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Chicago Highlights Itinerary from Detroit | June 19-22, 2025

Viewed by 125 travelers

Day 1: Arrival and Dinner

Detroit to Chicago, USA on June 19, 2025

2:00pm

Departure from Detroit

Leave Detroit by car at 2pm to travel to Chicago, approximately a 4.5-5 hour drive.
USD0, 5h0m

7:30pm

Dinner at Bell's Brewery

Stop at Bell's Brewery for dinner, enjoying their craft beers and fresh brewery fare in a relaxed atmosphere before continuing to Chicago.
USD30, 1h0m

9:00pm

Check-in at Hyatt Regency Chicago

Arrive in Chicago and check into the Hyatt Regency Chicago, centrally located and perfect for exploring the city.
USD0, N/A
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Day 2: City Landmarks and Art

Chicago, USA on June 20, 2025

8:30am

Breakfast at Wildberry Pancakes & Cafe

Start your day with a delicious breakfast at Wildberry Pancakes & Cafe near Millennium Park, known for its pancakes and fresh fruit dishes.
USD20, 1h0m

10:00am

Visit Willis Tower Skydeck

Explore the Willis Tower Skydeck's spectacular views from one of the tallest buildings in the western hemisphere. Open 9am-10pm.
USD30, 1h0m

12:00pm

Lunch at Lou Malnati's Pizzeria

Enjoy authentic Chicago deep dish pizza at Lou Malnati's, a classic spot for the city’s famous pizza styles.
USD25, 1h0m

1:30pm

Millennium Park visit

Walk around Millennium Park to see iconic features such as Cloud Gate (The Bean) and Lurie Garden, open all day, free entry.
USD0, 1h0m

3:00pm

The Art Institute of Chicago

Visit the Art Institute, home to world-class collections of Impressionist and modern art. Open from 10:30am to 5:00pm.
USD25, 2h0m

6:00pm

Dinner at The Signature Room at the 95th

Dine with a view at The Signature Room atop the John Hancock Center, featuring elegant dishes and panoramic Chicago views. Open until 10pm.
USD50, 1h30m
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Day 3: Museum & River Tour

Chicago, USA on June 21, 2025

8:00am

Breakfast at Yolk - The Loop

Fuel up at Yolk for a hearty breakfast with creative egg dishes and fresh juices before a full day of sightseeing.
USD20, 1h0m

9:30am

Shedd Aquarium

Visit the Shedd Aquarium to explore aquatic life and immersive exhibits. Opens at 9am, plan about 2-3 hours here.
USD40, 3h0m

12:30pm

Lunch at The Field Bistro inside Field Museum

Have a casual lunch at The Field Bistro inside the Field Museum before starting your visit. Museum opens at 9am to 5pm.
USD20, 1h0m

1:30pm

Field Museum of Natural History

Discover natural history wonders including Sue, the T-Rex skeleton, numerous cultural artifacts, and engaging exhibits.
USD40, 2h30m

4:00pm

Chicago River Architecture Tour

Take a scenic guided boat tour along the Chicago River to admire the city’s famous architecture. Tours run until early evening, approx. 90 minutes.
USD50, 1h30m

6:30pm

Dinner at Giordano's

Enjoy classic Chicago stuffed deep dish pizza at Giordano's, a trusted and popular pizzeria with many locations.
USD25, 1h0m
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Day 4: Leisure & Departure

Chicago to Detroit, USA on June 22, 2025

8:00am

Breakfast at Do-Rite Donuts & Chicken

Have a casual breakfast with gourmet donuts and coffee at Do-Rite, perfect for a quick but delicious start.
USD15, 0h45m

9:00am

Leisure walk through Millennium Park or shopping

Enjoy a relaxed morning stroll around Millennium Park or nearby shopping streets like State Street to pick up souvenirs.
USD0, 1h0m

11:00am

Check out from Hyatt Regency Chicago

Prepare for departure from the hotel and begin the journey back to Detroit.
USD0, N/A
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