Weekend: Chicago

Chicago is one of my favorite cities to visit—especially in the summer. From its lively and diverse neighborhoods to the buzzing lakefront scene and endless street festivals—including several LGBTQ-focused ones—it’s a city that knows how to make the most of the season.

I’ve been lucky to experience Chicago in spring, summer, and fall, and while every season has its charm, summer is where the city truly shines. Whether you’re into LGBTQ events, outdoor concerts, foodie experiences, or simply strolling along the Lakefront Trail, there’s something for every kind of traveler.

My connection to the city runs a little deeper—my husband lived in Chicago for six years, so returning means reconnecting with friends and blending local vibes with tourist favorites. It’s the perfect balance of community, culture, and fun.

Post updated 5/2025.

Know Before You Go

I’ve had friends and family ask about safety in Chicago. The city might have a reputation, but is Chicago safe, you ask? I always respond yes.

Sure, you can be in the wrong place at the wrong time anywhere, but I’ve found Chicago to be clean, welcoming, and safe at all hours. Your experience (or comfort level) may vary. Be aware of your surroundings, don’t do stupid stuff, and chances are you’ll be just fine. But here are some other tips:

• Transit is cheap, easy, and (generally) fast, including from both major airports (more on that below). You’ll save a ton of coin compared to a taxi or Lyft. Oh, and at least based on my experience at O’Hare, skip the line of folks getting a fare card. Just tap your credit card or Apple/Google pay at the fare gate en route to the platform.
• Chicago is a BIG city with a lot going on. Give yourself extra time to get to and from places. Oh, and you’re 100% not going to do it all while you’re there. There’s way too much of everything and it’s all too spread out to do it all. So identify your priorities and if you make it to more than that, awesome!
• Street fairs and events! Many (most?) of Chicago’s 77 formally-recognized neighborhoods host street fairs, and the ones I’ve attended are worth the trip. Market Days (or, more formally, Northalsted Market Days in Boystown) is appropriately gay, full of music, food, and entertainment, and maybe more fun than pride. Andersonville Midsomerfest is a little less gay but just as fun. Don’t miss 80s cover band Sixteen Candles at each of these.
• And then there’s International Mr. Leather over Memorial Day, which brings thousands of LGBTQ folks to Chicago for a weekend or more. I’ve had epic fun at each of these.
• Your experience might be different, but please don’t call it shy-town

Getting There

A great thing about visiting Chicago is how easy it is to get there directly—no matter where you’re coming from.

If you’re coming by air, Chicago is home to two major airports: O’Hare International Airport (ORD) and Midway International Airport (MDW). O’Hare is a global hub with extensive domestic and international connections, while Midway is smaller and your primary destination if you’re on Southwest. This probably won’t dictate your flight choices, but lounge lizards will probably prefer O’Hare (and the lounge is nice when your flight there is inevitably delayed). There’s a good guide here. Both airports are connected to downtown via the CTA “L” trains—the Blue Line from O’Hare and the Orange Line from Midway.

If you’re coming from nearby cities, it’s also easy to arrive by train, including recently improved service from Milwaukee, as well as trains from St. Louis and Detroit.

And if you’re driving into Chicago … well it’s doable but can come with traffic and parking challenges (and expenses), especially downtown. If you’re road-tripping, consider staying in a neighborhood with easier street parking and using public transit or rideshares to explore the city. Chicago’s grid layout and extensive public transportation make getting around without a car very manageable.

LGBTQ Safety

Chicago is widely considered one of the most LGBTQ-friendly cities in the U.S., with vibrant queer neighborhoods like Boystown (now often referred to as Northalsted) and Andersonville. And it tops a list of safest U.S. cities for LGBTQ travelers, according to short-term rental service misterb&b (note that their list is weighted toward cities on their site most booked and with the most hosts). I’ve always found it to feel inclusive across the city as well. Overall, I think LGBTQ travelers can feel safe and welcome in Chicago, particularly in areas where queer culture is celebrated, supported, and visible year-round.

All of the things above being said, as with anywhere, it’s still smart to stay aware of your surroundings—especially late at night or outside of the more central neighborhoods.

Sightseeing Highlights

My suggestions below are an amalgamation of about 20 years of trips to Chicago. Do not attempt to do this all in a weekend! There’s so much to do in Chicago that you should 100% come back and do more of it next time. But here are a number of ideas for your itinerary

• Not just for your Instagram, but also for your Instagram: Millenium Park and Cloud Gate (aka: the Bean). Let’s be real here – if you’re looking for an iconic Chicago photo, the Bean definitely one of them. But the park is much more than just the Bean. Check out the rest of the sculptures, the water feature-slash-multimedia art exhibit, maybe a concert, you name it. The park is beautiful and it’s a wonderful place to send 30 minutes or 5 hours.
• Chicago’s river architecture tour: It’s so nice, I’ve done it twice. And I would (and will) do it again. Touristy? Perhaps. But I think it’s one of the best things to do in Chicago—even more so if you like architecture. It’s essentially the greatest hits of architecture plus history plus culture all in one. There are several tour operators, but I haven’t done them frequently enough or back-to-back that I have a favorite.
• Lake Michigan’s waterfront. Yeah, I realize this encompasses a lot. Chicagoans might not have even spent time at most of it because it’s a lot. But if you’re in Chicago in the summer, check it out. Maybe do a stroll or an afternoon on Concrete Beach (aka: Oak Street Beach). Maybe have a drink or snack at Sandbox Beach Cafe. Maybe take a photo on the lakeshore with Chicago’s skyline in the background, as I did. I mean, you could even potentially swim in the lake. I guess. Oh, and if you’re up for the gay scene, don’t miss Hollywood Beach (aka: Osterman Beach) on sunny summer days.
• The John Hancock and Willis (formerly known as Sears) Tower. Architecture fans will no doubt nerd out on Skidmore Owings & Merrill history, but even non-fans will appreciate the views from the trippy glass pop-out in Willis Tower (see photo below) and the CloudBar on the 94th floor of the Hancock building (now known as CloudBar at 360 Chicago). You’ll pay for the views, but it’s still pretty awesome.
• The city’s rejuvenation of the Chicago Riverwalk has made it a wonderful place for locals and visitors alike to stroll, grab a beer, people watch, or—as I noticed on our last trip—take your wedding engagement photos. Dozens of restaurants, tap rooms, and cocktail bars have popped up along the nicely-landscaped walkway, making it a great place to wander and snack your way through an afternoon.
• It’s been several years since I caught a show at Second City, but it’s something that’s always on my “should do” again list. Comedy geniuses for decades have gotten their start here and it’s a great place for a side-splitting good time.
• Last, but not least, the 606 Trail is a relatively new addition to Chicago. To be fair, I haven’t yet checked it out (see above comment about too much time with friends to do everything), but it’s on my shortest list of things yet to do. It’s awesome to see cities transform their under-utilized infrastructure to create recreation spaces and this is a great example that appears to be trying to one-up New York’s Highline and Atlanta’s Beltline. If you ask me, there are no losers in this contest.

Eating and Drinking

Confession: this section is not going to do justice to the variety or quality of Chicago’s food scene. Most of my trips to Chicago have been centered on spending time with friends or exploring street festivals, with less focus on great food. That said, I’ve still scored a number of highlights.

• Girl & the Goat is on a short list of Top Chef-alum restaurants I’ve eaten at, and Stephanie Izard’s cuisine is everything I wanted it to be. Fun. Delicious. Inventive. Wonderful.
• The Wiener’s Circle is at the polar opposite end of the culinary spectrum, but is also an experience. You’ll probably get yelled at and you’re gonna eat a hot dog. But it’s also fun, delicious, and wonderful. And probably best enjoyed after a beer or two.
• I don’t know if you’ve heard, but Chicago is a pizza town. And for good reason. The hubby and I have ordered, brought home, or otherwise consumed a lot of Giordano’s deep dish deliciousness. And on our most recent trip, we discovered Dough Bros (open late!) serving up really, really good New York and Detroit-style pizza by the pie or the slice. Count your memories, not your calories.
• If you’re downtown, don’t let the name fool you, The Dearborn Tavern is a wonderful upscale spot for brunch (or presumably other meals too). Their self-proclaimed “Chicago’s best fish and chips” are, in fact delicious, as are the chicken and waffles with just a little bit of heat in the syrup.
• Big Chicks and sister restaurant Tweet serve up fun food and drink (Big Chicks for dinner and weekend brunch; Tweet for breakfast). They regularly sponsor local LGBTQ sports teams (which has earned them a place of the Chicago LGBT Hall of Fame), so on summer weekends, chances are good you’ll find more than a few folks hanging out post game. They don’t take reservations or credit cards, though, so plan to wait a bit for a table and bring cash.
• On N. Halsted, Roscoe’s actually has pretty good bar food, and Drew’s is a decent, if not extraordinary, spot for breakfast or lunch before hitting the bars up the street.
• Or McDonalds. Hear me out: international food nerds (myself included) may be interested in knowing that much of McD’s global menu is available at the restaurant adjacent to their headquarters and Hamburger University.
• And while I can’t vouch for the content within, there’s a list of all the restaurants featured in The Bear which sounds like a great reason to explore and eat your way through town if you’re in the mood for that.

Nightlife

It’s been said that the worst decisions make the best memories. And we’ve made some great memories in Chicago. 😂

Boystown (N. Halsted Avenue) is the heart of Chicago’s gay nightlife and also home for Market Days in August, which is great fun. Andersonville Days (Midsommer fest) is also an awesome festival to check out.

• Sidetrack is such a fun spot to spend an afternoon or evening, and especially on their roof deck in the summer. I wouldn’t consider myself a showtunes aficionado, but Showtunes Sundays here are just too much fun.
• Roscoes is a great spot to have fun, drink and dance (and, as noted above, some bar food, if you need it).
• Hydrate holds a special place for me, not just because it’s a great Chicago club, but also because they fully embraced virtual hangouts during COVID and helped get me through the stay-at-home phase of the pandemic.
• North End is a favorite hangout for sports teams after their games. Come for a beer, some darts, or whatever suits your mood. New windows at the front mean the bar opens up to the street on warm days.
• One of the few gay bars in downtown, The Second Story is a great place at happy hour time. It’s small and cash only, but bartenders are friendly and the drinks are cheap(ish) and strong.
• Cell Block and Jackhammer are a bit grittier and seedier and are fun holdouts of the genre, in contrast to Eagle bars hosting drag shows (nothing wrong with that, but there’s a time and a place…). The appropriately named Hole, downstairs at Jackhammer, gets busy with all sorts of lubed up debauchery, especially on event weekends. Check their page for goings-on and be sure to note that some events have pretty rigid dress codes.

Lodging

I love Chicago, but here’s the one spot that the city really lets me down. Don’t get me wrong—there are so any places to rest your head in Chicago. They just aren’t where I wish they were.

Want to stay near Wrigley Field or Boystown? Lower your expectations and open your wallet. You can choose from the maybe-cute-but-spendy Hotel Versey, an overpriced Best Western, a few hostels, or just hand over your entire retirement account for a night at the Hotel Zachary.

Considering the above challenges, I usually stay downtown. L trains are close and frequent enough to get you to where you want to go, and hotel rates aren’t as ridiculous as those in the Wrigley/Boystown area.

On our most recent trip, the Hampton Inn Downtown (the one on Wacker—there’s another on the other side of the River) was a decent price, but frankly was disappointing, despite a convenient location. The Citizen M next door looked really nice from what I could see in their windows from mine. 😆

There’s yet another Hilton Garden Inn across from Sears—er, Willis—Tower that seemed quite new when we stayed there in 2024. I suppose that’s to say, check recent reviews but there are lots of options downtown.

The above notes about variety and selection also track for Marriott properties, if that’s your thing (I’m a fan of their Moxy hotels). The Wade Hotel on Lakeshore is also a beautiful location (and views, depending on which room you get). I’d stayed there back in 2001 when it had just opened as the W Hotel, and I suspect it’s quite nice now given the 2025 rebrand, becoming The Wade. And if you’re inclined toward Hyatts—or perhaps are in town on a convention, the Hyatt Regency is well located and rooms overlooking the River have beautiful views.

Attendees of recent IML events will also know the Congress Plaza Hotel. The location across from Maggie Daly Park is convenient, but the hotel itself is pretty sad and worn. Unless you’re headed to Chicago for IML and really want to be at the host hotel, I’d recommend other nearby options.

Speaking of options, plenty of other options are available in downtown, which keeps competition high and prices generally moderate. Which is to say: Chicago is a good city to do some shopping before you book.