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Chicago Tourism and Gay Friendly Nightlife

I'm visiting Chicago Labor Day Weekend for a wedding. It's my first time in the city so I'm staying a couple of extra days so that I can tour the city a bit. I'm on a cheap to nothing budget. I have 3-4 days free to do anything outside of the wedding. What are the main sites should I visit during the day?

How is the gay nightlife scene on weeknights? I'll be free Sunday through Tuesday nights (Monday is Labor Day) and leave on Wednesday. Probably not the best for the bars, but I hope to go out and see whatever is around. Any advice? Any websites to look up events or things to do that week?

3 Answers

top answer by
Derek from Seattle

During the day, go see Grant Park. That will get you the The Bean and the fountain, both of which are cool. You'll have good luck going out in Boystown any night of the week, especially during summer.

Mentioned in this answer:

  1. Grant Park (attraction)
  2. The Bean (attraction)
  3. Boystown (neighborhood)
5 thankscomments (1)

answered by
Dabs from Chicago

Jazz Fest is in Grant Park August 29-31, that's free.  Millennium Park sometimes has free concerts as well.  The Chicago Water Taxi should still be running, take that to Chinatown or just for a ride on the river if your budget doesn't extend to one of the boat rides from Wendella, Shoreline, etc.  All of the museums have a charge and most are fairly expensive but all worth the money if you have a particular interest in one of them.

Boystown, as mentioned, should have activity, certainly on the weekends

The lakefront path is quite nice, if you can't afford to rent a bike, you can see if the Divvy program works for you or you can do part of it on foot.

Mentioned in this answer:

  1. Grant Park (attraction)
  2. Millennium Park (attraction)
  3. Chinatown (attraction)
  4. Wendella (attraction)
  5. Shoreline (attraction)
  6. Boystown (neighborhood)
3 thanks

answered by
Jillian from Los Angeles

I've lived in Chicago for 8 years, and although downtown and near north areas are great, I would recommend taking one of your days to check out an up and coming or new neighborhood! If you want to get away from the tourists, Chicago really has some amazing, unique, and less crowded neighborhoods that are worth exploring. 

Definitely hit up Lakeview/ Boystown, but also consider checking out Logan Square, or Wicker ParkBucktown

I lived in Lakeview for a few years and recently went to a new place with a great beer list called DryHop Brewers.Take the red line to the Belmont stop and walk from there. Head north from there and you'll be in a good spot for fun nightlife! 

Also, definitely check out the waterfront by Belmont Harbor for a great view of the city. Take a walk on the path, or relax in the sun!

West of the city you can check out Logan Square, which has seen insanely amazing restaurants (Longman & EagleFat Rice to name a few), emerge in the last few years. Talk a walk around Logan Boulevard and pop into New Wave Coffee for a morning cup. Every Monday night at the Logan Theatrethey have live comedy which is a different budget friendly option.

For a little more sceney hood, head to Wicker Park on Division or corner of Milwaukee/North/Damen in Bucktown. Great tacos for $3-4/each? Try Big Star. Unless you get tacos to go, be prepared to wait (it's worth it!). You can catch a bus, or take the blue line from downtown straight to the Damen stop. All of these areas are just fun to explore/walk around in.

Also, if you're free on Sunday night, it is the last night of the North Coast Music Festival in Union Park. Maybe you could get a last minute ticket for cheap?! Just throwing it out there as an option.

Enjoy Chicago and let me know if you have any other questions!

Mentioned in this answer:

  1. Lakeview (attraction)
  2. Boystown (neighborhood)
  3. Logan Square (attraction)
  4. Wicker Park (neighborhood)
  5. Bucktown (neighborhood)
  6. DryHop Brewers (attraction)
  7. Belmont Harbor (attraction)
  8. Longman & Eagle (restaurant)
  9. Fat Rice (restaurant)
  10. Logan Boulevard (attraction)
  11. New Wave Coffee (restaurant)
  12. Logan Theatre (attraction)
  13. Big Star (restaurant)
  14. Union Park (attraction)
2 thanks

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