Budget-Friendly Chicago Road Trip Itinerary

Day 1: Explore Chicago

Chicago, IL

8:00AM

Breakfast at Lou Mitchell's

Start your day with a hearty breakfast at Lou Mitchell's, a classic diner famous for its pancakes and free milk duds.
Located at 565 W Jackson Blvd, a central spot to kick off your Chicago adventures.
USD15, 1 hour

9:30AM

Visit Millennium Park

Stroll through Millennium Park and enjoy the iconic Cloud Gate sculpture, also known as 'The Bean'.
From Lou Mitchell’s, it's just a 10-minute walk or a short bus ride.
Free, 1.5 hours

11:00AM

Explore the Art Institute of Chicago

Visit the renowned Art Institute of Chicago, housing thousands of artworks, including pieces by Monet and Van Gogh.
Approximately a 15-minute walk from Millennium Park.
USD25, 2 hours

1:30PM

Lunch at Portillo's

Enjoy a classic Chicago-style hot dog or an Italian beef sandwich for lunch at Portillo's.
Around a 15-minute walk from the Art Institute.
USD10, 1 hour

2:30PM

Walk Along The Chicago Riverwalk

Take a leisurely stroll along the Chicago Riverwalk, appreciating the city's architecture and vibrant atmosphere.
Located just a few blocks from Portillo's, you can easily walk there.
Free, 1.5 hours

4:00PM

Visit Navy Pier

Spend the afternoon at Navy Pier, exploring shops, parks, and the beautiful views over Lake Michigan.
Take the bus or walk along the Riverwalk to Navy Pier, about a 20-minute stroll.
Free, 2 hours

6:30PM

Dinner at Giordano's

Savor a Chicago deep-dish pizza for dinner at Giordano's, a local favorite.
A 10-minute bus ride from Navy Pier takes you to Giordano's.
USD20, 1.5 hours

8:00PM

Settle into Hotel in Naperville

Head back to Naperville for the night and check into your budget hotel, ready for another day of exploring.
Drive back via I-88 W, it takes about 40 minutes.
USD120 (for the night), 1 hour
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Day 2: Discover Naperville

Naperville, IL

8:00AM

Breakfast at Egg Harbor Café

Start your morning with a delightful breakfast at Egg Harbor Café, known for its fresh ingredients and inviting atmosphere.
Located at 116 S Washington St, easily accessible from your hotel.
USD12, 1 hour

9:30AM

Explore the Riverwalk

Wander along Naperville Riverwalk, enjoying scenic views, fountains, and charming shops.
Only a short drive or a pleasant walk from the café.
Free, 1.5 hours

11:00AM

Visit Naperville Riverwalk and Moser Tower

Climb to the top of Moser Tower for panoramic views of the area and photograph the beautiful surroundings.
A quick walk from the Riverwalk.
USD5, 1 hour

12:30PM

Lunch at Lou Malnati's Pizzeria

Enjoy a local favorite for lunch at Lou Malnati's, where you can taste the delicious Chicago-style deep-dish pizza.
Walk or drive to the nearby location, around a 5-minute drive.
USD15, 1.5 hours

2:00PM

Visit Naper Settlement

Explore Naper Settlement, an outdoor history museum that showcases Naperville's rich heritage.
Located a short distance from Lou Malnati's, you can drive there in under 10 minutes.
USD10, 2 hours

4:30PM

Relax at Centennial Beach

Spend the afternoon relaxing at Centennial Beach, a beach area with a large swimming area and sandy shore.
A quick drive from Naper Settlement, around 5 minutes.
USD8, 2 hours

6:30PM

Dinner at The Lantern

Enjoy a cozy dinner at The Lantern, known for its relaxed atmosphere and delicious American fare.
Located downtown Naperville, about a 10-minute drive from the beach.
USD20, 1.5 hours

8:00PM

Head Home

Conclude your quick getaway back to your starting location, having created some great memories.
Make your way home via I-88 W, a straightforward 30-minute drive.
Free, 1 hour
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