Family-Friendly Chicago Trip: Downtown Stay, Budget Hotels & Fun Activities for Teens and Adults

Day 1: Arrival & Settling In

Chicago, IL, USA on August 9, 2025

3:00pm

Arrival at Chicago Union Station

Arrive in Chicago by train from Michigan, using Amtrak for a scenic and convenient trip avoiding driving hassles.
USD$75 per ticket estimate, 1h30m

5:00pm

Hotel Check-in - Freehand Chicago

Stay at Freehand Chicago, a boutique hostel-style hotel in River North with private rooms suitable for families and groups, known for its stylish decor. The total for six people for 4 nights should be around $2,100, comfortably under budget.
USD$2100 total, 0h30m

7:00pm

Dinner at The Little Beet Table

Affordable and aesthetic healthy restaurant located near the hotel offering vibrant, fresh meals perfect for all ages.
USD$20-30 per person, 1h
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Day 2: Parks & Museums

Downtown Chicago, IL, USA on August 10, 2025

8:30am

Breakfast at Yolk - Downtown

A popular spot offering hearty, affordable breakfast options including pancakes and omelets, good for fueling up before a big day.
USD$10-15 per person, 1h

10:00am

Millennium Park Visit

Explore Chicago's iconic Millennium Park to see Cloud Gate ('The Bean'), Crown Fountain, and beautiful outdoor gardens.
Free, 2h

12:30pm

Lunch at Giordano’s

Try Chicago style deep-dish pizza at Giordano’s, a family-friendly and affordable spot loved by locals and visitors.
USD$15-20 per person, 1h

2:00pm

Museum Campus: Field Museum or Shedd Aquarium

Visit one of these famous and interactive museums that's great for teens and adults. Both open around 9:00am to 5:00pm.
USD$30 per adult, USD$20 teen, 3h

6:00pm

Dinner at Portillo's Hot Dogs

A Chicago staple with affordable prices. Offers classic Chicago hot dogs and Italian beef sandwiches.
USD$10-15 per person, 1h
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Day 3: Navy Pier & Shopping

Downtown Chicago, IL, USA on August 11, 2025

8:00am

Breakfast at Wildberry Pancakes & Cafe

Highly rated place for affordable and aesthetic breakfast with pancakes and fresh berries, close to the Pier.
USD$15-20 per person, 1h

9:30am

Navy Pier Exploration

Walk around Navy Pier with rides, shops, and stunning lake views. Take the Centennial Wheel for panoramic city views.
Ride $18 per person, walking free, 3h

1:00pm

Lunch at Riva Crabhouse (at Navy Pier)

Casual, affordable seafood with a view of Lake Michigan and a menu fit for family dining.
USD$15-25 per person, 1h

2:30pm

Magnificent Mile Shopping

Explore this famous shopping district along Michigan Avenue for affordable souvenirs, clothes, and aesthetic boutiques.
Variable depending on shopping, 3h

6:30pm

Dinner at Eataly Chicago

Italian marketplace restaurant with multiple inexpensive options such as pizza and pasta, plus an inviting atmosphere.
USD$15-25 per person, 1h
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Day 4: Lincoln Park & Zoo

Lincoln Park, Chicago, IL, USA on August 12, 2025

8:30am

Breakfast at Cafe Ba-Ba-Reeba!

Spanish tapas breakfast spot with affordable and unique breakfast options, great for starting the day full of energy.
USD$10-15 per person, 1h

10:00am

Lincoln Park Zoo Visit

Free admission zoo featuring a wide variety of animals; perfect for all ages and an enjoyable, relaxing experience.
Free, 2h

12:30pm

Lunch at Chicago Pizza and Oven Grinder Co.

Affordable, cozy eatery with Chicago-style pot pies and pizzas popular with families.
USD$15-20 per person, 1h

2:00pm

Walk in Lincoln Park Neighborhood

Explore local shops, bakeries, and cafes with charming aesthetic, avoiding tourist crowds and enjoying a genuine city vibe.
Free, 2h

6:00pm

Dinner at Big Star Wicker Park

Casual taco spot with good vibes and affordable prices, includes outdoor seating that's kid-friendly.
USD$10-15 per person, 1h
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Day 5: Departure Day

Chicago, IL, USA on August 13, 2025

8:00am

Breakfast at Hotel or nearby cafe

Enjoy a leisurely breakfast nearby to pack up and prepare for departure.
USD$10-15 per person, 1h

10:00am

Check-out and walk to Union Station

Leave hotel and head to Union Station for train ride back to Michigan.
Included in ticket, 0h30m
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