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The Best Chicago Date Spots
18
items For when you want more than dinner… my round-up of Chicago’s most romance-friendly restaurants, cozy bars, and fun, slightly unexpected activities.
Map
Sections
3
Dinner Spots
Bars
Activities
Dinner Spots
For dim lights, shared plates, and a lively atmosphere – but not too loud for conversation.
The most underrated Italian gem on Milwaukee Ave in Avondale. Great for a date night (close to Logan Theater and Avondale Bowl) with an intimate, cozy vibe and great food. (Try the lasagna! Try the ceasar seared cabbage!)
void
This place is a favorite for a reason. The ambiance is so cozy (particularly on a winter night) and the food is amazing. Start the night out with champagne and oysters and try their delicious tikka masala.
The restaurant is usually booked up but you can get reservations up to 21 days in advance. Set a reminder for yourself a 9 a.m. when they become available. It's worth it!
The restaurant is usually booked up but you can get reservations up to 21 days in advance. Set a reminder for yourself a 9 a.m. when they become available. It's worth it!
Armitage Alehouse
Famous for their super thin, tavern-style pizza, this West Town spot is small and atmospheric – perfect for an intimate dinner and conversation. We sat at the bar and had a great convo with the server.
PIZZ'AMICI
A dimly lit River North staple that feels both classy and sultry. The amber glow and vintage library vibes set a moody tone, and the martinis (especially the espresso and lemon drop) are *chef's kiss emoji*. Don’t forget to stop by the photo booth do...
Gilt Bar
A lively Mexican-seafood spot in Pilsen that makes for a great dinner-show date night, seeing as it’s right below the historic Thalia Hall music venue. The restaurant offers refined seafood plates and seasonal cocktails that can help you wind up or d...
Mariscos San Pedro
This retro-inspired restaurant/cocktail bar in Bucktown serves up delicious, shareable Chinese-American food and is perfect for a li'l rendezvous with your boo. Whether you're staring into each other's eyes across a two-top or getting cozy at the U-s...
Chef’s Special Cocktail Bar
Bars
Strong drinks and cozy corners made for leaning in.
Weegee's is an often-underlooked (IMO) gem in the Logan Square area. An upscale corner bar offering classic cocktails, a mellow ambiance, and unpretentious vibes, it's a great place to bring a date for a nightcap and a game of shuffleboard. Plus it h...
Weegee's Lounge
A Wrigleyville classic just two blocks north of Wrigley Field, this friendly tavern is one of the less crowded dive-bar options in the area, making it a great stop after a Cubs game date or a show at The Metro. It’s got a rotating draft list and regu...
The Gman Tavern
A speakeasy-style cocktail bar tucked behind a Chinatown restaurant that’s perfect for a drink after exploring the neighborhood. The vibe is intimate and stylish, with Asian-inspired craft drinks and snacks. It's a nice balance between lively and low...
Nine Bar
Through the Record Shop you'll find Dorian's, a low-lit lounge with vinyl, cocktails, and live music. This spot features regular live performances and DJs spinning eclectic sets, and it’s an intimate place to enjoy good drinks and great music without...
Dorian’s
This dive-bar-meets-tropical-lounge in Bridgeport is worth the trip for a date night. With sp00ky drinks, fun decor, and a vibe that’s both playful and relaxed, it’s an ideal spot to spark conversation, especially on a first or second date. Great for...
Electric Funeral
Another Logan Square staple, you'll step inside Scofflaw to find rich wood accents, Victorian-era–inspired sofas, and cozy nooks that create a really relaxed, intimate vibe. This spot is perfect for conversation over expertly crafted cocktails.
Scofflaw
Activities
For when you want to *do* something (aside from the obvious) on your date.
A classic bowling alley with retro vibes and analog score-keeping that keeps things fun and interactive. Whether it’s your first date or your hundredth, keeping score the old-school way gives you something to laugh about (we made good friends with th...
Avondale Bowl
A mini-golf spot that’s perfect for a date night. The themed courses and cocktails keep things light and competitive, and since it’s in Fulton Market, you’re surrounded by tons of fancy bars and restaurants. It's an easy (dare I say wholesome) activi...
Puttery
The perfect date spot to show off your gaming skills (or lack thereof). Unlike nearby Emporium’s larger, louder crowd, Logan Arcade has a more relaxed vibe with classic arcade games, pinball, and plenty of space to chat between games.
Logan Arcade
This tropical-themed shuffleboard club in Wicker Park is a mix of fun cocktails, retro beach-style décor, and oversized games like giant Jenga. A great spot for a double date.
Royal Palms Shuffleboard Club
Who doesn't love an excuse to get dressed up for a fancy dinner followed by a show? You can catch all types of performances at Chicago's beautiful art-deco opera house, including classic opera, a ballet by the Joffrey Ballet, or a special concert eve...
Lyric Opera of Chicago
The Salt Shed brings together great music and a selection of food and drink vendors to make each show feel almost like a mini festival, but much more laid back. This indoor/outdoor venue is one of my favorites in the city, especially when you're able...
The Salt Shed