Comprehensive 7-Day Chicago Itinerary: Exploring the Windy City

Day 1: Introduction to Downtown

Chicago, USA on July 12, 2025

8:00am

Breakfast at Wildberry Pancakes and Cafe

Start your day with signature pancakes and fresh coffee at this popular downtown spot, open from 7am to 3pm.
USD20, 1h

9:30am

Millennium Park Visit

Explore the iconic Cloud Gate sculpture (The Bean) and enjoy the beautiful gardens and fountains in this central city park.
Free, 1h30m

11:00am

Art Institute of Chicago

Visit this world-renowned art museum featuring collections from Impressionist to modern art; it opens at 10:30am and closes at 5pm.
USD25, 2h

1:30pm

Lunch at Giordano's

Enjoy Chicago’s famous deep-dish pizza at this classic Italian-American restaurant located downtown.
USD25, 1h

3:00pm

Chicago Architecture River Cruise

Take a 90-minute cruise along the Chicago River to learn about the city’s famous architecture; tours run through the afternoon.
USD50, 1h30m

6:00pm

Dinner at The Purple Pig

Dine on Mediterranean-inspired small plates with great wine options in this lively downtown venue.
USD40, 1h30m
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Day 2: Museum Campus & South Side

Chicago, USA on July 13, 2025

8:30am

Breakfast at Goddess and the Baker

Start your day with fresh pastries and organic coffee; opens at 7am near Museum Campus.
USD18, 1h

10:00am

Shedd Aquarium Visit

Explore one of the largest indoor aquariums in the world with diverse marine life; open 9am-5pm.
USD40, 2h

12:30pm

Lunch at Museum Campus Terrace

Grab a light bite at this convenient spot with views of Lake Michigan.
USD20, 1h

2:00pm

Field Museum of Natural History

Discover ancient fossils and cultural exhibits in this expansive museum; open 9am-5pm.
USD35, 2h

4:30pm

Relax at Northerly Island Park

Enjoy a picturesque lakefront park perfect for a calming stroll beside Lake Michigan.
Free, 1h

6:30pm

Dinner at Mercat a la Planxa

Experience Spanish tapas and seafood in an elegant setting near the South Loop.
USD45, 1h30m
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Day 3: Lincoln Park & North Side

Chicago, USA on July 14, 2025

8:00am

Breakfast at Ann Sather

Famous for Swedish cinnamon buns, open from 6:30am in Lincoln Park area.
USD15, 1h

9:30am

Lincoln Park Zoo

Visit this historic and free zoo with a variety of animals, open 10am to 5pm.
Free, 2h

12:00pm

Lunch at Café Ba-Ba-Reeba!

Enjoy authentic Spanish tapas in a lively north side restaurant.
USD30, 1h

1:30pm

Chicago History Museum

Explore Chicago’s rich history with engaging exhibits; opens 9:30am-4:30pm.
USD20, 1h30m

3:30pm

Stroll along Lakefront Trail

Appreciate scenic views of Lake Michigan on this popular pedestrian and bike path.
Free, 1h30m

6:00pm

Dinner at Alinea

Experience one of Chicago’s finest Michelin-starred tasting menus with advance booking.
USD250, 2h
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Day 4: West Loop Exploration

Chicago, USA on July 15, 2025

8:30am

Breakfast at The Bongo Room

Known for decadent pancakes and creative breakfast dishes, open from 8am.
USD20, 1h

10:00am

Visit Fulton Market District

Explore street art, boutique shops, and the lively market scene in this trendy area.
Free, 2h

12:30pm

Lunch at Lyonnais

Delight in French bistro fare from celebrity chef Stephanie Izard, open for lunch weekdays.
USD35, 1h

2:00pm

Visit Chicago History Museum’s West Loop Exhibits or explore local galleries

Gain more insight into Chicago’s culture or enjoy art galleries exhibiting contemporary works.
Variable, 2h

5:00pm

Coffee and relax at Sawada Coffee

Try Japanese-inspired coffee and beats in a cool West Loop café.
USD10, 1h

7:00pm

Dinner at Girl & The Goat

Enjoy innovative American cuisine at one of Chicago’s most popular restaurants; reservations recommended.
USD60, 2h
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Day 5: Hyde Park Highlights

Chicago, USA on July 16, 2025

8:30am

Breakfast at Medici on 57th

Popular neighbourhood spot serving American breakfast classics and coffee, open from 7am.
USD18, 1h

10:00am

Visit the University of Chicago Campus

Explore this historic campus with beautiful Gothic architecture and visit the Smart Museum of Art.
Free, 2h

12:30pm

Lunch at Valois Restaurant

Enjoy casual cafeteria-style American comfort food beloved by locals.
USD15, 1h

2:00pm

Museum of Science and Industry

Spend the afternoon exploring this vast interactive museum, open daily 9:30am - 4pm except Tuesdays.
USD25, 3h

5:30pm

Walk through Jackson Park and Wooded Island

Relax around scenic lagoons and gardens nearby the Museum.
Free, 1h

7:00pm

Dinner at The Promontory

Dine with live music or enjoy the rooftop space serving inventive American cuisine.
USD50, 1h30m
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Day 6: Cultural & Riverwalk Day

Chicago, USA on July 17, 2025

8:00am

Breakfast at Do-Rite Donuts & Chicken

Try Chicago’s favourite donuts paired with fresh coffee, open from 7am.
USD12, 1h

9:30am

Visit the Museum of Contemporary Art Chicago

Experience cutting-edge contemporary exhibits; open 10am-5pm, closed Mondays.
USD15, 2h

12:00pm

Lunch at Cindy's Rooftop

Enjoy stylish rooftop dining with views of Millennium Park and Lake Michigan.
USD35, 1h

2:00pm

Stroll Chicago Riverwalk

Walk along the scenic riverwalk with shops, bars, and boat rentals; open all day.
Free, 2h

5:00pm

Visit Willis Tower Skydeck

Take in panoramic views from the 103rd floor, open until 10pm. Try the glass ledge for thrills.
USD30, 1h

7:30pm

Dinner at RPM Italian

Savour upscale Italian dishes in a sleek setting near downtown.
USD60, 1h30m
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Day 7: Shopping and Departure

Chicago, USA on July 18, 2025

8:00am

Breakfast at Doughnut Vault

Grab gourmet doughnuts to start your last day in Chicago; opens at 8am.
USD10, 30m

9:00am

Shop along the Magnificent Mile

Explore luxury boutiques and famed department stores on this iconic Chicago shopping street.
Free to browse, 3h

12:30pm

Lunch at The Gage

Enjoy upscale gastropub fare across from Millennium Park before departing the city.
USD35, 1h

2:00pm

Prepare for departure / airport transfer

Allow sufficient time for travel to the airport and check-in procedures.
USD40, Varies
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