The question I get asked the most on Instagram is for recommendations on places to go and eat in Chicago. And it makes sense given how much I talk about my love of Chicago. So it’s high time I actually put up, or shut up! lol.
If you’re lucky enough to be visiting Chicago in the summer, you’re in for a lifechanging experience. This city is magical in the summer. But don’t worry, if you’re here braving the winter there’s still plenty of fun to get into.
Here is my list of things to do in Chicago. It includes some of my favorite activities and restaurants as well as things I haven’t tried yet but that you definitely should.
Note: I will actively update this list so check back for new recommendations.
Last updated: 8/19/24
Restaurants + Rooftops
I’ve said it once and I’ll say it with my last breath… Chicago has the best food in the country! It’s not up for debate. This is a foodie city and no matter what type of cuisine, vibe or price point you’re looking for, we’ve got the best version of it.
I won’t pretend to know every single hot spot or amazing restaurant in the city (because the list is infinite), but here are quite a few of my favorites:
Au Cheval / Small Cheval – home to the #1 ranked burger in the country
Parson’s Chicken & Fish – casual vibe with great outdoor space and games; dog friendly
RPM Seafood – outdoor space with great view of the Chicago River
Soulé – incredible soul food (Black, female owned)
14 Parish – Caribbean inspired cuisine (Black owned)
Batter & Berries – popular brunch spot; get there early! (Black owned)
Luella’s Southern Kitchen – Southern cuisine, brunch (Black 0wned)
Shore Club – outdoor casual beach side American food (summer only)
The Whale – dinner + brunch spot with outdoor seating (in summer) and great playlists
LondonHouse Rooftop – upscale summer rooftop + brunch spot
Cindy’s Rooftop – upscale rooftop with drinks, food and stunning view overlooking Millennium Park/”The Bean”
ROOF on theWit – hotel rooftop and brunch spot with day party vibes
Adorn Bar + Restaurant – upscale restaurant inside the Four Seasons hotel
Gino + Marty’s – upscale Italian restaurant + bar with live DJ (Black owned)
Three Dots and a Dash – casual speakeasy tropical/tiki themed bar
Violet Hour – hidden Prohibition style bar
Ramen San – Japanese ramen with 90’s hip-hop playlists (order the Brussels sprouts!)
Eden – upscale new American cuisine
TAO – upscale Asian bistro; also has a nightclub
Maple & Ash (patio) – upscale outdoor dining; indoor dining available
Happy Lamb Hot Pot – all you can eat casual and authentic hot pot
The Divan – supperclub with live music
Hotels
Deciding on a place to stay is always the toughest part of my travel plans. I love hotels with luxury amenities, excellent customer service and room service is a must. The thing about me is I’m a vacationer and not a traveler. I like a place that whether I’m relaxing after a day of sightseeing or decide to stay in bed all day and watch tv, I know I’m going to experience the ultimate comfort.
Here are my favorite hotels and recommendations for your Chicago stay:
The Pendry* – downtown ^ *my personal favorite and go-to
Four Seasons – downtown ^
The Langham – downtown ^
The Peninsula – downtown ^, great spa
Nobu – West Loop Fulton Market ^
Soho House – Fulton Market, members discount available
Virgin Hotel – downtown ^
^ = pet friendly
Activities
Although I love to relax on vacation, if you’ve followed along with any of my trips you know I love an itinerary that includes a little adrenaline rush. I’ve bungee jumped, sky dived, gone snowmobiling, jumped in a frozen lake, you name it. And while I won’t go just that far with my recommendations (I will if you want me to!), there are still plenty of other exciting things to do in the city.
Kayaking on the Chicago River – $65 to $85 depending on the tour
Helicopter Tour of the City – $795 for 3 passengers; multiple flight options
Boat Cruise/Party – varies
Ice skating in Millennium Park – free admission, $10 to rent skates (winter only)
Kohler Waters Spa in Lincoln Park – luxury sauna and spa
Skydeck “The Ledge” – thrill experience, $32 to $36 for adults
360 Chicago “Tilt” – thrill experience, adult tickets start at $44
Architectural Boat Tour – tickets start at $28; average cruise ~$45
Indoor Skydiving – tickets start at $89 pp
Golf the Green – indoor golf + bar, $75/hr
Rock Climbing in Maggie Daley Park – tickets start at $15
Museum of Ice Cream – general admission $33; VIP $68
The Art Institute of Chicago – general admission $32
Navy Pier Ferris Wheel – private gondola $99
Cubs or White Sox Game – varies
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I absolutely love Chicago. It’s a city so rich in culture, amazing architecture, unbelievable food and some of the nicest people you will ever meet. I will never stop bragging about this city and I’m so grateful to be able to call Chicago home.
If you try something on this list, please come back and let me know what you thought! And if there’s some place you’ve been/tried that’s not on the list, but you think it should be, let me know that too. I’ll go check it out for myself!
“A stranger visiting Chicago, seems to enter into a new world.”
