Chicago Foodie Adventure: 4-Day City Itinerary

Day 1: Culinary Kickoff

Chicago, IL

8:00 AM

Breakfast at Wildberry Pancakes & Cafe

Start your Chicago journey with the renowned Wildberry Pancakes, known for their berry bliss pancakes and creative flavors.
Head east on Wacker Dr towards N Michigan Ave.
USD20, 1.5 hours

10:00 AM

Chicago Riverwalk

Take a stroll along the scenic Riverwalk, enjoying the views of the spectacular city skyline and vibrant public art.
Walk west along E Wacker Dr.
Free, 1.5 hours

12:00 PM

Lunch at Portillo's

Dive into Chicago's classic deep-dish experience with Portillo's famous Italian beef sandwich and loaded fries.
Catch the 'L' train at State/Lake station to Washington/Wells.
USD15, 1.5 hours

2:00 PM

Visit the Art Institute of Chicago

Explore impressive collections of Impressionist works, modern art, and architecture at one of the most visited art museums in the world.
Walk from Portillo's to the Art Institute, located at S Michigan Ave.
USD25, 2 hours

4:30 PM

Chicago Food Tour

Embark on a guided food tour to sample local delicacies from pizza and hot dogs to desserts in various neighborhoods.
Meet your tour at the Art Institute.
USD75, 3 hours

8:00 PM

Dinner at Girl & The Goat

Savor globally inspired dishes at this critically acclaimed restaurant, known for its emphasis on shared plates and local ingredients.
Walk or take a quick rideshare to West Loop.
USD60, 2 hours
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Day 2: Cultural Exploration

Chicago, IL

9:00 AM

Breakfast at Yolk

Indulge in a delicious breakfast at Yolk, famous for their creative omelets and fresh juices.
Walk or take a short rideshare to the Yolk location.
USD18, 1.5 hours

10:30 AM

Museum of Science and Industry

Discover interactive exhibits showcasing Chicago's history in innovation and scientific discovery.
Take the Green Line train to 55th/Cento.
USD22, 2.5 hours

1:00 PM

Lunch at The Promontory

Unwind with a hearty lunch featuring a mix of American dishes and craft cocktails at this neighborhood gem.
Walk to the Promontory, located in Hyde Park.
USD30, 1.5 hours

3:00 PM

Visit the Field Museum

Marvel at the impressive exhibits at the Field Museum, home to Sue the T. rex and ancient artifacts.
Take a bus or rideshare to the Field Museum.
USD28, 2.5 hours

6:00 PM

Dinner at Lou Malnati's

Experience the iconic Chicago deep-dish pizza at Lou Malnati's, a must-try for any guest.
Take a rideshare back downtown.
USD25, 1.5 hours

8:00 PM

Skydeck Chicago

End your day by catching stunning panoramic views of the city from the Skydeck on the 103rd floor of Willis Tower.
Walk to the Skydeck at 233 S. Wacker Dr.
USD30, 1 hour
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Day 3: Neighborhood Nibbles

Chicago, IL

9:00 AM

Breakfast at Little Goat Diner

Start your day with a creative twist on classic diner food, including delicious sandwiches and pancakes.
Walk to the Little Goat Diner in West Loop.
USD20, 1.5 hours

11:00 AM

Explore Lincoln Park

Wander through Lincoln Park, visiting the conservatory and zoo while enjoying nature in the city.
Take the 'L' train northbound to Fullerton.
Free, 2 hours

1:00 PM

Lunch at The Chicago Diner

Savor a classic vegetarian meal at the Chicago Diner, famous for its Vegan ‘Junk Food’ and milkshakes.
Ride a rideshare to the Diner.
USD25, 1.5 hours

3:00 PM

Visit the Museum of Contemporary Art

Explore thought-provoking exhibitions at the Museum of Contemporary Art, showcasing innovation and creativity.
Take a bus to the museum.
USD15, 2 hours

5:30 PM

Dinner at RPM Italian

Delight in modern Italian cuisine at RPM Italian, where the stylish ambiance enhances your dining experience.
Take a ride back to the River North neighborhood.
USD55, 2 hours

8:00 PM

Live Jazz at The Green Mill

Enjoy live music at The Green Mill Cocktail Lounge, an iconic jazz club that exudes vintage charm.
Take a rideshare to The Green Mill.
USD20, 2 hours
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Day 4: Final Food Frenzy

Chicago, IL

9:00 AM

Breakfast at The Bongo Room

Indulge in their famous chocolate caramel gooey cake pancakes to kickstart your last day.
Walk to The Bongo Room in Wicker Park.
USD18, 1.5 hours

10:30 AM

Explore Wicker Park

Take a leisurely walk around Wicker Park, visiting unique shops, and enjoying street art.
Stroll around the area.
Free, 1.5 hours

12:00 PM

Lunch at Parlor Pizza Bar

Satisfy your cravings with gourmet pizzas and a fantastic beer selection at Parlor Pizza Bar.
Catch a bus to Parlor Pizza Bar.
USD25, 1.5 hours

2:00 PM

Visit the Chicago History Museum

Learn about Chicago's rich history through interactive exhibits and artifacts at the Chicago History Museum.
Take a rideshare to the museum.
USD20, 2 hours

5:00 PM

Dinner at The Aviary

Conclude your Chicago adventure with an unforgettable culinary experience that includes intriguing cocktails and creative dishes.
Take a rideshare to The Aviary in the Near North Side.
USD150, 2.5 hours

8:00 PM

Nightcap at The Aviary Rooftop

Enjoy a nightcap on The Aviary Rooftop, soaking in the skyline views as your adventure comes to an end.
Remain at The Aviary Rooftop.
USD20, 1.5 hours
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