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Family-Friendly Chicago Itinerary with L Train Travel: May 9-12, 2025

Viewed by 75 travelers

Day 1: Hotel Arrival & Leisure

Chicago, USA on May 9, 2025

1:00pm

Check-in & Settle at Hyatt Regency O'Hare

Arrive and get comfortable at the hotel with the family.
Included, 30m

1:30pm

Relax and Enjoy Hotel Amenities

Spend the afternoon relaxing at the hotel or exploring nearby amenities perfect for kids and parents.
Free, 2h30m
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Day 2: Navy Pier & Grant Park

Chicago, USA on May 10, 2025

8:00am

Breakfast at Yolk near Hyatt

Hearty breakfast with kid-friendly options to start the day well.
USD15 per person, 1h

9:00am

Leisure Morning Near Hotel

Enjoy some quiet morning time or hotel activities before heading out.
Free, 8h30m

5:30pm

L Train Blue Line to Washington Station then Uber to Navy Pier

Take the Blue Line train to downtown Chicago and Uber the last part to Navy Pier for an evening excursion.
USD5 per person for train + USD15 Uber, 1h15m

6:45pm

Dinner at Riva Crabhouse, Navy Pier

Enjoy seafood and lakeside views with family-friendly menu options.
USD25 per person, 1h30m

8:15pm

Centennial Wheel Ride at Navy Pier

Experience breathtaking city and lake views on the iconic Ferris wheel at sunset.
USD16 adult, USD10 child, 45m

9:00pm

Uber to Buckingham Fountain

Short Uber ride to enjoy the illuminated evening water show at the fountain.
USD15, 30m

9:30pm

L Train Blue Line back to O'Hare

Return to the hotel by Blue Line train after a fun evening out.
USD5 per person, 50m
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Day 3: Grant Park & Lincoln Park

Chicago, USA on May 11, 2025

12:00pm

L Train Blue Line to Jackson Station

Travel from O'Hare to Jackson for Grant Park, approximately 50 minutes by Blue Line.
USD5 per person, 50m

12:50pm

Explore Grant Park

Enjoy the expansive gardens, iconic fountains, and art exhibits for a relaxing outdoor family walk.
Free, 1h30m

2:20pm

Lunch at Giordano's Deep Dish Pizza

Savor Chicago’s famous deep dish pizza, a family favorite close to Grant Park.
USD25 per person, 1h

3:30pm

L Train Blue Line to Fullerton Station

Continue by Blue Line to Fullerton Station for a visit to Lincoln Park (about 20 minutes).
USD5 per person, 20m

4:00pm

Visit Lincoln Park Zoo and Park

Explore the free Lincoln Park Zoo and surrounding green spaces, perfect for the kids to enjoy animals and playgrounds.
Free, 1h30m

5:30pm

Dinner at Café Ba-Ba-Reeba!

Enjoy a Spanish tapas dinner with family-friendly options, just a short walk from the zoo.
USD25 per person, 1h

6:45pm

L Train Blue Line back to O’Hare

Return to the hotel via Blue Line after a full day of exploring parks and zoo.
USD5 per person, 55m
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Day 4: River Cruise & Skydeck

Chicago, USA on May 12, 2025

9:00am

Prepare and Pack

Get ready for checkout and final adventures in downtown Chicago.
Free, 1h

10:00am

L Train Blue Line to Washington Station

Travel from O’Hare to downtown on the Blue Line to start the day.
USD5 per person, 50m

10:50am

Visit Starbucks Reserve Roastery

Enjoy unique coffee and treats in this special flagship store, interesting for adults and enjoyable for kids too.
Free entry, optional purchase, 1h30m

12:20pm

Walk to Chicago Riverwalk

Take a scenic 10-minute walk along the river to the cruise departure dock.
Free, 30m

12:50pm

Architecture River Cruise

Explore Chicago’s iconic buildings and history on this family-friendly 90-minute boat tour.
USD53 adult, USD41 child, 1h30m

2:20pm

Lunch at Beatrix Restaurant

A pleasant spot near Riverwalk offering fresh meals and kid-friendly dishes.
USD20 per person, 1h30m

3:50pm

Visit Millennium Park or Willis Tower Skydeck

If time allows, enjoy Millennium Park’s outdoor art; alternatively, book Willis Tower Skydeck earlier if preferred to experience panoramic views (last entry 4pm).
Millennium Park Free; Willis Tower USD35 adult, USD28 child, 1h

4:50pm

L Train Blue Line back to Hyatt Regency O’Hare

Return to the hotel to conclude your Chicago trip by train.
USD5 per person, 50m
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