Guide to Gay Chicago: Gay Bars, Gay Neighbourhoods, Pride Fest Chicago & so much more!

Chicago impressed us on so many levels. It is a beautiful Midwestern city, with super friendly people, lots to keep you busy and an incredibly diverse and thriving gay scene.

Gay Chicago has a lot to offer and from our experience, the whole city appears to embrace and support its LGBTQ+ community.

We felt very safe, at ease, and welcome here as a gay couple. We never felt like we needed to look over our shoulder, fear holding hands or showing affection: just as its should be!

Our first visit was over the Chicago Pride Fest weekend and was hosted by Choose Chicago so we really got to see just how gay Chicago can be!

In our Gay Chicago Guide, we will cover the gay neighbourhoods of Chicago, gay bars, Gay Pride Fest as well as what activities we did, where we stayed and ate so you will have all the information you need to plan your own visit!

Let’s get started!

Gay chicago guide skyline

Gay Neighbourhoods in Chicago

Chicago has two very distinct gay neighbourhoods, Boystown and Andersonville (affectionately known as MANdersonville).

Boystown

When you are looking into gay Chicago, Boystown will and should be, right at the top of your list.

Boystown was the first officially recognised gay community in the US. It’s streets and crossings are lined with rainbows and it was named the “best gay neighbourhood in the world” by Out Traveler magazine!

It should come as no surprise that Boystown is the place to go for gay bars and clubs during the evening, but also for drinks and dinner during the day. It really feels like a little gay utopia where things have been turned on their head and its homonormative here not heteronormative!

Look out for the plaques that line the streets on decorative pillars that commemorate either an LGBTQ hero or heroine from history or a significant LGBTQ historical event.

Check out some of the gay bars in Boystown further on in this guide.

Andersonville

Andersonville is the second major gay neighbourhood in Chicago and has it own unique charm which is quite different to Boystown.

Andersonville is a small gay neighbourhood, but is one of the highest populated LGBTQ areas of Chicago. Again, this felt like a small gay utopia within the big city.

It boasts many LGBTQ+ owned businesses from trendy cafes, to independent shops and restaurants.

Make sure you check out these shops:

  • Cowboys and Astronauts: a gay lifestyle shop with everything from clothing to styling products, accessories and décor. A really cool place with lovely owners. We really loved their explanation of their store to explain it as a safe space for anyone from the LGBTQ+ community, for example a newly trans person looking for their first shaving product could feel safe to have that open discussion here.
  • Women and Children First Bookstore: lesbian founded and co owned bookstore which has lots of LGBTQ+ material.
  • Strange Cargo Tees and More: This shop was a lot of fun. It had a lot of LGBTQ+ themed merchandise and a lot of funny stuff!
Gay chicago guide andersonville
Andersonville

Gay Bars in Chicago

You can find gay bars all across Chicago but the majority are found in Boystown and Andersonville. We went to Sidetrack twice during our trip and loved it!

Here are some options to keep you busy!

Sidetrack – Boystown

Sidetrack was a finalist in Logo Tvs ‘Best Gay Bar in the World’ and we can see why!

It has plenty of rooms to explore depending whether you want to chill, chat, or dance the night away!

For us we were mainly on the dance floor which has a huge screen playing music videos to go alongside the music.

Sidetrack plays a lot of pop, retro and throws the occasional show tune in there to!

Drinks are reasonable and the crowd is relatively young and mixed.

Address: 3349 N Halsted St, Chicago, IL 60657, USA

Gay chicago guide gay bar sidetrack
The boys of Sidetrack!

Big Chicks – Uptown

This is a chilled out gay bar for food, drinks and fun.

The crowd is mixed with men and women of all ages. The narrow room and dance floor become crowded on weekends with DJs playing Friday and Saturday.

Address: 5024 N. Sheridan Road

Kit Kat Lounge & Supper Club – Boystown

This is a popular place to hangout in Boystown and has performances from local drag queens.

Address: 3700 N. Halsted Street

Roscoes

Another one for Boystown. Roscoes offers Djs and drag to a young fun crowd.

Address: 3356 N Halsted St

Charlies Chicago – Boystown

Charlies has a wild west vibe with cowboys dancing to country and western music. However, come 1am on a weekend this turns into a go-go boy after hours dance club!

Address: 3726 N Broadway

Hydrate – Boystown

This is one of the bars to head to if you are looking to go all night.

It starts to get busy from midnight onwards and you can expect DJs and the occasional drag show. Hydrate is open until 4am Friday/Sunday and 5am Saturday.

Address: 3458 N Halsted St

The Call – Andersonville

If you want to dance but aren’t heading to Boystown then this is a great option in Andersonville. This is a video and dance bar and plays a lot of pop.

Address: 1547 W Bryn Mawr Ave

Atmosphere – Andersonville

Atmosphere is known for its scantily clad dancers, drink specials, large dancefloor and upscale dive bar vibes. One to check out if you are in Andersonville.

Address: 5355 N Clark St

Little Jims – Boystown

This was Boystown’s first gay bar and is open to 4am everyday – one for a late night!

Address: 3501 N Halsted St

Gay Events in Chicago

Gay Pride Fest Chicago

Gay Pride Fest Chicago is huge with crowds topping a million people!

There are many events throughout the week leading up to the main parade, make sure you check out the ones we attended:

  • Second City’s Salute to Pride: This is only on during Pride and is a new, all queer variety show full of drag, comedy and an all LGBTQ+ cast.
  • Pride in the Park: this is the day before the parade. Pride in the Park is an all new event as of 2019 at Grant Park. There were drag acts, stalls for drinks, food, shopping and of course the main stage where they had international performers including Iggy Azalea. This was a full-on fun in the sun event (with lots of hot guys to check out)!

When it comes to the parade, there are over 200 floats with eye catching costumes, bright colours and music! We really felt that the whole city came together at the Chicago Pride Parade in support of the LGBTQ community.

This year we were in the parade with the Chicago White Sox float and loved the positive energy from the crowds! It was an amazing experience.

Gay chicago guide pride parade
Chicago Pride Parade

Admission to the parade is free, and all ages are welcome.

Northhalsted Market Days

At any time of the year Boystown is the place to go for the biggest gay scene, however for Northhalsted Market Days it explodes!

Northalsted Market Days is the largest street festival in the Midwest held in August each year.

The festival runs over the weekend and features live music on 4 stages, 200+ unique vendors, arts, crafts, food and drink, DJ’s and dancing, sponsor booths, and more!

From the pictures we have seen, we are definitely keen to return to Chicago for this event!

Andersonville Midsommarfest

Midsommarfest is two days and three nights of music, dancing, kids’ entertainment, and delicious food in Andersonville during June.

There are also lots of stalls with local merchants during the day and then you can head to one of the bars mentioned above come the evening.

Backlot Bash

This is the most popular and highly attended lesbian event in Chicago. It is held for 3 nights in June/July each year in Andersonville behind the Cheetah Gym.

Activities to do in Chicago

There is so much to do in Chicago! We stayed for 5 nights in total and were kept very busy, here are our top 6 activities in Chicago from our stay:

Legacy Walk Tour by the Legacy Project Chicago

This was an excellent and education LGBTQ+ tour of Boystown

In Boystown, half a mile of the North Halsted corridor is lined with 20 beautiful pillars showcasing 37 plaques of significant LGBTQ+ people throughout history. It’s the only architecturally-defined LGBTQ neighborhood on earth!

During this tour we visited and learnt about some of these people. We did not recognise all the names straight away, but we certainly won’t forget them. If you want to be inspired, check out this tour.

Skydeck

This is an absolute must!

Get the elevator up to over 400m to get the best view of the city! Not only that, but there are 4 clear platforms sticking out the side of the building which you can stand on and see all the way down to the sidewalk – it’s a long way down!

This was a lot of fun even though heights make Sion feel dizzy! If you are feeling brave, stand on the platform and jump (Ben did)!

The cost to go up is $25 and you can read more here.

Gay chicago guide skydeck
Sky high at the Skydeck!

Millennium Park

For concerts, exhibitions, tours, family activities and a place to relax within the city head to Millennium Park.

If it is a sunny day we recommend grabbing a picnic and coming to the park. You will also find the iconic Chicago ‘bean’ in the park – you can’t miss it!

Gay chicago guide millennium park
Millennium park

Architecture River Tour

We didn’t think we were interested in architecture, but this was actually a really interesting and fun tour.

The main reason we loved it was because viewing and exploring the city by river was unique and helped show us how beautiful the city really was.

We also like the fact that the guides and staff on board had a lot of personality! Don’t just take our word for it, this activity is one of the highest rated activities to do on TripAdvisor!

The cost is $43 per adult and the tour lasts 1.5 hours. For full details check out their website.

 

Field Museum

This was 100% our type of museum.

The largest and most intact T-Rex skull in the world, Egyptian tombs and bug experience had us completely sold.

For us, the dinosaur section is worth the visit alone and we would have easily stayed for hours had we had time.

Take at least half a day here and you will not be disappointed!

Friday Night Flights at Chicago Brewing District

This was the start to our night out in Chicago!

Friday Night Flights is held weekly during the summer (check here for when it is on). Local breweries all come together, along with food stalls and a DJ to create fun, summer, beer filled evenings.

You pay $20 in advance or $25 on site for a ticket to sample 10 beers (you might get more if you are nice!).

Even though Sion does not like beer, there were lots of fruity beer options that kept him happy!

If you fancy something chilled, outdoors and you like beer, get yourself here!

Chicago City Pass

There are so many more things to do and actually some of the activities above are included in the Chicago City Pass.

The pass is valid for 9 days and provides prepaid, premium admission to:

  • Shedd Aquarium
  • Skydeck Chicago
  • Field Museum
  • Alder Planetarium OR Art Institute of Chicago
  • Museum of Science and Industry OR 360 Chicago Observation Deck

The pass is $108 and the value of the above activities $214. Essentially, if you plan to do more than two activities in Chicago then this is definitely worth getting.

For more info see here.

Gay Friendly and Gay Hotels in Chicago

We only stayed at one hotel during out stay which we loved. The other hotels we suggest are based on recommendations from friends and research.

Kimpton the Gray

This is the hotel we stayed at and we loved it. The service was excellent, the style was luxurious, trendy and modern and the location ideal for exploring the city. We also loved the fact it was a pet friendly hotel for those of you who want to bring your furry friend!

We highly recommend this hotel based on our own experience. You can check rates and book here.

Best Western Grant Park

If you are on more of a budget, consider the Best Western. It is an older hotel, simple in design and its main selling point is its location right next to many popular attractions including the Field Museum.

You can see more and book here.

Best Western Plus Hawthorne Terrace

As above, a good affordable option. The main pro with this hotel is that it is located in Boystown so there is no need for expensive taxi journeys if you are in Chicago for the gay nightlife!

Book here.

City Suites Hotel

This hotel is in Lakeview/Boystown so perfectly located for a night out. It’s an small Art Deco style hotel, gets excellent reviews and TripAdvisor and is next door to the ‘L’ train which is very convenient.

Take a look and book here.

Where to eat in Chicago

We ate so much in Chicago, we were constantly full. Here is where we ate and fully recommend:

  • Boleo at Kimpton Gray – this was a trendy rooftop bar with food on the 15th floor of our hotel. We loved the shrimp skewers!
  • Lou Malnati’s Gold Coast – This one is specifically for the deep dish Chicago pizza, you can’t leave Chicago until you have tried one!
  • Zed451 rooftop – Another beautiful rooftop bar with a stylish restaurant serving more meat than we could handle. The waiters here serve to your table all kinds of steak, sausages, chicken and lamb until you can’t eat anymore. The food was amazing and the service top class.
  • Lady Gregory’s Andersonville – make sure you explore Andersonville and when you do, stop here for lunch. They have a cool menu, creative cocktails and a friendly vibe.
  • Drew’s on Halsted – following our beer tasting we headed here for a meal in Boystown before our night out. The cocktails were great, the meal delicious and we ended up dancing as there was a DJ!
  • Latinicity – one for a quick lunch stop. This is a collection of fast food places in one food hall ranging from healthy salad options, to Asian cuisine and Mexican.
  • TAO Chicago – Save this for your final meal or for an occasion. This was the most stunning place we ate in Chicago and well worth dressing up for. The food is a mix of Asian styles and absolutely delicious. After your meal they open a club upstairs.
  • River Roast – finally, if you need a home cooked meal or are feeling a little delicate go and get yourself a hearty roast family style at River Roast. Again, we left stuffed!

Gay chicago guide fountain

Chicago ticks all the boxes when it comes to being a gay travel destination. It’s gay scene it well established, diverse, fun and is well rooted into the city and society. It also ticks all the boxes in terms of activities, food and atmosphere – its such a friendly place and we will have to return again one day!

We hope you found that guide useful, let us know about your experience or if you plan to visit!

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Note:  Our trip was hosted by Choose Chicago. This post also has affiliate links. You won’t get charged any extra for using the link but we will receive a small commission for each referral. Please note, all opinions are still our own. You are not obligated to use the links but we appreciate it if you do. Thanks.

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