Chicago Gay and Lesbian Travel Guide

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Dusk over Buckingham Memorial Fountain in Chicago, Illinois

Buckingham Memorial Fountain in Chicago, Illinois (Brand X)

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Chicago Gay and Lesbian Travel Tips

By Matt Link

Head to the Hancock. The lines are longer at the Sears Tower, and even though the John Hancock Building is not as tall, its Signature Room on the 95th floor is a great place to hang out in a lounge and sip a drink while gazing over the city and lake.
Take a LGBT tour. The city's tourism office offers free volunteer-led neighborhood tours, including gay tours of Boystown and Andersonville.
Fly into Midway. O'Hare is one of the busiest and most hectic airports in the world, while the smaller and less busy Midway Airport is closer to the Loop and serves more discount airlines.

Gay and Lesbian Travel Overview: Chicago, Illinois

By Matt Link

The nation's third-largest city is a major hub for every gay or lesbian in the Midwest and a popular gay travel destination. It's a friendly, easy-going city despite its worldly refinement. The Windy City has a huge and very visible LGBT scene, centered in two main areas: Boystown (a.k.a. Lakeview), and lesbian-popular Andersonville. Boystown is about five miles north of the downtown Loop in a triangle bounded by Belmont Avenue, Halsted Street, and Broadway. Read More

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48 Questions | 43 Answers

We will be able to spend 1 day in Chicago with 2 boys age 13 and 17. Which would be better Thanksgiving Day or Black Friday. We want to just walk and look.
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My family of 5 are wanting to go to Chicago this summer. Our kids are 14, 12 and 10. We are looking for a decent hotel that has cooking capabilities, yet is a reasonable price. We want it just outside the city so that we could take public transportation into the city (avoiding the parking fees). Can you please make a recommendation. Thanks.
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I am planning a trip to Chicago for 4 days and 3 nights the first of December. I want to do some shopping and sightseeing, and advice?? I am staying near the loop!
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