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Two Gay Expats - Chicago - USA

As one of the most exciting cities in the USA, Gay Chicago is home to Boystown, the first designated gay neighborhood in American history. Located in the Lakeview neighborhood of Chicago, Boystown is most famous (or infamous!) for the sheer number of gay bars, clubs, and restaurants along North Halsted Street. Each summer, more than a million LGBT+ and allies come out to celebrate Chicago Pride and Northalsted Market Days, the largest street festival in the Midwest. 

Another gayborhood on Chicago’s north side is Andersonville. Known for its Swedish roots and iconic water tower, Andersonville is home to one of Chicago’s largest LGBT+ populations. Along busy Clark Street, you will find an incredible array of shops, restaurants, and bars. Andersonville is also known as Chicago’s shop local capital.

With so much gay pride in one magnificent city, should you include Gay Chicago on your travel list? Read on to find out! 

Two Gay Expats - Chicago River- Architecture Tour
Chicago River
Two Gay Expats - Chicago - Sears Tower Skydeck
Sears Tower Skydeck - Chicago, IL

Overview – Located on the shores of Lake Michigan, Chicago is the third largest city in the United States. Famous for it’s skyline and amazing architecture, restaurant scene and deep-dish pizza, and some of the best museums in the country,  Chicago also entertains visitors and residents alike with its fabulous music and theater venues. For the fifth year in a row, Condé Nast Traveler readers ranked Chicago the No. 1 big city in the U.S., and we couldn’t agree more!

Top 10 things to see and do in Chicago

1
Walk, run, or cycle the Lakefront Trail Hire Lyft's Divvy bikes, which can be found all over the city, and enjoy the city views and people watching along this 18.5-mile shared path.
2
Visit the Art Institute of Chicago Enjoy one of the world's best collections of Impressionist Art. We rank this museum's collection up there with Paris' Orsay Museum and New York's MET.
3
Take a selfie at The Bean Snap the requisite photo for the 'Gram here in Millennium Park or head up to the nature boardwalk and pavilion in Lincoln Park for an iconic skyline shot!
4
Relax on the beach You heard that right! Chicago has 24 beaches along freshwater Lake Michigan. Our favorite is Kathy Osterman (aka Hollywood Beach) which is also the gay beach. And for gay dog dads, head to Montrose Beach.
5
Eat deep dish pizza at Pequod's Chicago is famous for its deep dish pizza, and the best of the best is local favorite and super popular Pequod's.
6
Explore Andersonville Head up to Andersonville, Chicago's shop local capital and one of the largest LGBT+ communities in the city, for brunch, shopping, gay bars, and more!
7
Watch sunset from LH Rooftop Make a reservation and head up to the rooftop at LondonHouse for the best sunset in the city!
8
Listen to live jazz at Green Mill A nod to Paris' Moulin Rouge (Red Mill), this entertainment venue in Uptown was a favorite of Al Capone. We love Friday nights here (early!) to listen to jazz on the organ.
9
Bar hop in Boystown Arrive early to avoid lines and bar hop down busy Halsted Street! We love Sidetrack with their indoor and outdoor space and frozen cocktails.
10
Head to Riverwalk Take a stroll on Chicago's Riverwalk with gelato...or stop for wine? Or both? Before leaving Chicago, it's a 'must do' to walk this park on the Chicago River along with taking an Architecture Cruise!
Two Gay Expats - Chicago - Hollywood Gay Beach - Kathy Osterman Beach
Kathy Osterman / Hollywood Gay Beach

When to go – We love Chicago in the summer! The city comes alive and the Lakefront Trail and gay beaches are packed! We particularly love Chicago in August for Market Days! 

Two Gay Expats - Chicago - L Train
Red Line "L" Train

Getting here – Chicago is home to not one but two well-connected airports to the downtown Loop or city center. With both American and United Airlines maintaining hubs at O’Hare Airport (ORD) in the northwest corner of the city, you will likely find competitive prices and direct flights when flying to Chicago. In addition, Southwest Airlines maintains a hub at Midway Airport (MDW) to the southwest of the city. You can reach the Loop from both airports on public transit known locally as the “L” or elevated train. To reach Boystown or Andersonville, you will have to change lines in the Loop, or alternatively, you can take either Lyft or Uber from either airport. 

Pro tip – There is no need to wait in line to buy a transit card, you can simply tap your enabled credit card with tap icon or phone/device using Apple Pay, Google Pay, Samsung Pay, and Fitbit Pay. Transfers are enabled with these options as well if you are transferring from the blue line to the red line to get from O’Hare to Andersonville for example. 

Two Gay Expats - Chicago - LondonHouse Rooftop Sunset
LondonHouse Rooftop Sunset

Where to stay – In our opinion, the best hotel in Chicago is LondonHouse. We enjoyed a staycation here after our legal wedding (we got married in Tulum, Mexico) and have been to the rooftop for sunset many times. The hotel is in walking distance to Riverwalk, the Architecture Tour, Millennium Park and The Bean, Art Institute of Chicago, shopping along the Magnificent Mile, Navy Pier, and the Lakefront Trail where you can grab a Divvy bike and head up to Boystown, Lincoln Park, or the Hollywood gay beach! 

Other excellent gay-friendly boutique properties that we love are the The Intercontinental Chicago Magnificent Mile. The romantic junior Olympic-size swimming pool was completed in the late 1920’s and was an engineering marvel at the time given it’s position on the hotel’s 14th floor!

We also love The Robey in Wicker Park for something more unique as well as the highly-rated and cozy Guesthouse Hotel in Andersonville. On that note, there are not many hotels in or near Andersonville, thus don’t forget Misterbnb as an option to stay with a gay local! We loved our Misterbnb stay in Andersonville before our cross-country train trip from Chicago to Portland on the Amtrak Empire Builder.

If you are looking for an excellent budget option, we recommend The Freehand where Trai spent a month when backpacking. The hotel is just a few minutes walk from LondonHouse so it’s also in a prime location to explore Chicago. The Freehand also has a small gym, a popular bar called Broken Shaker, and offers rooms from penthouse suites to shared quad rooms. 

Where to eat and drink – For the best restaurants and bars in Chicago, we have you covered. 

For breakfast, our low key ‘go to’ favorite is Dollop Diner in Andersonville. If you have a sweet tooth, the best pancakes in Chicago can be found at The Bongo Room just a few doors down. Speaking of sweets, bakery-cafe Lost Larson serves up the best cinnamon roll we’ve ever had. Another tasty and popular spot is Taste of Heaven. For an LGBT+ staple, don’t miss Uptown’s Tweet. 

For lunch, we highly recommend Replay in either Andersonville (our favorite) or Boystown. Both locations are extremely popular with the gay community. We love the huge selection of local craft beers on tap and the super fun and friendly vibe. We are also huge fans of Lady Gregory’s in Andersonville. Lady G’s offers upscale but casual elegance with excellent food and service. Wilde Bar and Restaurant in Boystown is equally as fabulous and loved by the LGBT+ community. 

To list our favorite dinner spots is tough, as Chicago is a foodie’s paradise. In Boystown, our favorite restaurant is Wood. It’s the perfect location as well to reserve before a night out at Sidetrack, Roscoe’s Tavern, and dare we say late night at the Shoe–but let’s not jump ahead as we’ll cover all of these in more detail below in Where to find gay nightlife!

Back up in Andersonville, Hopleaf is one of the best gastropubs in Chicago. Be sure to explore the different rooms and back garden. Their list of local craft brews and beers from around the world is impressive. For sushi, BYOB favorite Ora is the best. For Italian, try Calo, which is also a great option for large groups. We really enjoy sitting at the bar here! 

Of course, all of these recommendations are for the best restaurants and bars popular with the LGBT+ community. Chicago also has tons of much fancier or popular restaurants like Alinea, Chicago’s only 3-star Michelin rated restaurant, or Girl & The Goat of Top Chef’s Stephanie Izard fame. We have focused on places locals frequent…and that you won’t find recommended everywhere! 

Where to find gay nightlife – Saving the best for last, we are super excited to share our list of the best gay bars, lounges, and clubs in Chicago! We’ve alluded to a few already, so lets dive a little deeper. 

For the most popular gay bar in Chicago, head over to Sidetrack. They have multiple rooms, an outdoor space, coat/bag check, signature frozen cocktails, and so much more. Also, don’t miss show tunes. We took Trai’s mom to Out at Wrigley (a gay pride event to watch a Chicago Cubs baseball game as a community) and then to show tunes at Sidetrack. We may have ended up a few hours later on the Ferris Wheel at Navy Pier, but the point is when asked what she loved most about Chicago, she responded, “Show tunes at Sidetrack. And the architecture tour.” There you go! Sidetrack is also EPIC during Market Days, which is not to be missed! 

Across the street from Sidetrack is Roscoe’s, which is another multi-room gay bar and club. Roscoe’s is a super fun place to go dancing, but head over early if you want to avoid the huge lines on the weekend!

For late night shenanigans, we have been going the Shoe for years! Lucky Horseshoe Lounge that is. It’s a fun, no frills gay lounge and strip club. 

Although the itinerary above is perfect for a night out in Boystown, don’t forget Chicago has a second huge gayborhood about 2-3 miles north of Boystown that we haven’t even covered yet! 

In Andersonville, we recommend the bar at Replay to warm up. Other good options are the SoFo Tap for low key drinks or brews or even Big Chicks just a short walk to neighboring Uptown.

To take it to the next level, head to Meeting House which is crazy popular and gets absolutely packed! They have drag performances on the lower level and games (including skee ball) on the upper level.

For a nightcap, and our favorite spot for martinis, don’t miss Marty’s. It seemed like forever until they re-opened, but we’re so glad they did! It’s a cozy space and easy bar to meet people. 

Well, there you have it. Our favorite gay bars, lounges, and clubs in Chicago! As a bonus, if you are staying at LondonHouse or Freehand or nearby, there is one old school gay bar downtown called Second Story. Enjoy! 

Other Services

Banking – There are a variety of banks (and ATMs) throughout the Loop, Boystown, and Andersonville. You will have no trouble finding one in any of these areas. 

Barbershop – To keep it fresh, Edgewater’s Father and Son is perhaps the best barbershop in Chicago and is consistently busy with gay men. Before the pandemic, you could add your name to a chalk board on arrival noting your preferred barber, but now it’s reservation only via the app which we prefer. 

Two Gay Expats - Chicago - Andersonville - Cheetah Gym
Cheetah Gym - Andersonville, Chicago

Fitness/Gym– The best gay gyms in Chicago are Cheetah in Andersonville and LAC in Boystown. Both gyms offer day passes but please call ahead to confirm this policy remains in effect. 

Wine/Liquor store – Our favorite local wine shop and liquor store is Andersonville Wine & Spirits. It’s the perfect stop to grab a bottle of wine before heading to BYOB fave Ora for sushi as well. In Lakeview, Binny’s Beverage Depot is huge and very popular. 

*** To see more of our gay adventures, head over to our YouTube Channel and be sure to subscribe! And, of course, follow us on social media @twogayexpats for more gay travel inspiration!