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5-Day Shoestring Budget Itinerary for Chicago

Viewed by 104 travelers

Day 1: Arrival & Exploration

Chicago, USA

8:00AM

Breakfast at Lou Mitchell's

Start your day with a classic Chicago breakfast at Lou Mitchell's, known for their homemade doughnuts and hearty omelets, a tradition since 1923.
Located in the West Loop, an easy 10-minute walk from most downtown hotels.
USD 15, 1 hour

9:30AM

Visit Millennium Park

Wander through Millennium Park, where you can snap photos with the iconic Cloud Gate and enjoy the beautiful gardens.
A 15-minute walk from Lou Mitchell's.
Free, 2 hours

12:00PM

Lunch at Portillo's

Savor a famous Chicago-style hot dog or Italian beef sandwich at Portillo's, a local favorite.
Take the 'L' from Washington/Wells to the State/Lake Station (10 minutes).
USD 10, 1 hour

1:30PM

Explore The Art Institute of Chicago

Spend your afternoon at The Art Institute of Chicago, where you can find masterpieces from Van Gogh to Grant Wood.
A 10-minute walk from Portillo's.
USD 25, 2 hours

4:00PM

Walk along the Chicago Riverwalk

Enjoy a leisurely stroll along the picturesque Chicago Riverwalk, perfect for relaxing and taking in the skyline views.
10-minute walk along East Monroe Street.
Free, 1 hour

6:00PM

Dinner at Giordano's

Finish off your day with a classic Chicago deep-dish pizza at Giordano's, famous for its stuffed crust.
Take the 'L' from State/Lake back to Washington/Wells (10 minutes).
USD 20, 1.5 hours
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Day 2: Culture & Nature

Chicago, USA

8:00AM

Breakfast at Yolk

Fuel up with a hearty breakfast at Yolk, where the pancakes and scrambles never disappoint.
A 15-minute walk from your hotel.
USD 12, 1 hour

9:30AM

Visit Lincoln Park Zoo

Explore the Lincoln Park Zoo, one of the oldest zoos in the U.S., and it's free to enter!
Take the #151 bus from State/Lake to Lincoln Park Zoo (20 minutes).
Free, 2.5 hours

12:00PM

Lunch at The Chicago Diner

Enjoy a vegetarian lunch at The Chicago Diner, famous for their vegan milkshakes and delicious sandwiches.
A short 10-minute walk from Lincoln Park Zoo.
USD 15, 1 hour

1:30PM

Stroll through Lincoln Park

Take a walk through Lincoln Park, visiting the conservatory and relaxing by the lagoons.
The park is adjacent to the zoo.
Free, 2 hours

3:30PM

Chicago History Museum

Learn about the rich history of Chicago at the Chicago History Museum, featuring engaging exhibits.
A 10-minute walk from Lincoln Park.
USD 15, 1.5 hours

5:00PM

Dinner at R.J. Grunts

Refuel with a casual dinner at R.J. Grunts, known for its fun atmosphere and unique burgers.
On the same street as the museum.
USD 15, 1 hour
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Day 3: Architectural Wonders

Chicago, USA

8:00AM

Breakfast at Flat Iron Coffee

Start with a cozy breakfast at Flat Iron Coffee, enjoying their freshly brewed coffee and pastries.
Located downtown, a short 15-minute walk.
USD 8, 1 hour

9:30AM

Architecture River Cruise

Join an affordable architecture river cruise to learn about Chicago’s iconic buildings from the water.
Catch the cruise from the Riverwalk area.
USD 20, 1.5 hours

11:00AM

Explore Navy Pier

Stroll around Navy Pier, where you can enjoy public art installations and scenic views of Lake Michigan.
A short 10-minute walk from the Riverwalk dock.
Free, 2 hours

1:00PM

Lunch at Shake Shack

Grab a quick bite at Shake Shack for fast-casual burgers in a fun atmosphere.
Located at Navy Pier.
USD 12, 1 hour

2:30PM

Visit Shedd Aquarium

Explore the vast marine life displays at Shedd Aquarium, one of the largest aquariums in the world.
Take a scenic walk along the lakefront from Navy Pier (20 minutes).
USD 39, 2 hours

5:00PM

Dinner at The Chopping Block

Enjoy a cooking class dinner at The Chopping Block, where budget cooking meets delicious results.
Take a bus or walk back to downtown area (15 minutes).
USD 25, 2 hours
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Day 4: Shopping & Culture

Chicago, USA

8:00AM

Breakfast at Intelligentsia Coffee

Enjoy a cup of artisanal coffee and a light pastry at Intelligentsia, a local favorite.
A 15-minute walk from your hotel.
USD 10, 1 hour

9:30AM

Shopping on Magnificent Mile

Shop or window shop along the Magnificent Mile, boasting a variety of popular stores and boutiques.
Easily accessible by foot from downtown.
Free, 2 hours

12:00PM

Lunch at a Food Truck

Try out a local food truck for a quick and budget-friendly lunch experience.
Various food trucks located around the Magnificent Mile.
USD 10, 1 hour

1:30PM

Visit the Museum of Contemporary Art

Explore innovative exhibits at the Museum of Contemporary Art, featuring work from modern artists.
A 10-minute walk from your lunch stop.
USD 15, 1.5 hours

3:00PM

Self-Walk Art Tour in Streeterville

Take a self-guided art tour in the Streeterville neighborhood, spotting unique public art pieces.
Begin at the MCA and wander through the area.
Free, 2 hours

5:00PM

Dinner at Lou Malnati's

Indulge in more deep-dish pizza at Lou Malnati's, known for their buttery crust and South Side tradition.
Take the bus from Streeterville back to downtown (15 minutes).
USD 20, 1.5 hours
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Day 5: Final Day in Chicago

Chicago, USA

8:00AM

Breakfast at The Bongo Room

Enjoy a delicious breakfast with creative twists at The Bongo Room – their French Toast is a must-try.
A 20-minute walk from downtown.
USD 15, 1 hour

9:30AM

Visit the Field Museum

Explore the Field Museum of Natural History, home to fascinating exhibits including the famous T-Rex Sue.
Take the bus from downtown (20 minutes).
USD 36, 2.5 hours

12:00PM

Lunch at The Art Institute's Café

Enjoy light, fresh options for lunch at the café within The Art Institute before continuing your day.
A 10-minute walk from the Field Museum back to the museum.
USD 12, 1 hour

1:30PM

Visit Grant Park

Spend some time in Grant Park, enjoying the open spaces and gardens. Consider taking a few pictures at the Crown Fountain.
A 10-minute walk from The Art Institute.
Free, 1 hour

3:00PM

Wrap-up at Navy Pier

Return to Navy Pier for a final stroll, looking for any last-minute souvenirs or simply enjoying the atmosphere.
Take the bus from downtown to Navy Pier (20 minutes).
Free, 2 hours

5:00PM

Dinner at Pequod's Pizza

End your trip with some more delicious Chicago-style pizza at Pequod's – the caramelized crust is to die for!
Take the bus back to Lincoln Park area (30 minutes).
USD 20, 1.5 hours
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