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Exploring Chicago in 5 Days

Viewed by 76 travelers

Day 1: City Highlights

Chicago, USA

9:00AM

Breakfast at Wildberry Pancakes and Cafe

Start your day with delicious pancakes and local coffee before heading to Millennium Park.
Walk from Wildberry Pancakes and Cafe to Millennium Park, approximately 10 minutes.
$15, 1 hour

11:00AM

Explore Millennium Park

Visit the famous Cloud Gate sculpture, Crown Fountain, and enjoy a leisurely walk in the park.
Walk from Millennium Park to the Art Institute of Chicago, approximately 5 minutes.
$0 (park entry may have fees), 2 hours

1:30PM

Lunch at The Gage

Indulge in a hearty meal at this gastropub known for its upscale twists on comfort food.
Walk from the Art Institute of Chicago to The Magnificent Mile, approximately 15 minutes.
$30, 1.5 hours

4:00PM

Shop and Explore The Magnificent Mile

Shop at high-end stores, admire historic architecture, and maybe grab a coffee or treat.
End of day 1 in The Magnificent Mile.
$ varies, 2 hours
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Day 2: Navy Pier and Skyscrapers

Chicago, USA

10:00AM

Navy Pier

Spend the morning at Navy Pier, enjoying the rides, shops, and lake views.
Walk from Navy Pier to the Chicago Riverwalk, approximately 15 minutes.
$0 (rides and attractions may have fees), 2 hours

1:00PM

Lunch at Riva Crabhouse on Navy Pier

Dine on fresh seafood with views of Lake Michigan at this popular restaurant.
Walk from the Chicago Riverwalk to Willis Tower, approximately 20 minutes.
$40, 1.5 hours

3:30PM

Willis Tower Skydeck

Experience the glass-bottomed Skydeck and take in panoramic views of the city.
End of day 2 at Willis Tower.
$25, 1.5 hours
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Day 3: Zoo, Baseball, and Comedy

Chicago, USA

9:00AM

Breakfast at The Bongo Room

Start your day with creative breakfast dishes at this popular spot in Wicker Park.
Travel from breakfast to Lincoln Park Zoo by taxi, approximately 20 minutes.
$20, 1 hour

11:00AM

Visit Lincoln Park Zoo

Explore the free zoo and see animals from around the world in a beautiful setting.
Travel from Lincoln Park Zoo to Wrigley Field by taxi or public transportation, approximately 15 minutes.
$0, 2 hours

2:00PM

Lunch at Lucky's Sandwich Company

Try one of the famous overstuffed sandwiches at this casual eatery near Wrigley Field.
Travel from Wrigley Field to Second City Comedy Club by taxi or public transportation, approximately 10 minutes.
$15, 1.5 hours

4:30PM

Enjoy a Comedy Show at Second City

Laugh the evening away with improv and sketch comedy at this iconic venue.
End of day 3 at Second City Comedy Club.
$35, 2 hours
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Day 4: Museums and Evening Fun

Chicago, USA

10:00AM

Visit Museum Campus

Explore the Field Museum, Shedd Aquarium, and Adler Planetarium in this museum complex.
Travel from Museum Campus to Navy Pier by taxi or public transportation, approximately 10 minutes.
$50 (for all museums), 3 hours

2:00PM

Afternoon Activities at Navy Pier

Enjoy more of Navy Pier's attractions or relax by the lake for the afternoon.
End of day 4 at Navy Pier.
$ varies, 2 hours
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Day 5: Green Spaces and Cultural Sites

Chicago, USA

9:00AM

Explore Garfield Park Conservatory

Stroll through lush indoor gardens and admire the variety of plant species at this conservatory.
Travel from Garfield Park Conservatory to Chicago Cultural Center by taxi or public transportation, approximately 25 minutes.
$5, 1.5 hours

11:30AM

Visit Chicago Cultural Center

Marvel at the stunning architecture and cultural exhibitions in this historic building.
Travel from Chicago Cultural Center to Skydeck Chicago by taxi or public transportation, approximately 15 minutes.
$0, 2 hours
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