Welcome to Chicago’s enchanting date bars, where the romantic vibe of the city is truly felt. Whether you’re fostering a new relationship or igniting an old one, Chicago has an abundance of small venues that provide the ideal atmosphere for an unforgettable date night. Every location has its own charm, from rooftop bars with breathtaking views of the skyline to speakeasies with dim lighting and vintage charm. Come along with us as we explore some of Chicago’s most charming and romantic date spots across its many neighborhoods. With carefully chosen drinks, warm lighting, and a distinct vibe that makes each of these bars a special haven for romance and connection in the Windy City, elevate your evenings.
If you’re looking for places to go out with your date, Bar Siena, situated on restaurant row in Chicago’s West Loop neighborhood, is an easy-going Italian restaurant with plenty of charm. Their drinks menu includes something for everyone, from cocktails (both zero proof and alcoholic), American beer and seasonal offerings like Italian frozen treats.
Situated in Wicker Park, an area known for trendy restaurants and great food, this James Beard award-winning bar oozes sophistication in its decor and signature cocktail series. The Violet Hour is a bar for cocktail enthusiasts. They specialize in cocktails and rare offerings, including an entire page of just bourbon options.
Arbella is a comfortable cocktail bar in the gallery-filled River North area. This relaxed lounge is one of those fun places to get drinks, serving great cocktails and bar snacks with a DJ in-house from Thursday to Saturday night. Check out their globally-inspired cocktails and visit countries worldwide without leaving the building.
Also situated in the West Loop, one of the best date bars in Chicago is the Lone Wolf Tavern serving up an old-school vibe with modern amenities. Food is provided by visiting restaurants like the Tamale Guy. Try one of their cocktails or enjoy a local craft beer on draft with your date.
If you want a curated experience, look at Wicker Park and the bordello-themed speakeasy Bordel. With jazz musicians, local DJs, and cabaret dancers, it provides some of Chicago’s most exciting evening entertainment with exciting drinks. Their drinks menu blends classics like daiquiris with Spanish coffees and a robust wine list.
The best way to describe Gilt Bar is vintage. It’s sophistication without being pretentious. Based in the trendy River North neighborhood, it should be on your list of where to get a drink. Gilt Bar focuses on doing the classics well but offers a splendid selection of agave drinks and non-alcoholic choices.
Set below Franklin Street in the River North district, I think the Franklin Room is one of Chicago’s top fun places to go out. Part restaurant and part bar, it’s a city tavern with elements of a classy speakeasy. The Franklin Room offers a variety of drinks, including brown liquor-based cocktails, beer, and sakes.
As the name suggests, Cindy’s Rooftop is a rooftop hotel bar in the Chicago Athletic Association hotel overlooking Millenium Park and Lake Michigan. Its gorgeous view makes it one of the best date bars in Chicago. Cindy’s offers signature cocktails like the Figgy Stardust, plus a good selection of wines.
Why should you trust us?
We use our own local experience and contacts in the city to know which places to include in our lists. We also researched the web and read 5 reputable blogs and websites, including ambiancematchmaking.com, timeout.com, theinfatuation.com, chicagodrinksguide.com, and theinfatuation.com. So that you can be sure you’re receiving the best of the best. We compiled all the results in one spot and ranked them according to how frequently they were referenced.