6-Day Ultimate Chicago Road Trip Experience

Day 1: Arrival and Exploration

Chicago, IL

8:00 AM

Breakfast at Lou Mitchell's

Start your day at this iconic diner known for its brunch staples and complimentary donut holes.
Located in the West Loop, easily accessible by car.
USD 15, 1 hour

9:30 AM

Visit the Art Institute of Chicago

Explore the extensive collection featuring works from Amedeoo Modigliani to Grant Wood’s American Gothic.
Short drive from Lou Mitchell's; parking available nearby.
USD 25, 2 hours

12:00 PM

Lunch at Giordano's

Taste Chicago's famous deep-dish pizza at Giordano's, a city staple renowned for its delicious pies.
Just a short drive or walk from the Art Institute.
USD 20, 1 hour

1:30 PM

River Architecture Cruise

Enjoy a scenic boat tour that highlights Chicago's stunning skyline and historical architecture.
Board at the Riverwalk, a short drive away.
USD 40, 1.5 hours

4:00 PM

Museum of Science and Industry

Delve into engaging exhibits about science, technology, and industry in one of the largest science museums.
A 20-minute drive from the Riverwalk.
USD 22, 2.5 hours

7:00 PM

Dinner at The Chicago Diner

Enjoy delicious vegetarian comfort food and the famous Radical Reuben sandwich at this local gem.
20-minute drive from the museum.
USD 25, 1.5 hours

9:00 PM

Explore Millennium Park

Stroll through the park, enjoying its famous Cloud Gate sculpture and beautiful night lights.
Short 15-minute drive from the diner.
Free, 1 hour
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Day 2: Cultural Immersion

Chicago, IL

8:00 AM

Breakfast at Al's #1 Italian Beef

Start your day with a classic Italian beef sandwich, a must-try Chicago favorite.
Located in Little Italy; about a 10-minute drive from downtown.
USD 10, 1 hour

9:30 AM

Field Museum

Discover incredible exhibitions ranging from ancient Egypt to dinosaur fossils.
Just a short drive from the restaurant.
USD 24, 3 hours

1:00 PM

Lunch at Max's Takeout

Savor the famous Chicago-style hot dog at this beloved local eatery.
A 15-minute drive from the Field Museum.
USD 12, 1 hour

2:30 PM

Museum of Contemporary Art

Experience modern art at this inspiring museum featuring rotating exhibitions and events.
Drive 10 minutes from Max's to the museum.
USD 15, 1.5 hours

4:00 PM

Lincoln Park Zoo

Visit one of the oldest zoos in the country, free and beautifully landscaped.
About 20 minutes from the Museum of Contemporary Art.
Free, 2 hours

6:30 PM

Dinner at Ramen-san

Indulge in delicious Japanese ramen with a variety of broth and toppings in a vibrant atmosphere.
A 15-minute drive from the zoo.
USD 20, 1.5 hours

8:00 PM

Chicago Comedy Show

End your evening with laughter at a legendary comedy club in the city.
Short drive to the club (depending on which club you choose).
USD 30, 2 hours
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Day 3: Nature and Views

Chicago, IL

8:00 AM

Breakfast at Wildberry Pancakes & Cafe

Enjoy a delicious pancake breakfast or a healthy smoothie bowl in this bustling cafe.
Located downtown, park nearby.
USD 20, 1 hour

9:30 AM

Visit Chicago Botanical Garden

Take a tour of this magnificent landscape featuring diverse gardens and beautiful paths.
About a 30-minute drive from downtown.
USD 12, 2 hours

12:00 PM

Lunch at Park Grill

Dine with a view of Millennium Park and enjoy local dishes at this vibrant restaurant.
Drive back to Millennium Park, about 30 minutes.
USD 25, 1 hour

1:30 PM

Lakefront Trail Walk

Walk along Lake Michigan’s stunning path to take in the sights and fresh air.
Start at Millennium Park, right after lunch.
Free, 2 hours

4:00 PM

Observation Deck at Willis Tower

Get breathtaking views of Chicago from the 103rd floor observation deck.
A 10-minute drive away from the Lakefront Trail.
USD 30, 1 hour

6:00 PM

Dinner at The Purple Pig

Savor Mediterranean-inspired dishes and wine in a charming atmosphere.
A short drive from Willis Tower.
USD 35, 1.5 hours

8:00 PM

Nighttime Riverwalk Stroll

Take a relaxing evening stroll along the illuminated riverwalk and enjoy the views.
Drive to the starting point of the Riverwalk.
Free, 1 hour
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Day 4: Historical Insights

Chicago, IL

8:00 AM

Breakfast at Dhaba Indian Restaurant

Try delicious Indian dishes at this unique restaurant for a flavorful start to your day.
About a 20-minute drive from downtown.
USD 15, 1 hour

9:30 AM

Visit the Chicago History Museum

Discover Chicago’s rich history with interactive exhibits and artifacts.
A 10-minute drive from the restaurant.
USD 20, 2 hours

12:00 PM

Lunch at Slurp Slurp

Indulge in delicious Asian noodle soups and street-style snacks.
A quick 10-minute drive from the museum.
USD 15, 1 hour

1:30 PM

Explore Old Town

Stroll through this charming neighborhood filled with historical buildings and boutique shops.
Just a 5-minute drive from lunch.
Free, 1.5 hours

3:00 PM

Visit the International Museum of Surgical Science

Explore exhibitions about surgical history and medical tools at this unique museum.
A 15-minute drive from Old Town.
USD 15, 2 hours

5:30 PM

Dinner at The Gage

End the day with a sumptuous meal featuring seasonal ingredients in a cozy bistro.
A 20-minute drive from the museum.
USD 40, 1.5 hours

8:00 PM

Local Blues Club

Experience the vibrant blues music scene in a local club that will have you dancing.
Head to the nearby club, 10-minute drive.
USD 25, 2 hours
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Day 5: Family Fun Day

Chicago, IL

8:00 AM

Breakfast at Oak Tree Restaurant

Fuel up with a hearty breakfast and enjoy a family-friendly dining atmosphere.
Located near Lincoln Park.
USD 15, 1 hour

9:30 AM

Shedd Aquarium

Discover the wonders of aquatic life at this incredible aquarium with various exhibits.
A short drive from the restaurant.
USD 30, 2.5 hours

12:00 PM

Lunch at Harry Caray's Tavern

Enjoy American classics and view memorabilia from the famous sports commentator.
Located nearby the aquarium.
USD 25, 1 hour

1:30 PM

Navy Pier

Spend the afternoon exploring amusements, rides, and shops along the pier.
Short 10-minute drive from lunch.
Free (attractions extra), 3 hours

5:00 PM

Dinner at Bubba Gump Shrimp Co.

End the day at this fun family-themed restaurant inspired by the film Forrest Gump.
Located on Navy Pier.
USD 30, 1.5 hours

7:00 PM

Nighttime Yacht Cruise

Enjoy a relaxing evening cruise on Lake Michigan with fantastic city views.
Various departure points near Navy Pier.
USD 50, 2 hours
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Day 6: Relaxation and Departure

Chicago, IL

8:00 AM

Brunch at Beatrix

Enjoy a health-conscious menu with brunch options that cater to various dietary preferences.
Located in River North; easy to park nearby.
USD 25, 1.5 hours

10:00 AM

Visit the Chicago Planetarium

Experience spectacular cosmic shows and exhibitions at one of America’s oldest planetariums.
A short drive from Beatrix.
USD 20, 2 hours

12:30 PM

Lunch at the Smith

Savor an upscale American lunch in a contemporary setting.
Located downtown; just 15 minutes away.
USD 30, 1 hour

2:00 PM

Last-minute Shopping at Magnificent Mile

Explore the famous shopping district to find souvenirs and luxury goods.
About a 10-minute drive from the Smith.
Variable, 2.5 hours

5:00 PM

Departure

Return your rental car and prepare for your onward journey, taking unforgettable Chicago memories with you.
Drive to rental location as per final arrangements.
Variable, 1 hour
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