Home to the first recognized gayborhood in the country, Chicago is one of the biggest LGBTQ-friendly cities in the Midwest. Groups planning a trip in Chicago will find a variety of queer-owned, operated, and allied destinations in the Windy City.

Chicago Charter Bus Company is here to help your group travel safely and comfortably from stop to stop on your trip. Our bus rental services include private minibuses and full-size charter buses to shuttle you around Boystown, Uptown, Andersonville, and anywhere else in the city. Call 312-667-0906 to reserve a Chicago charter bus rental for a trip with friends to the annual Pride Parade or just for a group vacation at any other time of the year. Create your itinerary and travel on your own time to Chicago’s queer-centric businesses, performing arts centers, restaurants, and nightlife.

A group of people attending a LGBTQ Pride Parade

Local Queer-Owned and LGBTQ-Allied Shops

Shopping at Chicago’s LGBTQ-owned businesses is one of the best ways to support the city’s community. As you shuttle around the city from shop to shop, you’ll have to organize parking for your charter bus rental. Plan your shopping experience by Chicago neighborhood and reserve parking in each area.


Unabridged Bookstore in Lakeview and Women & Children First in Andersonville have both been Chicago staples for inclusive LGBTQ+ literature for more than 40 years. Women & Children First offers a curated selection of intersectional feminist literature, while Unabridged Bookstore has one of the biggest selections of LGBTQ+ literature in the country.

Unabridged Bookstore

Address: 3251 N Broadway, Chicago, IL 60657

Phone: (773) 883-9119

Women & Children First

Address: 5233 N Clark St, Chicago, IL 60640

Phone: (773) 769-9299


Gift and Home Stores

If you’re looking for gifts or small home furnishings, Humboldt House and Foursided will have you covered. Humboldt House is a woman- and queer-owned shop in Humboldt Park that features creative, locally-made homewares like artisanal candles, apothecary items, and handmade jewelry. Foursided is gay-owned and has locations in Andersonville and Lakeview. The shop provides custom art framing, vintage home decor, books, and indie greeting cards.

Humboldt House

Address: 1045 N California Ave, Chicago, IL 60622

Phone: (312) 785-1442

Foursided Andersonville

Address: 5061 N Clark St, Chicago, IL 60640
Phone: (773) 506-8300



Chicago has several LGBTQ-friendly and queer-owned clothing stores, including Brown Elephant Thrift Store and Vintuition. All proceeds from Brown Elephant benefit healthcare programs for Chicago’s LGBTQ community, as well as those who are uninsured and under-insured. Vintuition is a black- and queer-owned boutique store that offers vintage goods, upcycled clothing, and styling services.

A patron shopping at a thrift store

Brown Elephant Thrift Store

Address: 5404 N Clark St, Chicago, IL 60640

Phone: (773) 271-9382


Address: 1250 W Vanburen Chicago, IL 60607

Phone: (312) 550-5875


LGBTQ Arts and Performance Centers

Chicago has a vibrant and active queer arts community. Support local artists and performers by grabbing tickets to a show or film screening. Plus, when you travel with us, groups attending a packed event won’t have to worry about circling the roads to look for parking and inevitably missing the start of the show. Your driver drop everyone off for the show with plenty of time to spare.

Pride Arts Center

The Pride Arts Center is home to Chicago’s Pride Films & Plays non-profit organization. The center hosts screenings of local, national, and international queer films and theatre productions. Tickets can be purchased online for in-person events, and virtual programs are also offered on occasion.

Address: 4147 N Broadway, Chicago, IL 60613

Phone: (773) 857-0222

Jeezy’s Juke Joint

Jeezy’s Juke Joint opened in 2009 after owner Jeez Loueez noticed a lack of spaces in the burlesque world dedicated to Black performers. Today, Jeezy’s is a safe space for performers and audience members from all walks of life. Jeezy’s is a traveling burlesque revue but hosts regular shows in Chicago at The Promontory and The Newport Theater.

Chicago’s Dancers United

After losing multiple friends and colleagues to HIV/AIDS, professional dancer Keith Elliott started Dance for Life in 1992. This community fundraiser has been held annually ever since and has raised more than $6 million for HIV/AIDS prevention, treatment, and advocacy programs. Dance for Life grew into Chicago Dancers United, a non-profit organization that organizes dance fundraising events throughout the year.

Address: 200 West Monroe Street, Suite 1150, Chicago, Illinois 60606

Phone: (312) 922-5812

A group of friends drinking and eating

LGBTQ-Owned and Allied Restaurants

Need a bite to eat to fuel your busy day out in Chicago? There are plenty of restaurants around Chicago that are queer-owned and safe spaces for the LGBTQ community. Keep in mind, most restaurants in Chicago’s gayborhoods don’t have their own private parking lots. You’ll have to organize street parking or off-site public parking for your charter bus rental.

D.S. Tequila Company

If you’re looking for a savory mix of all-American fare and Tex-Mex, D.S. Tequila Co is for you. D.S. Tequila Company has become a cornerstone LGBTQ-friendly eatery in the Lake View area. It’s a popular spot during Chicago Pride to enjoy margaritas, tacos, and good company.

Address: 3352 N Halsted St, Chicago, IL 60657
Phone: (773) 477-0300

Jennivee’s Bakery

Jennivee’s is a proudly trans- and immigrant-owned bakery that serves up custom cakes, cupcakes, coffee, breakfast pastries, and other tasty treats. Grab a coffee and pastry when you’re craving something sweet during your Chicago trip.

Address: 3301 N Sheffield Ave, Chicago, IL 60657
Phone: (773) 697-3341

R Public House

Not only does R Public House offer tasty pub food like wood-fired pizza and chicken wings, but this popular Rogers Park bar and eatery also regularly hosts fundraisers for LGBTQ+, women’s, and immigrants’ rights causes.

Address: 1508 W Jarvis Ave, Chicago, IL 60626
Phone:  (872) 208-7916

Wilde Bar & Restaurant

The Irish owners of Wilde bar opened the Boystown establishment to directly challenge the perception that Irish pubs are conservative and unwelcoming to the LGBTQ community. Named after famous gay author Oscar Wilde, this upscale pub is a must-visit for literature lovers. Sit under the stained-glass skylights among cases filled with books and enjoy elevated pub fare like fish and chips, shepherd’s pie, and meatloaf.

Address: 3130 N Broadway, Chicago, IL 60657
Phone: (773) 244-0404


Gay Bars and LGBTQ Nightlife in Chicago

Whether your group wants to dance the night away or relax and sip drinks, Chicago’s queer nightlife scene has something for you. Worried about having to call rideshares or designating drivers for your night out? Rent a bus and leave everything up to a professional driver. You’ll have a built-in DD as you hop between lively nightlife spots in the Windy City.

A group of friends at a nightclub

Roscoe’s Tavern

Roscoe’s Tavern has been a Boystown hotspot since opening in 1987. Just think of visiting Roscoe’s as stepping into one giant party. This casual bar is great for dancing and has famous drink specials.

Address: 3356 N Halsted St, Chicago, IL 60657

Phone: (773) 281-3355


With a massive indoor dancefloor and multi-level outdoor patio, Sidetrack is one of the most popular queer nightlife spots in Chicago. Grab a round of alcoholic slushies and enjoy the DJ spinning dance tunes on the rooftop.

Address: 3349 N Halsted St, Chicago, IL 60657

Phone: (773) 477-9189

The Closet

The Closet opened in 1978 as a small lesbian bar and has been a neighborhood favorite ever since. It’s the perfect dive spot to sit with your group and chat over a few brews in a safe space.

Address: 3325 N Broadway, Chicago, IL 60657
Phone: (773) 477-8533

Big Chicks

If your group is an artsy bunch, Big Chicks is for you. This cash-only bar is located in a historic art-deco building and has walls lined with work from local artists. Big Chicks hosts concerts and themed nights on top of offering nightly drink specials and tasty food from the in-house restaurant.

Address: 5024 N Sheridan Rd, Chicago, IL 60640

Phone: (773) 728-5511


Travel with Chicago Charter Bus Company

It doesn’t matter how many stops are on your itinerary or how many people are in your group, Chicago Charter Bus has you covered. Forget the stress of finding your Uber in a sea of Pride Parade attendees or worrying about parking several cars as you rush to catch a dance showcase. Sit back and relax while the pros handle your transportation. Give the Chicago Charter Bus Company team a call at 312-667-0906 for a free, personalized quote.