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Things to do in Chicago for a frequent visitor??

We have family there, so I grew up visiting the area at least once a year and doing pretty much all of the touristy things.  DH had never been to Chicago until recently, so we did the typical tourist things on our last two trips.  The only big attraction he may be interested in that we haven't already done is the Museum of Science and Industry.

We're leaving tomorrow for a five day trip to visit family.  Does anyone have ideas of fun things to do other than the big, typical attractions?  Maybe a comedy club, fun restaurant or bar, or a cool area to check out?

We'd love some inexpensive restaurant recommendations (less than $20/pp).  I really don't want to do deep dish pizza this time.  We love ethnic food (but not Chinatown - we did that last time.)  We absolutely loved Ann Sather's and may go back, and Russian Tea Time is one of my favorites in Chicago, if these give you ideas of food that we like.

Re: Things to do in Chicago for a frequent visitor??

  • Also, we'll have a rental car and plan to do hotwire or priceline for a hotel.  We're thinking of staying in the "North Michigan Ave, Water Tower, Gold Coast" area, or is it worth paying $30 a night more to bid on a hotel in the "Magnificent Mile - Streeterville" area?
  • You can go iceskating at millenium park, go to second city or Improv Olympic to see a comedy show.  Improv Olympic is in Wrigleyville and there are a bunch of fun bars around there to get food/drinks at.  As for restaurants I'd recomend Heaven On Seven--great food (southern comfort)/service for a great price and you have to get their cornbread-its the best I've ever had!

    have fun :)

  • Honestly, those areas are pretty much the same thing so stick with the cheapest one. ?Keep in mind you'll likely pay a pretty penny to park the rental at the hotel, so if you are in an area where you can take the Metra commuter train in to the city it might be a better option. ?The El, busses, and even a cab will likely save you money on that. ?

    As for things to do, check out metromix.com, and chicagoreader.com. ?Both will have several listings for fun events going on this weekend. ?I'd say get out of the downtown area and check out neighborhoods. ?There are TONS of cute little restaurants that you can stumble upon that won't be as expensive as eating in the more touristy areas and you'll have a greater range as well. Second City is always a good choice and there are several restaurants nearby on Wells St. ?Improv Olympic is in Wrigleyville and there are a ton of restaurants and bars in that area, but it's definitely a younger crowd and often obnoxious, IMO.

    ?Andersonville has some cute places if you're looking for something a little more laid back. ?Hopleaf is a fantastic bar with tons of Belgian beers and microbrews, and they have a decent menu as well. ?It gets crowded so go early if you're eating, but it's chill. ?There's also a place not quite a full block up called the Icosium Crepe Palace, which is one of the hidden city gems - go hungry and get a dessert crepe. ?

  • Check out Ras Dashen in the Edgewater neighborhood for FANTASTIC Ethiopian food.  It's near the Andersonville neighborhood mentioned by someone above.

    I have to agree with getting out of downtown and checking out the neighborhoods.  Maybe pick up a Not For Tourists Chicago book? 

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