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 mecca 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. Literally within minutes you can go from shopping designer brands on Michigan Avenue to enjoying some fun in the sun and sand. Between the 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.
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.
If you find yourself in the windy city in the winter, don’t fear! The annual Restaurants Week takes place in late January/early February with almost two weeks and hundreds of restaurants in the Chicagoland area offering prix fixe meals at prices often less than one entrée on the regular menu.
A stroll along the newly completed riverwalk will provide a unique perspective as if you’re in an urban Canyon alongside kayakers, yachts, and tour boats.
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. You can use the trip planner online for exact directions and timing or browse the metro rail and bus transit maps for a custom adventure.
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….(http://www.transitchicago.com/fares/). For information on the Ventra card and app to manage it….(https://www.ventrachicago.com/)
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 many suburbs. If you don’t already use it, Uber automatically takes care of payment with your credit card via the app and rather than taxi’s 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 busses. 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 a plenty through Divvy Bike with 580 stations and 5,800 bikes across Chicagoland where you can checkout and check back in 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). Depending on 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 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, everyday 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 rely on 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 & Gay Friendly Accommodations in Chicago
Guesthouse hotel (Andersonville) http://www.theguesthousehotel.com/
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) http://majestic-chicago.com/
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) http://thevillatoscana.com/
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 anyone 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) http://www.hawthorneterrace.com/#gref
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 nightlight of Boystown as well as Wrigley Field and the lake.
City suites Hotel (Boystown) http://chicagocitysuites.com/
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) http://www.getawayhostel.com/
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) https://www.wrigleyhostel.com/
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 from a private room to an 8-bed dorm style room with bight 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.
There are many sites for apartment rentals in Chicago, with AirBnB probably being one of the most popular. Prices are generally comparable to budget hotels, especially if you’re willing to get a room in a shared apartment.
There are even a few LGBT-oriented booking sites like misterb&b with listings from gay hosts for gay guests where you can either rent a whole apartment or a private room in a shared apartment. Understanding DC’s gay scene is much more easily done with the help of a local and apartment sharing is one of the best ways to meet someone living in the city who knows how things work, where and when are the best nights to go out, and what places to eat at and which to avoid.
Sightseeing & Activities + Things To Do 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 that will at the top of any guide book 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 works with temporary exhibitions opening several times throughout the year. Don’t miss iconic works such as The Bedroom by Vincet 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 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.
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 steal sculpture by Anish Kapoor called Clout 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.
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 peak 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.
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.
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 show. 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 CityPASS that allows you to enter several sights at a fixed price.
Tours in Chicago
- CAF Boat Tour
- Chicago Ambassador free tour
Restaurants and Cafes in Chicago
- West Randolph Restaurants
- DS Tequila Co.
- Bobtail Ice Cream
- Svea in Andrsonville
- Foodhall in Loop?
- Wood Restaurant – bar & food
- Brunch spots
- Taverna 750
Chicago Gay Bars and Lounges
- Sidetrack – show tunes & slushies
- Elixir – Fancy cocktails
- Roscoe’s – dance floor & drag shows
- Second Story Bar in Loop
- Progess Bar
- The Lucky Horseshoe Lounge
Chicago Gay Clubs & Parties
- 5am bars – Berlin & Hydrate Night Club
- Spin Night Club
Cruising in Chicago & Men Only
Popular Events in Chicago
- Pride Festival & Parade http://chicagopride.gopride.com/
- Lollapalooza https://www.lollapalooza.com/
- Market Days https://www.northalsted.com/marketdays/
Day Trips from Chicago
- Lake Geneva http://www.visitlakegeneva.com/
- Oak Park FLW Houses http://flwright.org/tours
- Starved Rock State Park http://www.starvedrockstatepark.org/