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My ultimate Chicago list 🎡🛥️🏙️
17
items I’m gathering all my favorite spots to eat, sip, and explore in the Windy City — from delicious bites to fun activities. 🌭🎡✨🪁
Sections
5
Outdoor Activities
Local Favorites
Arts & Entertainment
Restaurants
Other Food & Drinks
Outdoor Activities
This boat tour will be the highlight of your trip to Windy City. Easy access from the Riverwalk, once you board, go upstairs on the open deck to have a 360-degree view of the skylines. The guides brilliantly weave in stories about iconic architectura...
CAC River Cruise aboard First Lady
What is the best way to explore the city other than walking? Agree, nothing. Riverwalk is one of the ways to see beautiful architectural buildings while enjoying the fresh air. Don’t forget to take pictures and videos for memories. There are cafes, r...
Chicago Riverwalk
Google says its name is “Cloud Gate”, but everyone calls it The Bean.
Cloud Gate
Navy Pier is Chicago’s iconic lakeside destination, offering stunning views of Lake Michigan, fun rides, shops, restaurants, and cultural attractions. Perfect for a stroll, a sunset, or a day full of family fun and photo ops. 🎡✨
Navy Pier
Local Favorites
Hands down to the best jazz lounge in town. The ambiance is top-notch, the interior and vintage decor make you feel like you've stepped into another era. Live music happens every week; make sure to check their website for the program. Ideal for impre...
The Green Mill
Truly a legendary blues club in Chicago established in 1968. Features live blues music on 2 stages, with different bands playing in each room so the music doesn’t stop. It’s typically open Thu through Sat. Cover charge is around $15-20.
Kingston Mines
Arts & Entertainment
One of the best cultural stops in Chicago. The collection is incredible—from Monet and Van Gogh to modern design. It’s very visitor-friendly. The location is central, accessible by public transit, and they offer helpful tips like booking tickets in a...
The Art Institute of Chicago
You’ll lose track of time at this museum — such a fun and interactive place to spend a few hours and get captivated by its magic. ✨
Museum of Illusions Chicago
Restaurants
I kid you not when I say that Bonci pizzeria took me back to the time when I lived in Rome. The crust here is something special - airy yet crispy. Go there if you want a fresh, creatively topped pizza in Chicago. And have an arancini for me, please.
Bonci Pizzeria
This classic cocktail bar is right in the heart of River North. The bar offers high-quality cocktails as well as food. Still thinking about the wagyu beef dip which was tender and packed with flavor. Oh btw you won’t want to miss their special chocol...
Gus' Sip & Dip
Cheese pull level: Giordano’s. The ultimate deep-dish experience! 🍕
P.S. Wait time for pizza is 45 min. Def worth the wait.
Giordano's
Other Food & Drinks
I love me a good chunky cookie. There are not only cookies, but also other baked goods like brioche, bread, muffins, and scones. My personal favorites are chocolate walnut which is the OG, and dark chocolate peanut butter cookies. Now they have opene...
Levain Bakery
Iconic spot for a quick stop after a long walk on the Riverwalk to enjoy the cocktails or wine, and bites.
Tiny Tapp & Tiny Café
Looking for a trendy spot without being try-hard, loud in a good way, and totally perfect for a fun night out with friends? Then this is the place for you. The darts game is next-level: little pods, big screens, and the kind of scoring system that tu...
Flight Club Chicago
Cindy’s Rooftop Bar is a great spot to enjoy cocktails with the view of Millennium Park and The Bean. Add it to your list for your next girls’ night out.
Cindy's Rooftop
This intimate neighborhood cocktail bar has an old-timey Paris vibe. Offers craft cocktails and bites.
The Victor Bar Chicago
This cute Japanese soufflé pancake shop makes authentic pancakes located in the Loop. Early Gray Sea Salt Caramel and Takoyaki are customers’ favorites.
Hanabusa Cafe