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1.22.2014

Chicago // Date Night Ideas


there's so many, many things to do in chicago - restaurants, navy pier, millennium park, bars, zoos, museums, even mini-golf.  yet there's so many nights where we're debating what to do or even where to eat for dinner.  sometimes having 400 options makes it hard to pick just one.  so i complied my favorite go-to date night ideas.  sure, i love going to the shedd aquarium, watching live bands, or seeing a bears/cubs/blackhawks game, but i'm talking about my favorite ideas for what to do when you're just thinking last minute 'what are we doing tonight?!'

my personal favorite date idea is definitely wine tasting (or beer tasting.)  chicago now has a winery right downtown.  it's near my place, in the west loop.  city winery has tastings and tours, and it also has a full restaurant for a complete date night.  you can even make your own wine, with custom labels!  it's a pretty fun place.  there's also a lot of wine bars/restaurants scattered around chicago, so you're sure to find one no matter what neighborhood you're in.

stand up comedy is something chicago is well-known for.  it's the birthplace of second city, which has had so many famous people come from there i couldn't even list them all, from belushi to fey to wolfe.  second city is a fantastic date night.  they have the main stage shows as well as shows on the smaller stages if you're on a budget/out of planning time - they are just as hilarious and likely to have last minute tickets available.  since second city is in the heart of old town, they also offer dinner and show packages with a lot of nearby restaurants.  personally, i just eat downstairs (literally, right under the place) at adobo grill.  and by eat, i mean drink margaritas and scarf down inhuman amounts of their made-table-side guacamole.  like wine tasting, second city isn't the only improv game in town so you're sure to find more options near you.

you can also bring out your competitive side.  downtown chicago has a dave & busters.  this shocks city dwellers as much as it does out-of-towners.  but yes, it exists!  i've made john take me there, it's a lot of fun to get competitive and act like a kid again.  i dominated him in air hockey.  there's also sluggers, in wrigleyville, which has indoor batting cages and carnival type games like skee ball.  you can even try your hand at bowling at 10 pin, which i hear is a celebrity favorite (i've never seen one there though.)

drinks with a view is a great quick date option, if you're not planning on a whole dinner.  there's so many places with great skyline views and though the martinis at the signature lounge on the 96th floor of the john hancock building will run you upwards of $12, the price is worth it.  i also recommend the terrace at trump tower (if you go on a wednesday/saturday during the summer, you see fireworks at eye level) and the shanghai terrace at the penninsula hotel.  obviously these places serve food as well - but it's expensive.  best to have just a cocktail or two, and maybe an appetizer.  the view is something that shouldn't be missed.

restaurants with a (different) view is a great option for an extended date (and you can find places with cheaper options than where you'd go just for a few fancy drinks).  i mean, the whole city is also on water.  well not on it, but you know what i mean.  the restaurants that border the lake are limitless and there's also new options constantly popping up along the river, which winds right through the loop.  (i practically live at south branch during the summer.)  you can even take water taxis to get to them if you wanted!  there's a lot of fancy options, but my favorite has to be bridge house tavern - because you can add bacon to anything on the menu for $2.  if that's not a reason to love a place, i don't know what is.  and for a completely casual option, try lizzie mcneill's, an irish pub right on river before it heads out into the lake.  it's perfect for summer because you can enjoy all the outdoor seating with your pup.  well, hawkeye enjoys it at least.  she gets a hot dog.


what are your favorite date night ideas?

33 comments:

  1. These are great! I've only been to Chicago a handful of times, so we did very tourist-y things. {Daniel took me to Shedd Aquarium for my birthday.} Now that Southwest has a direct flight from Chicago to Memphis, we plan on visiting a lot more. We'll have to try some of your suggestions! But I'm always brainstorming date ideas ahead of time because when it's time for a date we're so indecisive. I made a whole list of them here: http://www.wonderfully-complex.com/2013/09/a-year-of-dates.html

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  2. What great ideas! I love comedy clubs, its been far to long since we have gone.

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  3. When I come to Chicago I want you to take me on a drinks with a view date. If you play your cards right, I might even put out after.

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  4. Ahhhhh. Chicago is on my list of "must go" places! But, it must be warm, I can barely deal with how cold it is here! And when I do come, you can be my tour guide!

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  5. Great ideas! I love that there's a winery IN town. And of course that Second City is located there, where my best friend Tina Fey got her stars.

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  6. i'm with amanda. we'll make a trip of it and then have an orgy if you're nice enough.

    -kathy
    Vodka and Soda

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  7. Love these ideas! I've done most of them with The Boy but we have never taken the water taxi together, and I don't think we have been to Trump Towers together either! Ooh how I can't wait until its warm out again :)

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  8. I wanted to go to a show at Second City soooo badly and I didn't (I think there was just too much to do). Please tell me you eat at a Rick Bayless restaurant weekly? I am convinced that I would turn into a churro if I lived in Chicago. I maybe had his food four times in eight days. Don't judge too harshly...

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  9. All the times I've been to Chicago and I have never been to any of these places. I must be doing it wrong. ;)

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  10. So many fun things to do in Chicago! I love wine tasting and tours. We have a Dave and Buster's here and it is really fun to go and just be a kid again!

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  11. chicago is such a great place!! I miss not living in the middle of nowhere!!

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  12. Love this list! I still haven't been to City Winery but I've been dying to get over there! And Adobo Grill with their guacamole.. I could live off of that stuff. Have you been to Cesars for their giant margarita's? So good!

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  13. All of this sounds like so much fun!!! I have never been to Chicago, but really want to check it out one day! One of the great things about living in a big city is all that there is to do! That is what I miss about living in Atlanta, but it is hard to decide on WHAT to do of those millions of options. Here in Birmingham we pretty much have eating and drinking. We do have Stardome Comedy Club that is fun.

    PS - I want guac now.....thanks a lot! :(

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  14. Chicago is my absolute favorite city to visit. We go every year for our birthdays and we have such an amazing time eating and drinking our way through the city!

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  15. Love wine tasting! I'll have to keep that and drinks with a view on my list when we visit this summer :)

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  16. I LOVE Dave and Busters!! You get to act like a teenager at the arcade, but get the benefit of walking around with a drink in your hand! Best of both worlds :)

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    1. Exactly why I love it! The bar is smack dab in the middle of all the action, and they have Guinness on tap. It's a wonderful place!

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  17. Having a 2 year old crazy train means date night is any night that Mic and I can have a couple hours alone! At this point I am good with a sitting at home and watching a movie without any interruptions :) Before X, I liked going to a sporting event of some sort, heading out to a restaurant in Columbus for dinner, or going bowling. I LOVE and ROCK at bowling :)

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  18. I've only been to Chicago once and want/need to go back soon! can you be my personal tourguide whenever I finally plan a trip!? :)
    -- jackie @ jade and oak

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  19. Chicago and Dallas.... those two cities were my tossup on where to move to. Part of me will always wish I had picked Chi-town (do locals even call it that)

    P.S. Have you been to see Taylor do standup yet??

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  20. Sushi dates are becoming a fav. There are so many options to try and we get to do it together.

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  21. I am DYING To visit Chicago. I'm going to make it a stopover on my way home to Houston next time if at all possible. So many fun ideas!

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  22. Chicago is def on my bucket to visit in the next year or two with my husband so this list will come in handy. Do you have any recommended hotels in the heart of the city that doesn't cost an arm and a leg?

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  23. We're apparently still kids and love doing the night time bowling... when they turn the blacklights on and everything is neon. He always wins but it's still fun!

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  24. these are just awesome ideas in general but i can imagine how fun it would be in chicago. would you please be my personal tour guide?

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  25. I may be coming to Chicago sometime this year (if everything works out). I'll have to keep some of these things in mind!

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  26. My friend just moved to Chicago for work, but he is a comedian. Guess he picked a great city!

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  27. im in chicago right now and lizzie mcneills is across the street from where were staying! perfect timing to read this post :) the wine tasting place sounds amazing!

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  28. Chicago is a day or weekend trip for us, because we live a few hours away, but I love how much stuff there is to do in the area! I just went to Millenium Park for the first time this last fall...

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  29. i love a comedy/improv for date night!

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  30. Thanks for all these great ideas! It is my 21st birthday and my boy friend is flying from Seattle to go out for my birthday. Anyone have any good ideas for fun dance places for after dinner?

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