Chicago, things to do?

Welcome to the travel board. We would encourage you to peruse the “stickied” thread at the very top of the travel board home page. It has loads of detailed trip reviews and photo journals shared by our fellow TD brethren.

Here is one for Chicago

There are so many Chicago threads. I'll link several to sift through:
- March 2017
- September 2017
- February 2018
- March 2018
- May 2018
- May 2018
- July 2018
- July 2018
- August 2018
- September 2018
- December 2018

Few restaurants that may be missing, which I've been to recently:
- Pleasant House Pub, Dusek's, and S.K.Y. (Pilsen)
- Community Tavern (Portage Park)
- Giant and Son of a Butcher (Logan Square)
- The Loyalist (West Loop)
- Etta (Wicker Park)
- Gather (Ravenswood)

Why did you choose it as an anniversary trip ?

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It seems like most went during the warmer months, I will definitely dive into more of the colder months because it will likely be cold AF and wont be able to do some of the other things you can see/do during summer.

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Plenty of great restaurants, cocktail bars and breweries to choose from. Know for a fact that I've put a good list in one of those threads.

If the weather is 25+ degrees, and wind is bearable, you shouldn't have much issue walking Magnificent Mile and checking out some shops. Otherwise, I always recommend that people walk the boutiques on Armitage (Lincoln Park) and Milwaukee (Wicker Park).

Buying CityPASS will give you access to the Willis Tower, Shedd Aquarium, Adler Planetarium, Field Museum, and Museum of Science and Industry.

Any rooftop bars/spots to check out that are still good during the colder months with nice views/atmosphere?

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Any rooftop bars/spots to check out that are still good during the colder months with nice views/atmosphere?

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- Up & UP (Robey Hotel, Wicker Park)
- IO (Godfrey Hotel, River North)
- J. Parker (Lincoln Hotel, Lincoln Park)
- Cindy's (Chicago Athletic Association, The Loop)

My recommendation would be Up & Up. Sweeping views of the city and there are a lot of great restaurants, bars and cocktails lounges in Wicker Park.
- Dorian and Violet Hour are speakeasy types.
- Etta and Publican Anker are my two favorite restaurants in the six corners area.
- Angry Pig Tavern is the place to grab charcuterie boards and drinks.
- Links Taproom has a good beer list.
- Paradise Park is a pizza spot from the owners of Homeslice and Happy Camper, but this will draw a younger crowd for drinks.
- You're also not very far from Logan Square. Easily accessible via train or Lyft/Uber. Plenty of cocktail bars, breweries, and restaurants in that area.

Good call. I can do that. The sticky gives some good insight, but it's dated and from someone that didn't do much exploring into Chicago's neighborhoods, excluding Wrigley.

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My recommendation would be Up & Up. Sweeping views of the city and there are a lot of great restaurants, bars and cocktails lounges in Wicker Park.

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Spot on!


Great info/insight!! Thanks!

I'm a sports guy, obviously from South La so don't experience too much hockey, but the blackhawks are playing the Friday night when we go and the Bulls play the Saturday night. Don't believe our intentions are to do both...so we'd likely choose. I'm more of a basketball guy, but think experiencing a blackhawks game would be awesome....what you think? or what you think would be best....Bulls play Celts...blackhawks vs Avalanche

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Both teams are dreadful, Blackhawks will be more expensive but will be a good time. I don't see any reason to go to a Bulls game right now.

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Agreed.

See the Blackhawks, especially if you don't get to see NHL games very often, or at all.

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Uber is your friend.

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Agree to an extent, but the 'L' is convenient, dependable on weekends, and not overly difficult to navigate. Only time I would recommend Lyft/Uber is going East <-> West, assuming you want to save as much time as possible.