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Two-Week Chicago Itinerary: Exploring the Windy City's Best in May

Viewed by 135 travelers

Day 1: Downtown Landmarks

Chicago, USA on May 1, 2025

8:00am

Breakfast at Wildberry Pancakes and Cafe

Start your day with hearty pancakes or omelets at this popular downtown spot, open from 7am to 3pm, perfect for fueling a day of sightseeing.
USD20, 1h

9:30am

Millennium Park

Visit the iconic Cloud Gate sculpture (aka 'The Bean') and stroll the beautiful gardens and fountains. The park is open daily from 6am to 11pm and offers terrific photo opportunities.
Free, 1h30m

11:00am

Art Institute of Chicago

Explore world-class art collections including Impressionist and American masterpieces. Open 10:30am to 5pm on weekdays, tickets cost around USD25.
USD25, 2h

1:30pm

Lunch at The Gage

Enjoy upscale American pub fare with a view of Millennium Park, open 11:30am to 11pm daily.
USD30, 1h

3:00pm

Chicago Architecture River Cruise

Take a 90-minute river cruise to learn about Chicago's famous skyscrapers and history. Cruises run from 9am to 6pm with tickets around USD50.
USD50, 1h30m

6:00pm

Dinner at Girl & The Goat

Dine at one of Chicago’s hottest restaurants, known for creative shared plates. Reservations recommended. Open 4pm to 10pm.
USD60, 2h
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Day 2: Lincoln Park & Zoo

Chicago, USA on May 2, 2025

8:30am

Breakfast at Toast

Enjoy a classic American breakfast with generous portions in Lincoln Park; open 7am to 3pm.
USD18, 1h

10:00am

Lincoln Park Zoo

Visit one of the oldest free zoos in the country, showcasing a wide variety of animals. Open 10am to 5pm daily, free admission.
Free, 2h

12:30pm

Lunch at Café Ba-Ba-Reeba!

Relax with Spanish tapas in the neighborhood, open from noon to 10pm.
USD25, 1h

2:00pm

Walk through Lincoln Park Conservatory

Explore exotic plants in this historic glass greenhouse, open 9am to 5pm, free entry.
Free, 1h

3:30pm

North Avenue Beach

Head over to the lakefront beach for a relaxing afternoon stroll or people-watching. The beach is open all day in May.
Free, 2h

6:00pm

Dinner at Alinea (reservation needed)

Experience innovative fine dining at this Michelin 3-star restaurant, open Tuesdays through Saturdays. Book well in advance. Dinner typically around USD250 per person.
USD250, 3h
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Day 3: Museum Campus

Chicago, USA on May 3, 2025

8:00am

Breakfast at Yolk

Try creative breakfast dishes near the Museum Campus, open 7am to 2pm.
USD20, 1h

9:30am

Shedd Aquarium

Explore one of the largest indoor aquariums in the world. Open 9am to 5pm daily, adult admission around USD40.
USD40, 3h

1:00pm

Lunch at Museum Campus Café

Grab a quick bite at the on-site café inside the Museum Campus area, open 10am to 4pm.
USD15, 1h

2:15pm

Field Museum of Natural History

Discover extensive natural history exhibits including the famous T-Rex 'Sue'. Open 9am to 5pm, tickets about USD40.
USD40, 3h

6:00pm

Dinner at The Signature Room at the 95th

Enjoy fine dining with panoramic city views from the John Hancock Center, open daily from 4:30pm.
USD50, 2h
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Day 4: Frank Lloyd Wright Tour

Oak Park, USA on May 4, 2025

8:00am

Breakfast at The Bongo Room

Before heading to Oak Park, enjoy creative breakfast options downtown, open 7am to 2pm.
USD22, 1h

9:30am

Travel to Oak Park

Short 20-minute drive west of Chicago city center.
USD10 (taxi or public transit), 30m

10:00am

Frank Lloyd Wright Home and Studio

Tour the house and studio of the famous architect. Open 10:30am to 4:30pm with guided tours recommended, tickets USD20.
USD20, 1h30m

12:00pm

Lunch at Split Rail

Enjoy contemporary American cuisine in an artsy setting nearby. Open noon to 9pm.
USD30, 1h

1:30pm

Oak Park River Forest Museum

Learn more about the local history and cultural heritage, open 1pm to 4pm, donation suggested.
Suggested donation USD5, 1h

3:00pm

Wander Oak Park Neighborhood

Explore charming streets and shops known for arts, crafts, and local boutiques.
Free, 2h

5:30pm

Return to Chicago

Make your way back to central Chicago for dinner.
USD10, 30m

7:00pm

Dinner at Smoque BBQ

Relax with some of Chicago's best barbecue, open until 9pm.
USD35, 1.5h
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Day 5: Hyde Park & University

Chicago, USA on May 5, 2025

8:30am

Breakfast at Valois

Start the day in Hyde Park with a no-frills diner breakfast favorite, open 7am to 3pm.
USD10, 1h

10:00am

University of Chicago Campus Tour

Walk the historic Gothic architecture and beautiful grounds. Self-guided tours are flexible throughout the day, free.
Free, 1h30m

11:45am

Museum of Science and Industry

Explore one of the largest science museums in the world, open daily 9:30am to 4pm, tickets about USD25.
USD25, 3h

3:00pm

Relax at Jackson Park

Enjoy this peaceful urban park with lake views, open daylight hours.
Free, 1h30m

5:00pm

Dinner at Promontory

Contemporary American cuisine with a great atmosphere in Hyde Park, open till 10pm.
USD40, 2h
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