17 responses

  1. Medha
    September 8, 2017

    This is fantastic! You’ve summed up the best things to do in a short period of time. I love the Chicago skyline, Skydeck is a place i would want to visit for the views! Thanks for sharing, this is useful information.


  2. Miranda
    September 8, 2017

    Love Chicago! Being so close to it, I’ve done most of these things already. I’m a huge lover of deep dish pizza, NYC pizza can’t even compare! I’ll have to try Pequods next time I’m there.


  3. amit
    September 8, 2017

    Chicago is high on my list for when I do my USA trip, although there are some bits of Chicago I do know about but you’ve noted a few I didn’t so thanks, Cant wait to have a Chicago deep dish haha 😀


  4. Justine
    September 9, 2017

    The view of Chicago from the top looks similar to NYC. Anyways, does it snow in Chicago? I’ve been wanting to go but still haven’t been.


  5. Carol Colborn
    September 9, 2017

    Been to Chicago several times but my biggest regret is not having gone to Millennium Park and see the Bean! But I always have deep dish pizza!


  6. tessa
    September 10, 2017

    What a great post, Chicago is one of my favorite US cities! I find myself looking for flights with layovers there just so I can get some of their great food, especially Garett’s Chicago mix popcorn!


  7. Christopher Mitchell
    September 11, 2017

    I will definitely be bookmarking this, as I’m hoping to get to Chicago sooner rather than later! It’s particularly enticing to me because I’m a massive sports fan, and I hear nothing but good things about Wrigley Field, which you also seem to suggest is something worse seeing!


  8. Charles McCool
    October 27, 2017

    When I think of Chicago food, well beside dogs and pizza, I think of Twin Anchors. I will check out your other suggestions next time I visit.


  9. Eryn
    March 5, 2018

    Love this post! I’ve never been to Chicago, but it’s on my bucket list!


  10. chloe
    April 7, 2018

    I have done #1, #3 & #8. I visited Chicago right after Chicago won the hockey championship as the entire town was celebrating. It was such a memorable experience.


  11. Eric Gamble
    September 11, 2018

    I cant believe I haven’t been to Chicago yet! It is definitely on my bucket list! I have never even heard of Maggie Daly Park but that place sounds like a hidden gem. Though I am not a cubbies fan, seeing a game in Wrigley and eating a hot dog sounds awesome.
    I know for a fact Darcee would love to explore the Navy Pier too…she has always wanted to ride the ferris wheel there! Such a unique city to just stroll around!


  12. Amanda Dunn
    October 16, 2018

    I LOVE downtown dogs! And I totally agree about navy pier! Was definitely not a fan. But I LOVE Chicago!


  13. Kalyan Panja
    August 12, 2019

    So thankful I found this! I am feeling more confident about my coming solo travel to Chicago. I will be there the beginning of October for 3-4 days. Not a planner, so this is a big challenge for me.


  14. Chuck Loya
    March 20, 2021

    Thank you for all the great insights and information. We are planning to do a road trip that includes Chicago as Chicago has been our bucket list for a long time. We won’t be in a rush to do everything in the 48 hour itinerary timeframe and wondering how many days do you think we might want to stay without over-staying our trip? Thanks!


    • savvyglobetrotter
      April 26, 2021

      I don’t think you can ever over stay in Chicago because there is so much to do. If your time is short you should be able to see most of the major attractions in 2 to 3 days.


  15. Scott Wiley
    May 8, 2021

    The absolute MUST stop for anyone visiting Chicago for 48 hrs…

    Go to the Adler Planetarium and turn around.
    Best view in the entire city. Bar None.


  16. Sarah Alroumi
    May 19, 2021

    Wow amazing guide! Chicago is such a beautiful city! Ive been to half of those places a couple of years back! would definitely visit the other places you recommended! I would also add if you’re ever back in the city you should try firecakes donuts they’re really good.


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