Gay bar · Uptown
3
"Part of the 2Bears Tavern Group — Mark Robertson discussed how the tax hike could force them to raise prices, potentially affecting customer turnout and tipping behavior." - Leigh Giangreco
Steak house · Loop
This upscale steakhouse couples classic dishes with a luxe vibe, featuring perfectly cooked steaks and a chic patio for cigar lovers.
23 Postcards
Restaurant · Near North Side
Warm restaurant with a striking bar & a terrace offering Spanish tapas & sangria.
4 Postcards
Brewery · Bridgeport
Hip warehouse setting for drinking small-batch local beers with snacks, sandwiches, coffee & tea.
29 Postcards
Wine bar · Roscoe Village
New American sharing plates & an extensive wine list in a small storefront with booths & a patio.
12 Postcards
Restaurant · River North
Multilevel tavern offers European-influenced dishes & old-fashioned cocktails in antique surrounds.
Hot dog restaurant · Lakeview
This cash-only joint serves mouthwatering hot dogs, juicy burgers, and crispy fries—perfect for a casual bite that won’t break the bank.
10 Postcards
Hotel · West Town
The Emily Hotel is a chic gem in the West Loop, blending modern comfort with a warm vibe, featuring a stylish café, rooftop bar, and prime dining options nearby.
14 Postcards
American restaurant · Logan Square
A cozy hipster gem serving inventive farm-to-table dishes and craft cocktails, where the whiskey flows and the ambiance is perfectly chill.
44 Postcards
Italian restaurant · Near North Side
Pasta, steaks & seafood served in a sleek, group-friendly eatery backed by Giuliana & Bill Rancic.
25 Postcards
International airport · Chicago Midway International Airport
Airport serving the Midwest & featuring direct train service to Chicago.
3 Postcards