This guide was updated on November 1, 2021
In 1893 Chicago was put in the world map as a destination of culture, architecture, and innovation as it hosted the World’s Fair: Columbian Exposition celebrating the 400th anniversary of Christopher Columbus’s arrival in the New World. This extravagant event took place just two decades after the Great Chicago Fire that left a third of the population homeless. Over the years, architect and urban designer, Daniel Burnham, who was also responsible for the famed Flatiron Building in NYC, reimagined this rough and tumbled industrial town to the modern city it is today.
Ever since, Chicago has been renowned for world-class architecture, museums, and more recently, a thriving food scene. In the May 2017 issue of Conde Nast Traveler, Chicago was named the “best restaurant city in America.” This is for good reason as it has become a foodie paradise boasting much more than deep dish pizza, hot dogs, and Italian beef sandwiches. Speaking of accolades, the culture vulture will be thrilled to hear that in 2015 Trip Advisor named the Art Institute of Chicago the best museum in the world beating out the Louvre, the Met, and the British Museum.
Chicago is not only a metropolis of food, culture, and architecture, but there’s a beach – 18 miles (29 km) of lakefront in fact. Within minutes you can go from shopping designer brands on Michigan Avenue to enjoying some fun in the sun and sand. Between downtown and the lakefront you’ll find Grant Park comprised of 319 acres (1.3 sq km) of green space to enjoy. By now you can see that a trip to the Second City is really second to none.
Table of Contents
1. General Tips
3. Airports and Transfers
4. Gay Hotels in Chicago
5. Sightseeing & Activities in Chicago
6. Tours in Chicago
7. Restaurants and Cafes in Chicago
8. Chicago Gay Bars
9. Chicago Gay Clubs & Parties
10. Chicago Gay Saunas & Cruising Bars
11. Popular Events in Chicago
12. Day Trips from Chicago
Without a doubt, any local will agree that the best time to visit is in the summer (June-September). Although Chicagoans will tout surviving blizzards and sub-zero cold snaps like a badge of honor, everyone lives for the season of rooftop happy hours, beach volleyball, and countless street and music festivals. And for the LGBT+ community, this means spending those long summer days in Boystown, the aptly named gayborhood, and Andersonville, a Swedish influenced neighborhood with plenty of LGBT+ haunts. In downtown, don’t miss the newly completed riverwalk where you can enjoy a glass of wine and a unique perspective of the Loop. It’s as if you’re in a canyon of skyscrapers alongside kayakers, yachts, and tour boats.
If you find yourself in the windy city in the winter, don’t fear! The holidays are a magical time with the whole city decked out in the season’s finest and annual traditions like the Christkindlmarket in Daley Plaza, ice skating in Millenium park, and the Macy’s storefront windows. In the dead of winter, get excited for the annual Restaurants Week that takes place in late January/early February for almost two weeks. Hundreds of restaurants in the Chicagoland area offer prix fixe meals at prices often less than one entrée on the regular dinner menu. No matter the time of year, Chicagoans will welcome you with midwest charm and hospitality.
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Chicago is home to the nation’s second-largest public transportation system operated by the Chicago Transit Authority (CTA). Servicing the Chicagoland area including 35 suburbs and the city of Chicago, you can quickly get around town using the expansive train and bus system. Between the busses and trains, you can find a way to get from point A to point B with relative ease.
Fares for rides on both the ‘L’ (trains) and busses are a fixed price per ride regardless of the destination. A Single Ride CTA ticket costs $2.25 for the ‘L’ and $2 for busses. Exact cash fares are accepted only on busses, but will cost a bit more at $2.25 per ride. CTA tickets and passes are managed by Ventra and a Single-Ride CTA ticket can be purchased at most CTA stations and include up to two transfers (i.e. train to bus and/or bus to train) within 2 hours. Another option is to purchase a $5 Ventra Card with which you can load money onto or purchase a 1-day, 3-Day, 7-Day, or 30-Day pass. For additional CTA fare and ticket prices click here. For information on the Ventra card and app to manage it, click here.
In addition to safe and reliable public transit, ridesharing apps like Lyft and Uber are very popular and the service is widely available in the city and surrounding suburbs. If you don’t already use it, Uber automatically takes care of payment with your credit card via the app and rather than taxis, they are regular people driving their personal cars. If you’ve never tried Uber you can sign up using this link to receive a $20 free credit to use on your first ride or use the code S6UQQ when registering.
If you’re more environmentally conscious or prefer pedal power, Chicago is equipped with over 200 miles (322 km) of on-street bicycle lanes. Although dedicated lanes cordoned off from the downtown traffic are increasing, most bike lanes are shared with city buses. Even the most experienced city cyclists run into trouble on the busy streets. Especially for the recreational rider, it’s recommended to stick to paths with foot traffic only like the lakefront trail and the 606. Bike rentals are aplenty through Divvy Bike with 580 stations and 5,800 bikes across Chicagoland where you can check out bicycles.
Airports and Transfers
Chicago is home to two major international airports including one of the busiest in the world, Chicago O’Hare International Airport (ORD), and the smaller yet more conveniently located Midway International Airport (MDW). The airline and various other factors will determine which airport you fly into. Both, however, are easily accessible to downtown and the rest of the city.
The easiest, most cost-effective, and often the quickest way to get from O’Hare and Midway airports to downtown is via the ‘L’ trains. The CTA Blue Line ‘L’ train runs from Chicago O’Hare on the northwest side of Chicago to downtown taking approximately 40-45 minutes and costs $5 for a Single-Ride Ventra ticket. The Blue Line runs 24 hours a day, seven days a week and all trains from O’Hare run through downtown. A taxi from O’Hare to downtown will be about $40 and take between 25 and 90 minutes depending on your exact destination and traffic.
The CTA Orange Line ‘L’ train connects Midway Airport on the southwest side of Chicago to downtown which takes about 20-25 minutes and costs $2.25 for a Single-Ride Ventra ticket. Be aware of those late-night arrivals and early morning departures as the Orange Line runs all day, every day except from about 1am to 4am Monday – Saturday and after 11pm on Sundays. During these overnight hours, alternate transportation is provided by the N62 Archer bus. A taxi from Midway to downtown will be about $25 and take between 15 and 40 minutes depending on your exact destination and traffic.
Car rentals are available at both airports, but a car is not required to enjoy the Chicagoland area and many residents rely exclusively on public transit. With that in mind, it may be wise to skip the rental car and take the CTA or other options like Uber, Lyft, and taxis. Additional transportation options to and from Chicago are the regional and cross-country Amtrak trains that arrive conveniently downtown at Chicago’s Union Station. Greyhound and Mega busses are also another option if you’re traveling to or from other US cities.
Gay Hotels in Chicago
There aren’t currently any gay hotels in Chicago, but there are many gay-friendly options. Stay in Boystown to be near the action.
Guesthouse hotel (Andersonville) – named one of the best boutique hotels in Chicago by Time Out, this family-run establishment makes you feel like a local before you even arrive with their welcome email giving you the 411 on what to do and where to go. With 25 luxe and modern one-, two-, and three-bedroom suites boasting amenities like full kitchens and laundry, you’ll be feeling like you’re at home away from home. If in-house afternoon tea at a posh getaway from the tourist sites downtown sounds like your cup of tea, the Guesthouse hotel in Andersonville will not disappoint.
The Majestic (East Lakeview) – just steps away from Boystown, Lincoln Park, and Wrigley Field, this English style boutique hotel has a fire-lit lobby and 52 rooms and suites with stately décor perfect for guests with a more refined palate. Rest assured that this classic English manor style is paired flawlessly with modern amenities such as complimentary access to a neighboring fitness facility, continental breakfast, and a fully stocked mini bar. Cheers!
Villa Toscana (Boystown) – if you want to be in the center of the action, then this charming guesthouse in the heart of Boystown is second to none! Built in 1892, this Victorian structure boasts old world European charm as each room is tastefully adorned in a different style from French to Moroccan. At the same time, the inn has all the expected modern amenities such as complimentary wireless Internet and continental self-service breakfast. The Villa can accommodate guests from a couple to a large group. However, you must reserve well in advance as it sells out quickly, especially during peak times like the Pride celebration and Market Days.
Best Western Plus Hawthorne Terrace Hotel (Boystown) – leave any preconceived notions of a standard hotel chain at home and prepare to be impressed. You’ll be invited through the quaint courtyard and meet an ivy covered brick building featuring over 80 well appointed guest rooms and suites with boutique amenities including granite bathroom counters, a Keurig coffee maker, and premium cable channels. The location can’t be beat as it’s steps away from all the bars, restaurants, and nightlife of Boystown as well as Wrigley Field and the lake.
City suites Hotel (Boystown) – just steps from the Belmont red line connecting you to downtown and a few blocks away from the nightlife of north Halstead, this modern hotel features art deco inspired decor and colorful accents. Take a closer look at the fine details such as custom-made wood headboards, wardrobes, and desks as well as the fully stocked mini bar and separate sitting rooms in the suites. From the fun and friendly rooms with ample amenities to the superb location, City Suites Hotel is an ideal pick for a weekend in the windy city.
Chicago Getaway Hostel (Lincoln Park) – located in Chicago’s Lincoln Park neighborhood, Chicago Getaway Hostel claims to reinvent the hostel experience for the modern wanderlust. Imagine matching hotel-style service with great deals in an ideal location. Check out the amenities such as free WiFi, communal kitchen, daily breakfast and free coffee, and weekly social events and guest lockers. You have a choice of private rooms with shared baths, private rooms with ensuite baths, and bunkrooms for four to 12 people. For the budget traveler, this clean and modern hostel will fit the bill without breaking the bank.
Wrigley Hostel (Wrigley) – let your inner baseball fan out and stay in the heart of the action at this Wrigleyville hostel. There’s no better place to meet new people and take part in daily social events such as bar crawls, movie nights, and comedy nights. Choose accommodations from a private room to an eight-bed dorm-style room with bright colors and hardwood floors. Enjoy all the amenities such as secure guest lockers, free Wifi, and complimentary breakfast. Whip up your favorite dish in the fully equipped kitchen and lounge on the outdoor patio and grill. If the weather isn’t ideal hang out in the game room or check out the latest happenings in the computer room and library.
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Sightseeing & Activities in Chicago
Chicago is one of those cities you keep coming back to as there’s always something more to see and do. This is especially true with its diverse neighborhoods that feature food and culture from around the world. A few of the must-see sights sitting at the top of any guidebook are the Willis Tower Skydeck, Navy Pier, The Art Institute of Chicago, Millennium Park, and an architecture boat cruise. Although you’ll encounter the touristy crowds, they are rights of passage and will not disappoint on a first-time trip to Chicago.
Art Institute of Chicago – named the best museum in the world by Trip Advisor in 2015, the collections at the art institute contain about 300,000 masterpieces with temporary exhibitions opening several times throughout the year. Don’t miss iconic works such as The Bedroom by Vincent Van Gogh, A Sunday on the Island of La Grande Jatte by George Seurat, American Gothic by Grant Wood, Nighthawks by Edward Hopper, and The Old Guitarist by Pablo Picasso.
Willis Tower Skydeck – originally named the Sears Tower when it was built in 1973 (as it’s still referred to by many locals), this skyscraper stood as the tallest building in the world for 25 years and is now the second tallest building in the western hemisphere. All the way up on the 103rd floor, the Skydeck features retractable glass balconies that allow you to stand on a four-foot glass ledge looking down to the street 1,353 feet (412 m) below. Book tour →
Millennium Park – built over the sight of an old rail yard, Millennium park is home to one of Chicago’s most popular sights, a 66-foot (20 m) tall stainless steel sculpture by Anish Kapoor called Cloud Gate. It has been lovingly nicknamed “the bean” due to its likeness to a giant kidney bean. In the summer, enjoy live music and performances on the lawn of the Jay Pritzker Pavilion and in the winter strap on a pair of skates at the McCormick Tribune Ice Rink, a holiday tradition for many.
Chicago Riverwalk – if you’re looking to venture away from the crowds of Michigan Avenue and State Street, take a stroll along the newly renovated riverwalk where locals and tourists mix and mingle. Stretching from Lake and Wacker to Lake Michigan, the uninterrupted path is dotted with green spaces, public art, and a perspective of the city you can’t get anywhere else. Here you can enjoy small bites and sips at one of the many cafes and people watch as families, runners, and even yachts pass by.
Broadway in Chicago – don’t let the name Broadway in Chicago fool you into thinking that the Chicago theater scene isn’t booming with talent and much cheaper ticket prices than its Big Apple cousin. A peek inside some of these historic theaters is worth the ticket alone. A few noteworthy ones include the Chicago Theater, Oriental Theater, and Auditorium Theater.
Second City & Improv – Chicago is also home to many small theater spaces hosting improv comedy shows and the most famous is Second City. This Chicago institution produced the likes of Tina Fey, Steve Carell, and Joan Rivers to name a few. Comedy and improv shows are a plenty and can cost just a few dollars per ticket. The raw talent is truly impressive.
Museum Campus – so just how do people get those fab panoramic skyline views of the city without walking on water? Head over to the Adler Planetarium for some of the most Instagram-worthy cityscape snaps. While you’re there, explore the museum campus that is a giant pedestrian-friendly park consisting of the Adler Planetarium, the John G Shedd Aquarium, and the Field Museum.
Navy Pier – one of the most visited sights in the Midwest and a former World War II training center, Navy Pier is home to some of Chicago’s most iconic seafaring craft such as tall ship “Windy,” entertainment cruise ships, and Shoreline Sightseeing cruises. Every Wednesday and Saturday nights during the summer enjoy a spectacular fireworks display. Hop on the newly constructed Centennial Wheel taking you up 200 feet with 360-degree views of the city. If heights aren’t your thing, take in a flick at the iMax movie theater or enjoy a performance at the Chicago Shakespeare Theater.
If you’re planning to visit many sights and attractions during your stay, it might be worth it to check out a tourist card like the Chicago Explorer Pass that allows you to enter several sights at a fixed price. Buy Pass →
Tours in Chicago
Chicago is a perfect place to explore by foot, boat, bicycle, and even Segway! Chalked full of breathtaking architecture and compelling history, you’ll definitely want to take advantage of a tour or two to dive deeper into this city’s vibrant past, marvel at the present, and wonder about the future. Walk aboard an architecture boat cruise, follow a docent down the the grid-like streets, or cycle on the lakeshore. Start your journey at the Chicago Architecture Foundation located at 111 E. Wacker Drive. Here you’ll discover exhibits, programming, and tour options highlighting Chicago’s world-class architecture.
Architecture Boat Tour – one of the best ways to experience the rich architectural landscape of the city is by boat, cruising on the Chicago River. This is a must-do in Chicago as tourists and locals alike can be found aboard these vessels to learn about the city and admire the stunning views. There are several tour companies and each offer different types of cruises like to see the sunset, fireworks, or focus on a specific geography or topic. Most tours are led by very knowledgeable guides who will share history, fun trivia, and point out the best photo ops. Book tour →
West Loop Food Tour – one way to eat your way through the Windy City is by joining a food tour. Although there are many that take place downtown targeted at tourists, venture to one of the neighborhoods for a more authentic flavor. Check out tours in places like Pilsen, Chinatown, the West Loop and Little Italy for local eats and restaurants that are off the beaten path. These are an ideal way to discover a new part of the city while filling your belly with tasty eats. Book tour →
Walking, Biking, Bus Tours – there are so many ways to roam around while discovering hidden gems. Chicago is a very pedestrian-friendly city, so walking tours are very common and sometimes the best way to sightsee at your own pace. If cruising on two wheels is more your style, bike tours are the way to go. Like many other cities, the big red double-decker buses are always an option. Pick your preference and get out there to learn some neat history and enjoy one of the country’s first modern cities. Book tour →
Restaurants and Cafes in Chicago
Chicago’s food scene is booming and the variety of innovative cuisine is a reflection of the city’s diverse and culturally rich neighborhoods. First, go ahead and stuff your face with the obligatory deep dish pizza, dipped Italian beef sandwich, and a hotdog “dragged through the garden.” Then make your way to some of these trendy and LGBT-friendly eateries. From food truck empanadas to diner vegan milkshakes, here’s a taste of our favorites.
West Randolph – often referred to as restaurant row, this stretch of Randolph just west of the expressway is a foodie mecca boasting some of the hottest new restaurants and bars. A few standouts include Au Cheval for its famed burger, the Aviary to sip swanky cocktails, and Top Chef Stephanie Izard’s Girl & The Goat. Beware that some of these spots can book up months in advance, yet sometimes you can snag an open table during non-peak hours.
Food Trucks – the food truck craze has finally made its way to Chicago. If you’re trying to pin down a specific eatery, many will share location updates on social media. Popular downtown hangouts for these kitchens on wheels are Clark/Monroe, Adams/Wacker, and Daley Plaza. A few staples are Beavers Coffee and Donuts, 5411 Empanadas, and Harold’s Chicken. If you ever miss one, remember that most have brick-and-mortar locations you can visit, too.
The Chicago Diner – having been graced by the presence of Lady Gaga, this Chicago eatery has been “Meat free since 83.” It’s an oasis for those with dietary restrictions as there are countless vegetarian, vegan, and gluten-free plates. Even carnivores will be floored by the meat-free Radical Reuben and the award-winning vegan milkshake to wash it down. The original location is in Lakeview on Halsted (Boystown) and the newest is in Logan Square.
Boystown – the gayborhood is better known for dance floors and disco balls than a killer food scene. However, there are still some great spots to enjoy a meal whether it’s a chill weeknight or a night out on the town. From brunch to craft cocktails, Wood is named after its wood-fired oven offering American small plates. A popular no-frills hangout is DS Tequila Co. serving up burgers, Tex-Mex and, of course, Tequila drinks on the patio.
Lakeview – these honorable mentions are just a short walk from the main Boystwon strip in the Lakeview neighborhood. One of the first vegetarian and vegan-friendly restaurants in the city, Pick Me Up Cafe is ideal for lunch or a late night bite with a cozy and eclectic atmosphere. Cocktails and brunch sum up Pork & Park Bistro, a tavern and lounge featuring global American plates with an extensive bar list. Satiate your sweet tooth at Bobtail Ice Cream, an old-school ice cream parlor scooping up homemade ice cream, sundaes, shakes, and coffee.
Andersonville – venture a few “L” stops north of Lakeview and you’ll find another LGBT-friendly community. Start with brunch at m.henry where traditional dishes get a farm-fresh twist like the dandelion, shallot, and leek omelette. Additionally, the menu has tasty gluten-free, vegetarian, and vegan options. Housed in a vintage art deco building, Tweet is another popular brunch (and lunch) spot with an artsy flair. American comfort food takes on gluten-free and plant-based variations at this cash-only gem.
Chicago Gay Bars
Sidetrack – show tunes and adult slushies, what’s not to like? This spacious video bar has numerous bar areas and spots to chat and mingle. Themed nights often feature drag shows and music videos on the enormous screens. You’ll find a diverse crowd here and the rooftop bar and patio is a must-see in the summer.
Elixir – with locations in both Boystown and Andersonville, this fancy cocktail bar will fit the bill when you’re craving something more sophisticated than a vodka soda. Enjoy carefully crafted drinks like a signature martini and weekly specials at this trendy cocktail bar.
Roscoe’s – one of the best-known and most popular Chicago gay bars, Roscoe’s Tavern was established in 1987. It really has the best of both worlds. There’s a neighborhood bar vibe in the front and a large dance floor in the back half. Check their calendar for regular drag shows and special events.
Kit Kat Lounge & Supper Club – embrace your inner diva with the Kit Kat Divas at the nightly shows that run every 20 minutes. Peruse a martini and cocktail list of over 200 items while savoring upscale contemporary cuisine at this entertainment hot spot.
Second Story Bar – one of the few gay bars downtown, this is an unpretentious, old-school bar with a disco ball. The divey digs draw a mixed crowd of travelers and locals looking for a libation in a comfortable and friendly atmosphere. Just remember it’s cash-only.
Chicago Gay Clubs & Parties
Scarlet – vintage-inspired bar and lounge with a club atmosphere, themed nights, and special events. The DJs and drink specials attract a 20-something crowd ready to dance the night away.
Splash – modern styled space with two side bars and a dance floor touting yet another bar all with attractive bartenders. Enjoy EDM beats from the DJ, colorful lights, and reasonably priced drinks at this new Boystown hangout.
Late Night Clubs – as the lights for last call switch on, you’ll want to make a beeline for the door and head over to one of these late-night clubs open until 4 or 5am on the weekend. Hydrate is in the heart of Boystown and has a contemporary vibe featuring a lineup of DJs and themed nights. Berlin is a no-attitude nightclub featuring alternative electronic music that draws an eclectic crowd. Try to head over earlier in the night to avoid long lines at the door.
Chicago Gay Saunas & Cruising Bars
Steamworks Baths – a towels-optional private men’s gym, sauna, and bath house. Memberships start at $8 and the facility has many amenities including private rooms, slings, whirlpool, and showers for gay and bi men looking for a playful time.
Popular Events in Chicago
Midsommar Fest – traditionally a celebration of the summer solstice, this LGBT-friendly street-festival is a tribute to Andersonville’s Swedish heritage. Usually landing on the second weekend of June, enjoy two days and three nights of live music, delicious food, and activities for all ages. Festivities are on Clark Street stretching from Foster to Catalpa, and residents and local businesses make this a very inclusive and friendly atmosphere for all.
Chicago Pride – the main event is the pride parade that usually takes place on the last Sunday of June with a route stretching from Montrose to Diversey on the northside. The Saturday morning before is the annual Proud to Run 10k run and 5k walk benefiting several community organizations. However, festivities really begin the weekend before the parade as the pride street festival kicks off the week-long celebration. Pride-related events can be found throughout the city during the entire month of June. Even downtown and in the financial district businesses and large institutions proudly fly the rainbow flag.
Lollapalooza Music Festival – an annual four-day music festival, fans come out to see almost 100 performing artists. It takes place in Grant Park the first week of August to delight throngs of music fanatics. Although there are countless smaller music festivals throughout the summer, this is by far the largest with the best-known headliners. Tickets are tough to get and your best bet is to buy through a reseller.
Northhalsted Market Days – this is the largest outdoor street festival in the Midwest with attendance of over 200,000. It covers six block of North Halsted right in the center of boystown with five stages and a non-stop lineup of live music, food, and craft vendors. Think of this as an unofficial pride part II on one of the first weekends of August. Attendees aren’t afraid to express themselves with colorful colorful outfits and the drag queens are fierce.
Day Trips from Chicago
Lake Geneva, WI – about a two-hour drive northwest of the city is one of the most popular getaways for urban dwellers. Stroll up and down the quaint main street boutiques and stop for a bite at a restaurant or cafe. Chill out on the beach or get out on the lake for boating and water sports. Take a cruise to marvel at the stunning lakefront mansions or check into a spa for some pampering. From spring to fall, this town will give you all the vacation vibes without the jet lag.
Oak Park, IL – not only is Chicago an architectural gem, but the nearby suburb of Oak Park has one of the largest concentrations of Frank Lloyd Wright homes in the country. In addition to being a picturesque town in its own right, take advantage of the many walking and bicycle tours of these Prairie-style homes just a short “L” ride from downtown.
Starved Rock State Park – situated in Oglesby, IL on the banks of the Illinois River, Starved Rock is about a two-hour drive southwest of Chicago. The state park is for the outdoorsman who enjoys camping and hiking. Although most of the midwest is flat grasslands, here you can explore waterfalls and unique rock formations. One of the best times to visit is in the autumn when the foliage lights up in colorful hues of yellow, orange, and red.