, you can order their mouthwatering Chocolate Chip Banana, Key Lime Pie, or Signature Berry Bliss pancakes. Also, you should try out their amazing BBQ Chicken Tortilla Salad, Brisket Grilled Cheese sandwich, and Pure Belgian waffles.

Wildberry Pancakes & Cafe

Address: Prudential Plaza, 130 E Randolph St, Chicago, IL 60601, United States

Website: Wildberry Pancakes & Cafe

Opening hours: 7am - 2pm (daily)

Tour the Field Museum of Natural History

Field Museum of Natural History
Source: Photo by Wikimedia Commons user Joe Ravi used under CC BY-SA 3.0

The Field Museum of Natural History is the ideal place to learn about our ancient past. There are a plethora of exhibits here, many of which are interactive. And these are perfectly suited for younger participants who want to know more about subject matter that’s beyond the scope of the classroom. A few exhibitions that you can look forward to include; the Apsáalooke Women and Warriors, Cyrus Tang Hall of China, Inside Ancient Egypt, Plants of the World, and Robert R. McCormick Halls of the Ancient Americas, to name a few.

Field Museum

Address: 1400 S Lake Shore Dr, Chicago, IL 60605, United States

Website: Field Museum

Opening hours: Thu - Mon: 9am - 5pm (closed on Tue & Wed)

Price: 17 - 40 USD

Day 2: Afternoon

Visit Navy Pier and ride the Centennial Wheel

Navy Pier from the shoreline
Source: Photo by Wikimedia Commons user David Bjorgen used under CC BY-SA 2.5

Spend some quality time at Chicago’s premier waterfront, namely, Navy Pier. It’s a popular destination for both locals and out-of-town visitors due to the large variety of attractions, eateries, and events that you will find here. But you’ll probably be visiting for the giant Centennial Wheel that’s worth riding for the amazing views of the city.

Navy Pier

Address: 600 E Grand Ave, Chicago, IL 60611, United States

Website: Navy Pier

Opening hours: Mon - Thu: 10am - 10pm; Fri - Sun: 10am - 12am

Price: 15 USD

Head to Shedd Aquarium

20070110 Shedd Aquarium
Source: Photo by Wikimedia Commons user TonyTheTiger used under CC BY-SA 3.0

Most major cities have at least one aquarium that people can visit and view their undersea friends. At Chicago’s impressive Shedd Aquarium, one is exposed to a wide range of excellent exhibitions, facilities, and tours. These include the Abbott Oceanarium, Caribbean Reef, Polar Play Zone, Wild Reef, and exterior gardens and terraces.

Shedd Aquarium

Address: Museum Campus, 1200 S Lake Shore Dr, Chicago, IL 60605, United States

Website: Shedd Aquarium

Opening hours: Mon: 9am - 3pm; Tue - Sun: 9am - 5pm

Price: 15 - 40 USD

Wind down at Deep Ocean Cafe

Chicago style hot dogs (13340033944)
Source: Photo by Wikimedia Commons user jeffreyw used under CC BY 2.0

It can get tiring checking out all those amazing exhibits at the aquarium. Fortunately, there are some good eateries on the premises, such as Deep Ocean Cafe. Here, you can order several tasty treats, which include Dippin’ Dots ice cream, hot dogs, nachos, popcorn, pretzels, and refreshments.

Deep Ocean Cafe

Address: Shedd Aquarium, 1200 S Lake Shore Dr, Chicago, IL 60605, United States

Website: Deep Ocean Cafe

Opening hours: Mon - Thu: 10am - 10pm; Fri - Sun: 10am - 12am

Day 2: Evening

Enjoy a dinner at The Magnificent Mile

20070509 Foot of Magnificent Mile
Source: Photo by Wikimedia Commons user TonyTheTiger used under CC BY-SA 3.0

As you near the end of your excursion in Chicago, it makes sense to have your last dinner at The Magnificent Mile. This is an upscale and vibrant neighborhood that features a ton of boutique hotels, luxury stores, and trendy restaurants. Several of the leading restaurants in the area include Althea, Bandera, Frankie’s Scaloppine, Labriola Chicago, Michael Jordan’s Steak House, Reviver, and Spiaggia, to name a few.

The Magnificent Mile

Address: Near North Side, Chicago, IL, United States

Opening hours: 24 hours (daily)

Day 2: Night

Catch some live music at Kingston Mines

Ledfoot Gothic Blues Live in Concert 2012 - 2
Source: Photo by Wikimedia Commons user Rainer Mueck used under CC BY-SA 3.0

Photo is only for illustrative purposes

Kingston Mines has been in business since 1968 and has become a favorite haunt for Chicago’s blues and music lovers. The venue features two stages where bands perform live, and there’s ample space for those who wish to dance. Furthermore, there’s some delicious pub grub on the menu, such as Chicken Strips & Fries, Pecan Pie, and Spicy Buffalo.

Kingston Mines

Address: 2548 N Halsted St, Chicago, IL 60614, United States

Website: Kingston Mines

Opening hours: Mon - Thu: 7:30pm - 12am; Fri - Sat: 7pm - 12am; Sun: 6pm - 12am

Price: 12 - 15 USD

A plethora of attractions to fill 36 hours

There’ll never be a dull moment in Chicago due to the many amazing attractions found here. Whether you’re looking for an art museum, an aquarium, a breakfast cafe, a cocktail bar, a live music venue, or a recreational park, you won’t be disappointed by what you’ll come across.

Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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