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
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.
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
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
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Day 1: Evening
Have a delicious dinner at Purple Pig
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.
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
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
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
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
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.
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
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.
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
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.
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
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
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
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.
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.
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