4-Day Chicago Adventure: Iconic Attractions, River Tour & Culinary Delights

Day 1: Travel & Dinner

Detroit, MI to Kalamazoo, MI on June 19, 2025

2:00pm

Depart Detroit

Start your drive from Detroit heading towards Chicago with an exciting food and brewery stop planned en route.
USD0, 4h0m

6:30pm

Dinner at Bell’s Brewery - Kalamazoo, MI

Enjoy craft beers and delicious dishes at Bell’s Brewery, famous for its flavorful brews. It's a perfect spot to relax and refuel before continuing to Chicago.
USD20-40, 1h30m

8:00pm

Drive to Chicago

Continue your journey to Chicago and check in at Hyatt Regency Chicago for a comfortable stay.
USD0, 3h0m
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Day 2: Iconic Chicago

Chicago, IL on June 20, 2025

8:00am

Breakfast at Wildberry Pancakes and Cafe

Start your day with a hearty breakfast at this popular spot known for its creative pancakes and delicious morning fare, located near Millennium Park.
USD15-25, 1h0m

9:30am

Visit Willis Tower Skydeck

Explore the Skydeck at Willis Tower and step out onto The Ledge for breathtaking views of Chicago and beyond. Opens at 9 am.
USD30, 1h30m

11:30am

Walk and Explore Millennium Park

Discover the Cloud Gate ('The Bean'), Crown Fountain, and Lurie Garden in this iconic urban park. It's a great spot for photos and relaxation.
USD0, 1h0m

12:30pm

Lunch at Giordano’s

Savor Chicago’s famous deep-dish pizza at Giordano’s, just a short walk from Millennium Park, open from 11:30 am.
USD20-30, 1h0m

2:00pm

Visit Navy Pier

Enjoy the lakefront views, ride the Centennial Wheel, or explore museums and shops on Navy Pier. Open daily from 10 am to 10 pm.
USD15-25, 2h0m

6:30pm

Dinner at 'The Purple Pig'

Experience Mediterranean-inspired cuisine in a lively atmosphere on Michigan Avenue. Great for sharing plates after a full day of sightseeing.
USD40-60, 1h30m
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Day 3: Culture & Nature

Chicago, IL on June 21, 2025

8:30am

Breakfast at Yolk

Enjoy creative breakfast favorites and great coffee at this local favorite near the Museum Campus.
USD15-25, 1h0m

9:30am

Visit Shedd Aquarium

Explore one of the world’s largest indoor aquariums featuring aquatic life from around the globe. Opens at 9 am.
USD40, 2h30m

12:15pm

Visit Field Museum

Discover natural history highlights including Sue the T. rex, and cultural exhibits. Opens at 9 am.
USD40, 2h0m

2:30pm

Lunch at Museum Campus Café

Quick and convenient dining option within the Museum Campus, perfect for refueling between museum visits.
USD15-20, 1h0m

4:00pm

Chicago River Architecture Tour

Take a scenic boat tour to admire Chicago’s architectural marvels along the Chicago River. Afternoon tours usually run until 5 pm.
USD50, 1h30m

6:30pm

Dinner at Lou Malnati’s Pizzeria

Indulge in another classic Chicago deep-dish pizza experience at this highly regarded pizzeria, open until 10 pm.
USD20-30, 1h0m
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Day 4: Art & Departure

Chicago, IL on June 22, 2025

8:00am

Breakfast at Intelligentsia Coffee

Grab artisanal coffee and light breakfast items at this famous Chicago coffeehouse near the Art Institute.
USD10-15, 1h0m

9:00am

Visit Art Institute of Chicago

Explore one of the top art museums featuring a diverse collection from Impressionist masterpieces to contemporary art. Opens at 10 am, consider arriving early for tickets.
USD25, 2h30m

12:00pm

Lunch at The Gage

Enjoy upscale American cuisine with a cozy atmosphere near Millennium Park, open from 11:30 am.
USD25-40, 1h0m

1:30pm

Pack and check out

Return to Hyatt Regency Chicago to pack your things and prepare for departure.
USD0, 1h0m

2:30pm

Depart Chicago for Detroit

Begin your comfortable drive back to Detroit, concluding your great Chicago trip.
USD0, 5h0m
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