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We decided to doing a little exploring when we had 72 hours in Chicago last year. I decided that I wanted to buy my husband tickets to a Chicago Bears game for his birthday. Michael & I love a good road trip so we decided to make it a weekend trip! (We live about 6.5 hours away from Chicago so driving all of that in one day is too much for us.)

Day 1

We parked our car in a parking garage near our hotel and set out on foot. As we walked, it started to snow and be a tad windy. Typical Chicago (beginning of) winter weather! We started out by visiting Billy Goat Tavern when we got to Chicago. You’ll remember this place if you are SNL fans like us! We, of course, had to have cheeseburgers and shared some fries. They did not disappoint, they were so good!

Short on time in Chicago? Going to a Bears game and want to see other sights? Here's how to spend 72 hours in Chicago!
Short on time in Chicago? Going to a Bears game and want to see other sights? Here's how to spend 72 hours in Chicago!

After our lunch, we decided to walk down Michigan Avenue, The Magnificent Mile, as the rain had let up! We walked along the shops and got some candy at Dylan’s Candy Bar. I’d never walked down Michigan Avenue and with the holiday lights, it was pretty magical to this small-town gal!

Short on time in Chicago? Going to a Bears game and want to see other sights? Here's how to spend 72 hours in Chicago!
Short on time in Chicago? Going to a Bears game and want to see other sights? Here's how to spend 72 hours in Chicago!

This happened to be a weekend where they were having the million lights parade & lights festival so we hung out for it. We had a glass of wine at Eno to keep warm before it started. The parade was so cool! It was quite long, but it was so cool to see those big parade balloons in real life. It reminded me of the Macy’s parade on a small scale. I’ve never seen a parade like it before!

The only downside was getting back across the river was tough. A lot of the streets were blocked off and we didn’t really know how to get back across. We had to figure it out on the fly and it was a tad bit frustrating. I’d definitely recommend getting an uber or doing a little more research than we did if you are going to see that parade.

We headed back to our hotel and got ready for our dinner reservations at The Gage which was conveniently a block away from our hotel. We got in and seated immediately and had a very romantic dinner! Hubby had lamb and I had salmon. Their Ceasar salad was so good as well! After that, we headed down Jewelers Row and had a few drinks and played some darts before we turned in for the night.


Read Next: Where to Stay in Chicago


Day 2

The next day, we decided to get up early so we could go see Cloud Gate AKA The Bean! My husband had never seen The Bean in person before, even though he’d been to Chicago, so we had to swing by to see it! (If you get the chance, Millenium Park has a massive Christmas tree that is a must-see.)

Short on time in Chicago? Going to a Bears game and want to see other sights? Here's how to spend 72 hours in Chicago!

We took the traditional Bean selfie and Bean reflection photos and caught an Uber down to Solider Field. There is an early pre-game tailgate happening between Soldier Field and the museum that we decided we wanted to check out. It wasn’t too crowded yet so it was nice. We had a beer outside the stadium as we waited for the gates to open and enjoyed the atmosphere. It was our first Bears game and it was awesome to be among our tribe!

Short on time in Chicago? Going to a Bears game and want to see other sights? Here's how to spend 72 hours in Chicago!

Then it was time for the game! Unfortunately, the Bears lost, but we had a blast anyway. We went to the Lions versus the Bears, so there were a lot of Lions fans there. We got hot chocolate in commemorative hot chocolate cups we still use today. It was so cold that our hot chocolate froze! We stayed pretty warm until toward the end of the last half. You definitely need to wear a good set of thermals if you are going to a Bears game!

We headed back to our hotel to shed some layers and then headed to Velvet Taco. OH MY! These were some of the best tacos we’ve had while traveling. We will definitely make it a point to go there next time we go to a game.

After our tacos, we decided to head back to downtown and walk around a bit. While walking around, we decided to go up to the Skydeck in Willis Tower since we figured it wouldn’t be as busy since it was night time. The nighttime views were great (even if they weren’t so great for picture taking), but I definitely want to go back up during the day sometime.

Short on time in Chicago? Going to a Bears game and want to see other sights? Here's how to spend 72 hours in Chicago!

Day 3

The next day we bundled up and got ready for our tour of Soldier Field! I got this for Hubby as a little bonus to his birthday present. He absolutely loved the tour and I have to say it was pretty darn cool!

We learned the history of Soldier Field and got to walk down by the field and through the guest locker room. We also got to check out the VIP area – they have some AMAZING seats. Super cool and would definitely recommend booking a tour if you are in Chicago during one of the times.

Short on time in Chicago? Going to a Bears game and want to see other sights? Here's how to spend 72 hours in Chicago!

After our tour, we, of course, had to go to Giordano’s and have some deep dish pizza before we headed back south!! We got a pepperoni pie and it was amazing (as always). (We also love to visit Lou Malnati’s while in Chicago!)

Short on time in Chicago? Going to a Bears game and want to see other sights? Here's how to spend 72 hours in Chicago!

  1. You definitely made the most of your weekend! I finally visited Chicago last September and loved the little bit I saw. Hoping for another visit with the family in the future. Such a fun city.

  2. […] before I showed my husband Cloud Gate (aka The Bean), I checked it out at Millenium Park. Because you can’t visit Chicago without […]

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