Deep dish, deep pours, deeper memories
Second City improv, Wrigley/Cubs games, rooftop bars, deep-dish, speakeasies, River Walk brunch. The Midwest city-bachelor default.
boat cruise • 1.5 hours
Iconic river cruise through downtown architecture
golf • 2-3 hours
Driving range bays with food, drinks, and games
escape room • 2 hours
Legendary improv theater that launched countless comedians
axe throwing • 1.5 hours
BYOB axe throwing in West Loop
club • unhinged • $$$
Multi-level dance club in River North with top DJs
Dress code: Upscale nightlife attire, no athletic wear
rooftop • balanced • $$$
Stunning rooftop views of the skyline with craft cocktails
Dress code: Smart casual to upscale
speakeasy • chill • $$$
Award-winning Wicker Park cocktail lounge with no-sign entrance
dueling piano • unhinged • $$
Dueling pianos and sing-alongs perfect for party groups
tiki bar • balanced • $$$
Underground tiki bar with elaborate rum cocktails
bar • unhinged • $$
Wrigleyville party bar with live music and BBQ
bar • balanced • $$
Legendary Lincoln Park blues club with two stages
rooftop • balanced • $$$
World's largest rooftop deck at Navy Pier
Dress code: Smart casual to upscale
sports bar • balanced • $
Wrigleyville staple with batting cages upstairs
Italian • $$$$ • Best for: group-dinner
Celebrity-backed River North Italian with massive portions
American • $$ • Best for: late-night
Legendary double cheeseburger worth the wait
Pizza • $$ • Best for: dinner
The quintessential Chicago deep dish experience
New American • $$$ • Best for: group-dinner
Stephanie Izard's flagship with bold, shareable plates
American • $ • Best for: late-night
Chicago institution for Italian beef and hot dogs
New American • $$$ • Best for: brunch
Gorgeous Millennium Park views with upscale brunch
Steakhouse/Seafood • $$$$ • Best for: group-dinner
Top-tier surf and turf in River North
Mexican • $$ • Best for: dinner
Wicker Park taco joint with whiskey and great patio
hotel • Max 2 guests
5-star riverfront luxury in the heart of downtown
boutique-hotel • Max 2 guests
Trendy Fulton Market hotel with rooftop bar
airbnb • Max 12 guests
Full houses near Cubs bars and nightlife
hotel • Max 2 guests
Party-friendly hotel with rooftop lounge and great vibes
airbnb • Max 10 guests
High-rise condos walking distance to everything
boutique-hotel • Max 4 guests
Warehouse conversion in Fulton Market with a rooftop pool, cinema, and design-forward rooms.
boutique-hotel • Max 3 guests
Art Deco tower in Wicker Park with a two-story penthouse bar and neighborhood-cool energy.
hotel • Max 4 guests
Gold Coast boutique hotel steps from the Magnificent Mile — stylish rooms and a rooftop pool.
airbnb • Max 10 guests
Whole-home rental in a classic Chicago greystone — full kitchen, private yard, and neighborhood walkability.
airbnb • Max 12 guests
Full houses near Cubs bars and nightlife
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