5-Day Immersive Chicago Itinerary with Local Dining and Iconic Sights

Day 1: Local Start & Millennium Park

Chicago, USA on July 13, 2025

8:30am

Breakfast at Coffeebike South Side

Enjoy a local start with specialty coffee and pastries at this nearby mobile coffee shop, perfect for energising your first morning in Chicago.
USD6, 0h30m

10:00am

Visit Millennium Park

Explore Chicago’s iconic Millennium Park, home to the famous Cloud Gate (The Bean) sculpture and stunning gardens. Open daily from 6am to 11pm.
Free, 2h0m

12:30pm

Lunch at Giordano’s

Taste Chicago’s deep-dish pizza at Giordano’s, located a short walk from Millennium Park, a classic foodie experience. Open 11am–10pm.
USD25, 1h30m

2:30pm

Art Institute of Chicago

Spend your afternoon at the Art Institute, admiring extensive art collections from ancient to modern works. Open 10:30am–5pm on Sundays.
USD25, 2h0m

5:00pm

Return to South Cornell area

Take public transit back to your accommodation to rest and refresh before dinner.
USD5, 1h0m

7:00pm

Dinner at Valois Restaurant

Experience a famous Chicago cafeteria-style eatery known for diverse Southern-inspired dishes, open late until 10pm, close to your accommodation.
USD20, 1h30m
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Day 2: Museum Campus & Navy Pier

Chicago, USA on July 14, 2025

8:00am

Breakfast at Yolk

Start your day with a hearty breakfast at Yolk, known for its creative egg dishes and fresh ingredients. Open 7am–3pm.
USD15, 1h0m

9:30am

Field Museum of Natural History

Delve into the natural world with fascinating exhibits such as Sue the T-Rex at the Field Museum. Open 9am–5pm.
USD26, 2h30m

12:30pm

Lunch at Museum Campus Café

Grab a light lunch at the café on-site within Museum Campus, convenient for continuing your afternoon activities.
USD15, 1h0m

1:30pm

Shedd Aquarium

Explore the vibrant underwater world and marine life exhibits at Shedd Aquarium, open 9am–5pm.
USD35, 2h0m

4:00pm

Walk to Navy Pier

Take a scenic walk along the lakefront to Navy Pier, perfect for harbour views and entertainment.
Free, 1h0m

5:00pm

Explore Navy Pier

Enjoy the rides, shops and entertainers on Navy Pier, which stays open until 11pm, with plenty of evening atmosphere.
Variable, 2h0m

7:30pm

Dinner at Riva Crabhouse on Navy Pier

Savour fresh seafood with lakefront views at Riva Crabhouse, open for dinner until 10pm.
USD40, 1h30m
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Day 3: Architecture & Shopping

Chicago, USA on July 15, 2025

8:00am

Breakfast at Wildberry Pancakes and Cafe

Indulge in one of the best breakfasts in Chicago featuring pancakes, waffles, and fresh fruit. Open 7am–3pm.
USD15, 1h0m

9:30am

Chicago Architecture Foundation River Cruise

Discover Chicago’s iconic architecture on a 90-minute river cruise offered by the Chicago Architecture Center. Cruises run from 10am–4pm.
USD50, 1h30m

11:30am

Walk Magnificent Mile

Explore Michigan Avenue’s Magnificent Mile shopping district, a stretch filled with boutiques and landmarks, open all day.
Free, 2h0m

1:30pm

Lunch at The Purple Pig

Eat Mediterranean-inspired small plates in a lively environment on Magnificent Mile. Open 11:30am–10pm.
USD30, 1h30m

3:00pm

Visit 360 Chicago Observation Deck

See the city from above at 360 Chicago (John Hancock building observation deck) open 10am–11pm.
USD30, 1h0m

5:00pm

Return to accommodation

Head back to your accommodation for a rest and freshen up before dinner.
USD5, 1h0m

7:00pm

Dinner at Promontory

Enjoy upscale dinner with contemporary American dishes near your accommodation, open until 10pm.
USD50, 1h30m
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Day 4: Chicago Neighbourhoods & Jazz

Chicago, USA on July 16, 2025

8:30am

Breakfast at South Cornell Local Café

Start your last morning with a casual breakfast choice near your stay, enjoying local vibes.
USD10, 0h45m

9:30am

Visit Hyde Park & Museum of Science and Industry

Explore Hyde Park neighbourhood and visit the Museum of Science and Industry. Open 9:30am–4pm.
USD22, 2h30m

12:30pm

Lunch at Medici on 57th

Enjoy a variety of sandwiches and cuisine at this popular Hyde Park restaurant, open 11am–10pm.
USD20, 1h0m

2:00pm

Walk Jackson Park and Botanical Gardens

Discover the peaceful lakeside parks and gardens nearby, perfect for a relaxing afternoon walk.
Free, 1h30m

4:00pm

Return to accommodation

Head back to your accommodation to prepare for your final evening.
USD5, 1h0m

7:30pm

Dinner and live jazz at Andy’s Jazz Club

Experience authentic Chicago jazz music combined with dinner at Andy’s Jazz Club, open until midnight.
USD40, 2h30m
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Day 5: Departure

Chicago, USA on July 17, 2025

5:30am

Checkout and Transit to Airport

Early morning checkout and travel to Chicago O’Hare or Midway Airport by taxi or rideshare for your departure flight.
USD40, 1h30m
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