Chicago in a Weekend – Itineraries & Ideas

If you’re planning a trip to Chicago for a weekend, you won’t want to miss out on these customizable itineraries!

Weekend 1:

Saturday afternoon through Sunday afternoon

Concert or game at Wrigley field (Day 1)

Arrive a couple hours early to make sure you can find parking.  Some nearby restaurants sell spots in their lots, but it’s worth doing a couple loops to see the best options before you commit to anything.  **Beware, you may get parked in and have to wait for other cars to move before you can leave your parking spot.

After parking, wander around, stop off for some food or drinks, and do some shopping to fill time before heading over to the stadium.

Address: 1060 W Addison St, Chicago, IL 60613

Wrigley Field - Chicago, IL
Wrigley Field – Chicago, IL

Willis Tower Skydeck (Day 2)

This famous 110 story skyscraper in Chicago sure has great views, but the lines feel a lot like Disney World.  After entering the building you join a long weaving line, this leads to an elevator which takes you to the basement.  From there, you join another long weaving line.

Willis Tower Sky Deck - Chicago, IL
Willis Tower Sky Deck – Chicago, IL

There is a booth that sells a “Fast Pass” which saves a lot of time.  It probably depends on the day (& number of people in your group) if it’s worth paying to skip ahead in line vs. the cost of parking if you’re paying by the hour at a ramp.

Thankfully there are videos and informational displays to help keep people occupied in all the lines.

After finally buying tickets for the Skydeck, don’t get too excited… why? You guessed it… you will again join another line.  This one does eventually lead to a theater that plays another informational video and THEN  you take an elevator up to the Skydeck.

There is a small gift shop on the Skydeck level, and people walk around admiring the views out the windows in each direction, but if you want a picture standing in one of the famous glass bottom sky boxes to admire the city below you… yup, another line.  Honestly, the lines weren’t that bad, so long as you have good company, and are not in a rush!

Address: 233 S Wacker Dr, Chicago, IL 60606

View from Willis Tower Skydeck - Chicago, IL
Gorgeous views of Chicago from the Willis Tower Skydeck

Giordono’s pizza

After the Skydeck walk to Giordono’s for supper.  Be prepared to wait again, but it is worth it for this pizza!  Prior to ordering, our waitress told us the deep dish pizza could take 45 minutes to an hour to prepare.  There are quicker options, but when in Chicago… deep dish pizza is the way to go.

Address: 223 W Jackson Blvd, Chicago, IL 60606

 

 

Weekend 2:

Saturday morning through Sunday afternoon

The Field Museum (Day 1)

The popular Science & Natural History museum in Chicago which boasts a wide variety of exhibits including: Inside Ancient Egypt (mummies!), Nature Walk & Messages from the Wilderness (taxidermy animals & dioramas – DON’T MISS The Tsavo Lions – the lions that the movie “The Ghost and the Darkness” were based on), dinasour bones – say “hi” to SUE the T-rex!, gemstones, and more!

Paid parking may be available at Soldier Field, which is very convenient (depending if there is a game or not!)  One could easily spend an entire day at this museum, but I would recommend a minimum of 3 hours to see the highlights.

Address: 1400 S Lake Shore Dr, Chicago, IL 60605

Tsavo Lions - Man eating lions - Chicago, IL
The Tsavo Lions – Man-eating Lions in Kenya 1898

Northside Bar & Grill

Unwind with some drinks before heading to dinner.

**This was very close to Saved by the Max, so it was convenient to not have to move our car from street parking!  Saved by the Max is no longer in Chicago**

Address: 1635 N Damen Ave, Chicago, IL 60647

Dinner at Saved by the Max

(A MUST VISIT for any Saved by the Bell fans!)

**Update – this location was a pop-up and is no longer there, however there are plenty of other nearby dining options

Saved by the Max - pop up restaurant in Chicago, IL
So much nostalgia at “Saved by the Max” – who else loved SBTB?!

Spot famous film locations (Day 2)

Chicago is the home of MANY famous movies and TV shows.  Some favorites that have film locations worth a visit include: Home Alone, Ferris Bueller’s Day Off, and Sixteen Candles.  The Home Alone House was like a dream!  However it was under construction when we visited.  **Remember, many of these famous sites are peoples actual homes, DO NOT TRESPASS.

To find addresses of famous film locations, I use RoadTrippers website

 

Other Chicago attractions to consider:

(Each of these I would recommend taking at least an extra 1/2 day for)

  • 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)
  • Wander around Navy Pier – consider a boat tour, stop by the Bob Newhart statue, and do some shopping!
Lincoln Park Zoo - Chicago
Lincoln Park Zoo – Chicago, IL
Lincoln Park Zoo - Chicago
City view from Lincoln Park Zoo – Chicago, IL

Things NEAR Chicago, to add to your weekend:

  1. Shopping at IKEA
  2. Dinner show at Medieval Times
  3. Indoor Skydiving at iFLY
Medieval Times  Schaumburg, IL
Medieval Times dinner show – Schaumburg, IL

 

Chicago is an amazing place to visit, especially for a weekend!

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Weekend itineraries for trip to Chicago, IL

Weekend itineraries for trip to Chicago, IL Weekend itineraries for trip to Chicago, IL

Originally published 2/20/17 Last updated 8/13/19

25 COMMENTS

  1. Brian | 23rd Feb 17

    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. Suze | 23rd Feb 17

    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.

    • Christie | 23rd Feb 17

      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. Wanderlust Vegans | 23rd Feb 17

    Finding the houses from Home Alone etc is a awesome idea. I would have never thought of that. We’ve been to Chicago before and had a lot of fun just like you. The Willis Tower is a must see.

  4. The Spirited Sloth | 23rd Feb 17

    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!

    • Christie | 23rd Feb 17

      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.

  5. Cathy (MummyTravels) | 23rd Feb 17

    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

  6. Shane Prather | 24th Feb 17

    Chicago is such a blast for a weekend getaway. I do it often as I live in Ohio a quick flight away. Great itinerary!

  7. Elizabeth (Wander Mum) | 25th Feb 17

    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

  8. Lara Dunning | 25th Feb 17

    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.

    • Christie | 26th Feb 17

      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.

  9. Sandy N Vyjay | 26th Feb 17

    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.

  10. Tatum Skipper | 26th Feb 17

    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!

    • Christie | 26th Feb 17

      Chicago is great, especially with friends! Hope you can visit your friend & eat lots of pizza :)

  11. Emma | 27th Feb 17

    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!

  12. Siddhartha Joshi | 27th Feb 17

    I have always loved the skyscrapers of Chicago, but unfortunately couldn’t visit the city when I was in the US. Bookmarking it for future use. Btw any suggestions for good veggie food?

  13. Rashmi and Chalukya | 28th Feb 17

    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 :)

  14. Brianna | 28th Feb 17

    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!

    • Christie | 28th Feb 17

      Pastry shops & bakeries?! Sounds like an awesome weekend!!

  15. Swati & Sam (The tales of a traveler ) | 28th Feb 17

    Your post reminded me of my weekend trip to Chicago. Loved the place. We visited Shedd aquarium and sky deck too and yes next time try to visit Millenium park and the famous Chicago bean. Indoor Skydiving at iFLY sounds fun, we had no clue about that

  16. Suruchi | 1st Mar 17

    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?

    • Christie | 1st Mar 17

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

  17. Stefano uTravelShare.com | 1st Mar 17

    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.

  18. Akmal M | 2nd Mar 17

    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.

    • Christie | 2nd Mar 17

      The skydeck was great! Although I can imagine people with a fear of heights may be more nervous.

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