A Weekend in Chicago

Chicago – weekend itineraries & ideas

Chicago is a nice central hub for us, so we’ve been making more frequent trips to the area lately.   I’ve included details on the specific trips we’ve done as well as other sites that could be added on if you’ll be in town longer.  Several links are posted throughout for more in depth blog posts about those specific activities.

Weekend 1: (Saturday afternoon through Sunday afternoon)

  1. Concert or game at Wrigley field – We went to the Luke Bryan concert at Wrigley last August
    • We got there a couple hours before the concert and paid to park at a restaurant nearby.  Then we wandered around the area & stopped off for some drinks.  We figured we’d be parked in and have to wait awhile after the concert to leave, but we lucked out and had no problem.
  2. Willis Tower Skydeck
    • The views were great, but I’m not going to lie it felt like we were in Disney World.  After entering the building there was a long weaving line.  Then you get filed onto an elevator and go to the basement where there is another long weaving line.  There is a booth where you can purchase a “Fast Pass” which does save a lot of time, but we were trying to be frugal and skipped it (although if you’re paying for parking in the lots nearby it may not be that much more expensive to buy the fastpass when you think about the money saved on parking…).  There were videos and informational displays along the lines, and I really didn’t mind waiting.  After buying tickets, there are more lines… then you watch an informational video and THEN you take an elevator up to the skydecks.
  3. Giordono’s pizza
    • After the Skydeck we walked to Giordono’s.  They told us ordering the deep dish pizza could take 45min to 1hr to prepare, which was good to know ahead.  We ordered one and it was AMAZING.  Can’t wait to go back!
Willis Tower Skydeck - Chicago, IL
Willis Tower Skydeck – Chicago, IL

(Where Ferris stood in the movie Ferris Bueller’s Day Off!)


Weekend 2: (Saturday morning through Sunday afternoon)

  1. The Field Museum
    • We parked at Soldier Field, and spent about 3 hours at the museum.
  2. Drinks at Northside Bar & Grill
  3. Dinner at Saved by the Max (A MUST VISIT for any Saved by the Bell fans!)
  4. Checking out famous houses from the movies (Home Alone, Ferris Bueller’s Day Off, Sixteen Candles, etc.)
    • The Home Alone House was being worked on!  There was a large fence around the house with security cameras and no trespassing signs.
    • To find addresses of famous houses I use RoadTrippers website
Field Museum - Chicago, IL`
Field Museum – Chicago, IL` – Dinosaur


Saved by the Max, SBTB
Saved by the Max – Chicago, IL


Other places I’ve been in Chicago but it’s been awhile… if you’re in town another 1/2 day or so, any of these would be fun to check out.

  • Shedd Aquarium (This one is my favorite!)
  • The Art Institute of Chicago
  • Museum of Science of Industry
  • Lincoln Park Zoo (Free zoo, but have to pay for parking)
  • Wandering around Navy Pier – we did a boat tour, saw the Bob Newhart statue, and shopped
Lincoln Park Zoo - Chicago
Lincoln Park Zoo – Chicago, IL

Places in Chicago I’m planning on in the future

  • The Planetarium
  • Frank Lloyd Wright tours
  • Millennium Park
  • The Bean
  • Boat tours or kayaking on the River
Lincoln Park Zoo - Chicago
City view from Lincoln Park Zoo – Chicago, IL

Things NEAR Chicago, that are fun to add on are:

  1. Shopping at IKEA
  2. Dinner show at Medieval Times (great show)
  3. Indoor Skydiving at iFLY (so amazing!)
Medieval Times
Medieval Times dinner show


iFly – Indoor skydiving

Chicago is such a great place to visit!  I can’t wait to head back.  What are your favorite things to do there?

25 thoughts on “Chicago – weekend itineraries & ideas

  1. My first weekend in Chicago was identical to your weekend 1. For me, a trip to Chicago is not complete if I don’t eat at a Giordano’s. That’s the one thing I feel I need to do every time!

  2. How did you like the indoor skydiving? Going to look at famous movie homes sounds very cool, it must be weird to see the Home Alone house in real life! I’d love to return to Chicago and do the Frank Lloyd Wright tour.

    • The indoor skydiving was so much fun! The instructors were really good at it, and at the end of each groups session, they’d do tricks in the wind tunnel. I’d definitely go again :)

  3. Oooh, I want to check out the skydeck, though I’m sure I might get some vertigo when I go! I know it’s kind of for kids, but the Chicago science center is one of my favorite things to do in Chicago. Was indoor skydiving expensive and/or scary? I’ve always wanted to try it and it’s one of those things that’s on my bucket list but I never seem to get around to it!

    • I’ll have to check out the Science Center sometime, good to know! The indoor skydiving was a little expensive, but worth the experience. We bought a package for 2 people that was 2 minutes per person. That didn’t sound like much time for the wind tunnel, but it was plenty for our first time! We did 1 minute at a time, and my muscles were getting tired by the end of our 2nd minute :) I was a little nervous about the wind tunnel, but once it was our turn it was all good. It’s nice because we could watch other people in the wind tunnel from the waiting area, so you knew more what to expect. I was also surprised by how many younger kids were there with their parents.

  4. There is so much I’d love to do in Chicago, I really need to make that city break happen – one of my husband’s all-time favourite films is Ferris Bueller’s Day Off, and I hadn’t even thought of trying to do a Ferris-themed tour of the city. That’s going on my list! Thanks for linking up with #citytripping

  5. I can’t believe I spent so much time in Chicago and didn’t realise Ferris Bueller and Hone Alone was filmed there! The Art Institute, Shedd & Field Museum were great. The children’s museum and the butterflies at the Nature Museum were great too. #citytripping

  6. I grew up outside of Chicago so I have done many things on this list. Great collection. My sister used to work at The Shed Aquarium and I would get to go to work with her. I loved it! It is amazing and should be on everyone’s list. I would like to go back and do the river architecture tour. I’ve heard great things about it.

    • That’s so awesome that your sister worked at the Shedd! Glad to hear you’ve heard good things about the architecture tour, I’m excited to check that out when the weather is nicer.

  7. Chicago offers such a great deal of activities and sights that is one is spoilt for choice. These itineraries hold the promise of great times including some great food. Would love to take in all the sights and sounds of Chicago and have a really immersive experience in the city. Will refer to these itineraries when we plan our own itinerary for Chicago.

  8. I need to go back and explore more of Chicago! My friend actually just moved up there!! This seems like the perfect little weekend getaway…now I want to goo :( Anything that has to do with pizza is definitely on my list!

  9. Wow – that first picture gave me vertigo – how awesome to be so high up and such an amazing view over the city. I’ve not spent much time in America but hoping to road trip there next summer. Chicago is definitely on the list of must-see places!

  10. The from the tower Skydeck looks awe-inspiring and worth the wait. one hour waiting for a pizza is too much thinks, isn’t it? But all good when it tastes good :) Field Museum looks luke a great place to be with kids and Indoor Skydiving at iFLY sounds interesting too. Chicago is a great place indeed :)

  11. I’ve been to Chicago lots of times, as it’s a pretty close drive from where I live. There is so much to do there. I like to walk along Michigan Avenue and look at all the stores. I also love going to the Lincoln Park Zoo. Especially because it’s free! My sister and I once did a whole weekend there that we filled by checking out different pastry shops and bakeries!

  12. I feel Chicago has a lot to offer. This is a great post for travelers, who are looking for the weekend getaways. I personally would like to try a sky deck. That sounds quite exciting to me. How was your experience with indoor skydiving?

    • There really is something for everyone & so much to do in Chicago. I loved the indoor skydiving, it was so much fun!

  13. Really nice post :) well as Italian I would opt for weekend 1, so I could try the pizza in Chicago ahahah, I’m too curious Anyway last week I saw a Video on “Insider” about Willis Tower, the view from there is absolutely amazing :D and a little bit scaring I think.

  14. Chicago is one of the best cities in the US. The food there is absolutely amazing. Just love the images as well. How was the experience from the top? Were you scared a bit. I have heard its a great experience for people who want to overcome their fears of heights.

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