The Complete Gay Chicago Travel Guide: Chicago is one of the best gay-friendly cities in the USA. It is a beautiful Midwestern city, with super friendly people, lots to keep you busy and an incredibly diverse and thriving gay scene.
In this Gay Chicago Guide, I will cover the gay neighbourhoods of Chicago, gay bars, Gay Pride Fest, the gay beach, as well as what activities I did, where I stayed and ate so you will have all the information you need to plan your own visit!
Gay Chicago has a lot to offer and from my experience, the whole city appears to embrace and support its LGBTQ+ community. It also has a long standing history of not only supporting, but being a driver and advocate in advancing LGBTQ+ rights.
I felt very safe, at ease, and welcome in Chicago as a gay traveller. I never felt like I needed to look over my shoulder, fear holding hands or showing affection: just as it should be!
Let’s get started!
Is Chicago Gay Friendly?
Yes! Chicago is one of the most gay friendly cities in the US, along with cities like New York and San Francisco.
The city has a long standing history when it comes to LGBTQ+ activism, a thriving LGBTQ+ population and plenty of LGBTQ+ venues to welcome you. The wider state of Illinois is also considered to be one of the most gay friendly states in the US.
Read more about other gay friendly cities in the US like New York in my Gay New York Travel Guide or San Francisco in my Gay San Francisco Guide.
Gay Neighbourhoods in Chicago
Chicago has two very distinct gay neighbourhoods, Northalsted (previously known as Boystown) and Andersonville. So if you are looking for the gay area of Chicago, these are the places to start.
Let me share a little more about each of these gay areas in Chicago below:
Northalsted (aka Boystown)
If you are planning a gay trip to Chicago, Northalsted should be right at the top of your list.
Northalsted 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 Northalsted 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 Northalsted.
Andersonville
Andersonville is the second major gay neighbourhood in Chicago and has it own unique charm which is quite different to Northalsted.
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, see below.
Gay Bars in Chicago
You can find gay bars all across Chicago but the majority are found in Northalsted and Andersonville. I went to Sidetrack twice during my trip and loved it!
Here are some options to keep you busy, for a full list, read my dedicated guide to the best gay bars in Chicago (Northalsted and Andersonville).
Sidetrack – Northalsted
Sidetrack was a finalist in Logo Tvs ‘Best Gay Bar in the World’ and I can see why!
It has plenty of rooms to explore depending whether you want to chill, chat, or dance the night away!
I was mainly focused 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
Roscoes
Another one for Northalsted. Roscoes offers crazy drinks offers, Djs and drag to a young fun crowd.
Address: 3356 N Halsted St
Hydrate – Northalsted
This is one of the bars to head to if you are looking to go all night (it is a little more ‘circuity’).
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
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
Chicagos Gay Beach
Yes! You read that right, Chicago does in fact have a gay beach called Hollywood Gay Beach aka Kathy Osterman beach.
For full instructions and details, read more in my Gay Beach Chicago Guide.
Gay Shops in Chicago
Make sure you check out these gay shops in Chicago:
- Cowboys and Astronauts: a gay lifestyle shop with everything from clothing to styling products, accessories and décor. A really cool place with lovely owners.
- 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!
- Out of the Closet – this is a thrift store selling clothing, books & housewares; profits go to the AIDS Healthcare Foundation.
- Egoist– for all your underwear, swimwear etc needs. They also have a barber inside at the back!
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 I 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! I really felt that the whole city came together at the Chicago Pride Parade in support of the LGBTQ community.
Admission to the parade is free, and all ages are welcome.
Northhalsted Market Days
At any time of the year Northalsted 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 I have seen, I am 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. A very cute and wholesome experience.
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.
Things to do for Gay Travellers in Chicago
There is so much to do in Chicago! I stayed for 5 nights in total and was kept very busy, here are my top 6 activities in Chicago from my stay:
Legacy Walk Tour by the Legacy Project Chicago
This was an excellent and educational 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 I visited and learnt about some of these people. I did not recognise all the names straight away, but I certainly would recommend 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!
You can read more here.
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!
Architecture River Tour
I didn’t think I was interested in architecture, but this was actually a really interesting and fun tour.
The main reason I loved it was because viewing and exploring the city by river was unique and helped show me how beautiful the city really was.
I also liked the fact that the guides and staff on board had a lot of personality! Don’t just take my 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% my type of museum.
The largest and most intact T-Rex skull in the world, Egyptian tombs and bug experience had me completely sold.
For me, the dinosaur section is worth the visit alone and I would have easily stayed for hours had I 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 mynight 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!).
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
Whilst there are no exclusively gay hotels in Chicago, there are many gay friendly hotel options.
For a detailed guide, read my extensive guide to the best gay hotels in Chicago. Below is a select few hotel options.
Kimpton the Gray
This is the hotel I stayed at and I loved it. The service was excellent, the style was luxurious, trendy and modern and the location ideal for exploring the city. I also loved the fact it was a pet friendly hotel for those of you who want to bring your furry friend!
I highly recommend this hotel based on our own experience.
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
I ate so much in Chicago! Here is where I 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!
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!
I hope you found that guide useful, let me know about your experience or if you plan to visit!
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