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Hotels in Boystown

157 Travelers rated Boystown highly for Lakes and Dining

1 Room
2 Adults
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Feb 23 - Feb 25
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Mar 2 - Mar 4

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Proud and ready to parade in Boystown, Chicago

If you're heading to the Windy City for its fabulous nightlife, Boystown is the place to go. Known as Chicago's LGBT community, hundreds of thousands descend upon the neighborhood every year for one of the country's largest pride festivals. Boystown promotes equality and values non-discriminatory fun for guests to join in with.

This lively area is situated directly east of Wrigleyville and is a convenient location for baseball fans who only have to cross North Sheffield Avenue to catch a Cubs game at Wrigley Field.

Things to see
Oracle Theatre

This is a great place to experience some of the city's best live theatre, with productions presented free of charge. Running successfully since 2005, it presents art, dance, film and performance art. The theatre's inventive set designs add a final element of intrigue.

Wrigley Rooftops

Baseball fans will surely know about the Wrigley Rooftops, where fans sit on the tops of houses located across the street from the ballpark to watch the games. The ones beyond the right field fence are actually located in Boystown. These vantage points are as historic as the stadium itself and Cubs fans have watched games from there since 1914, the same year that Wrigley Field opened.

Center on Halsted

The Midwest's largest LGBT community center welcomes hundreds of people every day who take advantage of its public programs. If you are a sports fan, make sure to browse the National Gay and Lesbian Sports Hall of Fame, which has been located here since 2013. Note that everyone is welcome at the Center on Halsted.

Annual events
Chicago Pride Parade

Welcome to the party that attracts people of all sexual orientations from all over the globe. Celebrate gay pride in Boystown on the last Sunday of June. It was first held in 1970 in front of several hundred appreciative supporters. By 1990, that total reached 100,000, and the mass of people on the streets of Boystown surpassed a million in 2013.

Northalsted Market Days

If you're going to be in the Windy City in August, the Midwest's largest festival is held over a two-day period this month. Its highlight is the live music that has been performed by singers such as Olivia Newton-John and Joan Jett over the years. Your mouth will likely be watering when you see the food available here, and plenty of merchandise is on sale to ensure that you can take home souvenirs from this vibrant event.

The L

Boystown is conveniently connected with downtown and the rest of Chicagoland via the L train system. One of its most convenient stations is Addison, which is located across the street from Wrigley Field on the edge of the neighborhood's western border. Regardless of whether you are taking a bus, train or plane into Chicago, the L can take you around Boystown during your stay. A trip from O'Hare International Airport will necessitate a trip downtown and a change of trains.


If you are in Boystown during the winter, make sure to bring warm clothes, as the weather can be extremely cold that time of year. Average low temperatures in January are in the teens.

A trip that coincides with one of Boystown's fun summer celebrations will allow you to enjoy temperatures in the 80s or high 70s. Grab some drinks and enjoy all that this vibrant neighborhood has to offer.


Chicago South Loop Hotel

Weekend trip to visit family

Much nicer and less expensive than some airbnbs we have used in the area. Positives: Convenient to local family, Lobby, hallways and room were all clean and fresh. Beds were clean and comfortable. Negatives: Room lock didn't work requiring new batteries, which was fixed promptly. Tried to use Business Center for airline check-in and print boarding passes but the printer had no extra paper and didn't work; asked Sunday morning receptionist to resolve and she responded rudely that she was the only person on duty, didn't come to resolve the issue. Pole light in room was broken. Requires a deposit upon check-in.

A verified traveler

3 weeks ago


Hyatt Regency McCormick Place

Chicago auto show stay

I chose the Hyatt because of 4 things. 1. The rate was a great value. 2. Considering the amount other hotels were charging for the parking, the combined price of the room and parking made the price a bargain. 3. This is a 4 star hotel and the quality of the room was excellent. 4. The hotel is attached to the convention center and the convenience of not having to drive to the auto show was very relaxing. The hotel put a notice under the door the evening before check out that there was a large number of check outs the next morning and to please observe the 12:00 check out time and use online or in room check out if possible. Bit, they let you know on this notice to hold onto your room key and if parked in the garage, you could remain parked there at no additional charge until 8:00pm. This worked out great for me as I didn't have to worry about moving my car until I left Chicago to head home. Excellent stay.

A verified traveler

5 days ago


Wyndham Grand Chicago Riverfront

Great Location

The wyndam grand is a very nice hotels, modern lobby with a bar connected to it. Wonderful location right on the river, within walking distance from many resturants and shops. The room was just okay, staying in the premier suite, the room is a little on the older side. But my main issue is with the cleaning of the room. I noticed alot of things are dusty, also when we entered the room there was garbage on the floor in the living room area. Overall great hotel and location, housekeeping leaves something to be desired.

A verified traveler

4 days ago


Palmer House a Hilton Hotel

Beautiful hotel close to the Loop

This hotel is stunningly beautiful, close to many shopping venues, Millennium Park, the river AND Lake Michigan. It is also really close to highway access. I only have a few complaints: 1) Parking is not included or validated in the hotel, and the official hotel parking garage is $43 PER NIGHT. ABSURD. 2) Quality of the linens was very, very poor. Not good.

A verified traveler

3 weeks ago