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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

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.

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

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

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

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!

Things NEAR Chicago, to add to your weekend:

1. Shopping at IKEA
2. Dinner show at Medieval Times
3. Indoor Skydiving at iFLY

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

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