3 Days in Chicago

In June 2014 we were fortunate to have 3 days in Chicago to explore all the Windy City has to offer. This post is the second part in how we spent our final 2 days in Chicago. You can read how we spent our first day in Chicago HERE.

 Our itinerary for Day One was:

Day Two

Our second day in the Windy City started out cold, rainy and yes, windy. We continued to put our Go Chicago card to good use on our final 2 days, even when the weather turned against us. We decided to spend some time indoor, exploring some of the amazing museums that Chicago has. We spent the morning at the Shedd Aquarium.

*note: this post does contain affiliative links. We purchased our Go Chicago cards and we were not financially compensated. However, If you book through our links we may make a small commission. Thank you!***

Art Institute of Chicago

The Art Institute of Chicago

We then headed over to The Art Institute of Chicago. This was a place that I desperately wanted to see! I must admit, that aside from my Art Appreciate capstone class I took in college, I know very little about art. But I was excited to learn more! Jake…not so much. We got our brochure and the only thing that looked familiar was the picture below. So we spent the next hour exploring solely looking for the Farmer and Wife picture, which is apparently named American Gothic.

American Gothic (Grant Wood, 1930)

American Gothic (Grant Wood, 1930


Head of Buddha (Java, Indonesia, c. 9th century)

The Asian department was absolutely fascinating to me! It’s unbelievable to think about how old some of the pieces are, such as the Buddha head above from the 9th century.  Jake eventually became restless, so we cut our visit short and headed to Millennium Park to visit Cloud Gate, aka The Bean.

"The Bean"

“The Bean”


Under the Bean

Under the Bean

It was a lot of fun taking ‘selfies’ in the reflection of The Bean. We definitely weren’t the only ones either!


We then spent the rest of the day exploring around our Magnificent Mile hotel and picking up some Chicago Cubs gear for the next day!

Day Three

We only had 2 free nights at the Hyatt Magnificent Mile hotel. It was a beautiful hotel and fantastic location, but at $300/night our room was definitely not in our budget! So we packed our backpacks and headed to HI-Chicago hostel near Grant Park. We loved the location of this place and the free breakfast was pretty good as well. We paid $111 for a private room with a shared bathroom. 

We then put our Go Chicago card to use again and visited both John Hancock Observatory and the Willis Tower Skydeck.


The John Hancock Observatory is now called 360 Chicago, although we didn’t hear anybody call it that. Aside from the stellar view, our favorite part was experiencing Tilt. You can see videos of what it is here. You basically hold onto two bars over a window and the window tilts so that you are looking over the Magnificent Mile, 1,000 feet above! The height may be scary for some; my fear was that I would loose my grip and fall through the window! There wasn’t a line for Tilt when we visited before noon.

Willis Tower Skydeck

Willis Tower Skydeck was formerly and more popularly known as the Sears Tower. As you can see, the views from both of these buildings are stunning! The best part of Skydeck is The Ledge, a clear floor balcony which allows you to see the 1,353 feet to the ground. A few weeks before our visit there was a lot of chatter about the ledge reportedly cracking while tourists were on it. Skydeck denies it, and says it was just the flooring settling. Either way, we were nervous.

The Skydeck is 103 stories high, which makes it the highest observation deck in the United States, and the 8th tallest building in the world!  There were lines to each of the Ledge balconies, unfortunately they were all about a 20 minute wait while one person after another steps out to pose for a picture. We had our picture taken, but they didn’t turn out well because of the bright sunshine. But at least we will always have the memories 🙂

wrigley field

We ended our final day by taking the train to Wrigleyville and taking in a Chicago Cubs game at Wrigley Field! We were fortunate to visit in 2014 which was the 100 year anniversary of Wrigley Field. Eating popcorn and a hot dog, cheering on the Cubs as they won and just soaking in the atmosphere here was one of our favorite moments of 2014. This is definitely a MUST when in Chicago!

wrigley field


chicago baseball

If You Go


  • Art Institute of Chicago: Admission prices: Student- $17, Adult- $23, Adult Fast Pass- $33
    • Art Institute Website 
    • Combine your visit with nearby Millennium Park or Willis Tower
  • John Hancock Observatory (360 Chicago): General admission-$19, Fast Pass-$38
    • Tilt Tickets are $7 per person, can buy for a specific time online or buy when you get there as we did (there wasn’t a line)
    • 360 Chicago Website
  • Willis Tower Skydeck: Gen Admission- $19.50, Fast Pass- $45
  • Wrigley Field: We paid about $30 for 2 seats in the MasterCard century seats section. You buy your tickets online and use your MasterCard at the entrance and they print your tickets
  • HI-Chicago Hostel: $32/night for a dorm bed or $100 for a double private

Go Chicago Card

We used our Go Chicago Card for 6 activities in our 3 days in Chicago. The Go Card gave us access to the Fast Pass lanes when applicable (which is totally worth it, being able to skip the long lines!). The Go Card gives you access to 26 LOCATIONS! We didn’t see all we could have seen with the card, but we were happy with the attractions we did see.

Attractions: The Field Museum ($31), Shedd Aquarium ($30.95), Shoreline Architecture River Cruise ($32), 360 Chicago ($38), Willis Tower ($19.50) and Art Institute of Chicago ($33).

Total Cost if purchased individually: $184.45

Cost of 3 Day Go Chicago Card: $136.99 (it was on sale when we bought them, about $20 less but I am using the current pricing for the Go Card and all the attractions listed)

Total Savings: $47.46 per person

So you could obviously save a lot more the more you see. But saving almost $50 per person makes it at least worth it! And it made it a lot easier only having to worry about one card for everything instead of juggling tickets.

3 days in ChicagoTell us about your experience in the Windy City! Did you love Chicago as much as we did? 

13 thoughts on “3 Days in Chicago

  1. I really enjoyed this article. I haven’t been to Chicago in a few years and my husband and I were just talking about scratching this Chicago itch we both have. I’ve done all the things on the list and I think you captured a great offering of what Chicago offers. I would recommend, for the future, the architecture tour by boat and a visit up to Lincoln Park. I love eating in Chicago,too! Glad you had a great trip and your pictures were great and fun. 😉

  2. That is awesome that you got to catch a Chicago Cubs game during Wrigley Field’s 100th Anniversary. Next time you go back to Chicago for a Cubs game, make sure you go on the Wrigley Field tour. These tours are available daily whether the Cubs are at home or on the road and give you a newfound appreciation of how difficult it really is to play inside Major League Baseball’s second oldest stadium.
    Ray recently posted…Wrigley Field TourMy Profile

  3. That is awesome that you got to catch a Chicago Cubs game during Wrigley Field’s 100th Anniversary. Next time you go back to Chicago for a Cubs game, make sure you go on the Wrigley Field tour. They are available daily between April and October whether the Cubs are at home or on the road. You learn a lot about the history of baseball and how difficult it really is to play inside Major League Baseball’s second oldest stadium. It definitely made me appreciate their 2016 World Series win that much more.
    Ray recently posted…Wrigley Field TourMy Profile

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