One of the very best times to experience Chicago is during June — Pride month. The parade, welcoming upwards of 1 million people, takes place the last Sunday of June, but throughout the month there are seriously fierce events across the city’s queer enclaves, in Boystown, Andersonville, Uptown and Rogers Park.
Fewer places warm up as delightfully as Chicago in early summer, especially with miles of sandy beaches, loads of outdoor dining and activities along the lakefront. With so much happening during the day, it gives you a chance to take off your tank, soak up the rays and show your pride.
Here’s what you need to know to make the most of pride in Chicago.
1. Meet and Greet Local Pride Guys
Whether you’re hitting one of the many Pride-related events, hanging out at Hollywood Beach, cruising Boystown’s Halsted strip or going for a run or bike ride on the Lakefront, LGBTQers seem to take over the city. And during the parade itself, on June 24, sexy floats whip the celebrating throngs into a frenzy. This is the unofficial start of summer in Chicago, and things get hot. Fast.
2. Book a Room on the North Side
- Hotel Zachary: Set in the shadow of Wrigley Field, this new 175-room hotel opened this spring and boasts a fantastically designed lobby lounge with a large four-sided bar and a sprawling outdoor deck facing the Friendly Confines (even if you’re more into day drinking than baseball). If that wasn’t enough, the property includes a variety of restaurants, including Big Star (tacos), Mordecai (a cocktail-focused New American restaurant), West Town Bakery & Tap, Smoke Daddy barbecue and the forthcoming Dutch & Doc’s, from the Boka Restaurant Group, the team behind Girl & the Goat, Somerset and GT Fish & Oyster. And, yes, each spot has outdoor space perfect for day-drinking in the sun.
- Best Western Plus Hawthorne Terrace: You may not think of a Best Western as your go-to spot, but this property, in the heart of Boystown, has a boutique hotel feel with its leafy entrance, apartment-like rooms, daily breakfast with huge Ann Sather cinnamon rolls and a tree-covered garden terrace, where you can read the newspapers with your morning coffee as you watch the rainbow festooned boys sashay on Broadway.
- The Guesthouse Hotel: If you want to be close to the action, but not in the middle of it, check out this chic and quaint Andersonville property. Stepping into the space, you feel like you walked into your friend’s really nice pet-friendly home, with leather chairs and marble-topped counters in the common areas, plush bedding and an open-air rooftop with stunning views. Need a rub down? Pop by Revive Spa next door.
3. Never Get Hangry
Every good gay knows how to brunch like the best of us, but there’s more to eat than just an egg-white omelet and bottomless mimosas. Keep your taste buds satisfied in the gayborhoods’ best spots during Pride month.
- Big Jones: Some of the best Southern cooking north of the Mason-Dixon, with an extensive bourbon collection.
- Little Bad Wolf: Can’t decide if you’re hungry for burgers, bao, mussels or tacos? It has it all — and you can sit inside or out on the sidewalk cafe and enjoy a summer breeze.
- Middle East Bakery & Grocery: Deliciously authentic falafel, shawarma, and kebabs — need we say more? We love this inexpensive spot where you can grab your food and stroll Clark Street in Andersonville or take it to a nearby park for a DIY al fresco picnic. (Pro tip: Grab a bottle of chilled rosé from Pastoral up the street.)
- Wood: An upscale yet approachable mainstay on Halsted, with rotating seasonal fare and fantastic cocktails. The sidewalk patio just off Halsted is a perfect place for people watching while you sip your mimosas at brunch.
- Las Mananitas: As if the food weren’t good enough, the potent pitchers of margaritas are really why you’re here. And while you might have to wait for a little while, the quaint umbrella- and tree-covered side patio is where you want to be.
- Crisp: Korean chicken wings that will blow your mind but not your wallet.
- 5411 Empanadas: Doughy pockets of Argentine deliciousness filled with a variety of meats, vegetables, and even sweets.
4. Make the most of the parade
A few years ago, the city and Pride organizers adjusted the parade route. It used to loop around Boystown, and you could watch both on Broadway and Halsted.
Now the parade stretches farther north into Uptown and down into Lakeview, along Broadway and Halsted. While the overly eager will crowd into the space around Halstead and Roscoe, those who want a little more breathing room will stay a bit farther north of Addison and still get the same energy without being mashed into a mosh pit. (Pro tips: Wear sunscreen. Hydrate, and limit yourself to a beer or two. It’s a marathon, not a sprint, honey.)
5. The rest of the fest
Pride isn’t just about the parade on June 24. A host of outdoor events that usually start during the day and keep going strong into the night will take place during the month. You’ll want to check them out.
- Midsommarfest (June 8-10), in Andersonville, is often considered the kick off to Chicago’s Pride events. Hit the street, listen to the bands and pop into the bars and restaurants. Then make some new friends and go to parties after.
- Pride Fest (June 16-17): The weekend before the parade, Pride Fest shuts down Halsted Street in Boystown for a raucous street festival with 100,000 of your closest friends. This year’s performers include Mýa, Belinda Carlisle, and Brian Justin Crum.
- Proud to Run (June 23): Sign up for the 37th annual 10K and 5K run, set at beautiful Montrose Harbor, to help raise funds for Chicago’s LGBTQ community — and show the other 2,000 runners why you hit the gym 5x a week.
- Back Lot Bash (June 22-24): Meet up with other ladies at one of Pride weekend’s most popular lesbian gatherings, with music, food, dancing and more.
6. Dress for summertime success
A world-class city, Chicago has world-class shopping, but also plenty of local independent shops where you can grab a new square cut for the beach, a super cute rainbow tank to stroll the street fest or a new T or polo to dress it up a tad for dinner. You could pop down to Michigan Avenue and Oak Street — even on Southport in Lakeview — to find global retailers like Uniqlo, J.Crew and Barneys New York. But pop into the neighborhoods for the local fare with distinctive items.
- Cowboys and Astronauts: This new Andersonville boutique offers brands not found elsewhere in Chicago. You can find denim, shorts, great caps, housewares and more.
- Cram: Whether you need cute new undies, a skimpy bathing suit or a fitted floral Ben Sherman top, CRAM (the owner’s name backward) has you covered. And it’s right in Boystown.
- Mildblend Supply Co.: Quality denim, leather shoes and sleek outerwear are the main draw at this super-cool Wicker Park shop, but you can also pick up cool sunglasses, bags, form-fitting shirts and more.