Chicago, IL: A Local’s 3-Day Guide To America’s Best Big City!
As locals of Chicago, we absolutely love our city and know it well. From iconic attractions to hidden gems, Chicago has something for everyone. Chicago’s food scene is spectacular and we love eating our way around the city. This guide gives some of our best recs for your next trip! Here’s our recommended 3-day itinerary to explore the best of the Windy City.
Stay: Airbnb in Avondale
We recommend staying in Avondale, a neighborhood known for its residential charm, safety, and convenience. Avondale is centrally located, making it easy to access both the bustling downtown and quieter neighborhoods. Plus, you’ll find an array of great local dining options and cozy cafes nearby.
Day 1: Exploring Downtown and Classic Chicago Spots
Morning
Start your day with brunch at Café Robey, located in Wicker Park. This trendy spot offers a delicious menu with modern twists on classic dishes. The rooftop provides a perfect view of the city skyline to kick off your Chicago adventure.
Midday
After brunch, head downtown to Grant Park to see one of Chicago’s most famous landmarks, The Bean (Cloud Gate). Stroll around the park, take in the vibrant city energy, and snap some photos by this reflective sculpture.
Local Tip: Across the street from the bean you’ll find the Chicago Athletic Club, a beautifully restored building that offers various fun games like bocce, billiards, and bowling for free! The vintage feel of the club adds an old-school charm that makes it a fun, leisurely stop.
Evening
After some relaxation back at your Airbnb in Avondale, get ready for dinner at Coda Di Volpe, located in the Lake View neighborhood. Known for its wood-fired pizzas and Italian dishes, it’s a great spot to enjoy a high quality Italian meal in one of Chicago’s charming neighborhoods.
Day 2: Nature, Food, and Cocktails Across Neighborhoods
Morning
Begin your second day at the Lincoln Park Zoo, one of the oldest and most beautiful zoos in the country. Located right in Lincoln Park, the zoo is free to enter and surrounded by lovely park grounds where you can take a scenic walk along the waterfront or enjoy the gardens.
Midday
For lunch, grab a casual bite at Devil Dawgs, famous for their delicious hot dogs and burgers. This is a great spot to try the infamous Chicago Dog! Don’t forget to try one of their creamy milkshakes—they’re a local favorite.
After lunch, stop by Good Ambler in West Loop, a trendy coffee shop known for its cozy industrial atmosphere. It’s the perfect place to relax before diving back into the day.
Evening
For dinner, head to Aba in Fulton Market (highly suggest making a reservation in advance), a Mediterranean-inspired restaurant with a stunning rooftop patio. This area of the city is known for its trendy, upscale restaurants and lively atmosphere.
End the evening with cocktails at Meadowlark in Logan Square (reservations also required), a neighborhood known for its artistic vibe, hipster bars, and live music venues. Meadowlark offers creative cocktails in a relaxed setting, perfect for winding down after a day of exploring.
Day 3: Lakeside Adventures and Chinatown Delights
Morning
Start the morning with a bike ride along Lakeshore Drive, a scenic route that runs along Lake Michigan, offering incredible views of the city skyline. Your ride will take you to the Adler Planetarium, where you can stop to enjoy our favorite view of Chicago.
Midday
No trip to Chicago is complete without trying deep-dish pizza. For lunch, visit Lou Malnati’s Pizzeria, a Chicago institution known for its buttery crust and hearty deep-dish pies. This is a must-try for pizza lovers.
Afterward, catch the Chicago Water Taxi for a scenic ride down the Chicago River, and make your way to Chinatown. The taxi ride is not only convenient but offers fantastic views of the city’s iconic architecture from the water while only costing $10. If you’re willing to spend a little more you can book the architectural river tour where a tour guide will give details about the city’s amazing history.
Once in Chinatown, grab a refreshing boba tea at Daboba, a well-loved spot known for its delicious milk tea. Spend some time exploring the area’s shops and sights before dinner.
Evening
Wrap up your trip with dinner at MCCB (Modern Chinese Cook Book), where you can enjoy authentic Sichuan cuisine. This Michelin Star Chinese restaurant offers a range of mouthwatering dishes, from hot pot to stir-fried specialties. It’s the perfect way to end your Chicago adventure.
Conclusion:
Chicago is a city with endless things to see, eat, and explore. We love living in the city and eating our way around all the neighborhood. Whether you’re biking along the lakefront, sipping cocktails in Logan Square, or tasting the diverse cuisine of Chinatown, there’s always something new to discover. Enjoy your stay!
