Your Full Guide to a Weekend in Chicago
Travel Travel Tips

A Full Weekend in Chicago: 10 Things You Must Do

This past Valentine’s Day, Craig and I had big plans β€” we were going to Chicago for a romantic weekend getaway! Flights were booked, our hotel was reserved, and we were ready for our adventure.

And then, we decided to move to Washington, D.C. So, that meant giving up our Chicago adventure to instead save money to help us cover the cost of our move. As much as I was excited to be moving to the District, we were both a little bummed to be missing out on our weekend adventure.

So, when an 8-day work trip this spring included spending over a week in the beautiful city of Chicago, I was over the moon!

Heading to Chicago soon? Check out these 10 must-do things that will give you the perfect glimpse into this beautiful city!

Because this was a trip, we only had time to experience a handful of things in between long work days, which equates to about a full weekend’s worth of adventures in the city, which is more than enough time to take advantage of some of the best things Chicago has to offer!

I’m including 10 things you must do, and broke it down into the things that matter most β€” where to stay, what to do, and of course, where to eat! Happy adventuring, friends!

Where to Stay

1. Book a room at the historic Hotel Lincoln.

Heading to Chicago soon? Check out these 10 must-do things that will give you the perfect glimpse into this beautiful city!

I absolutely adore finding unique places to stay while traveling. When I found out we’d be staying at Hotel Lincoln during our time in Chicago, I was beyond excited! Completely redone while still maintaining its historic charm, this hotel will make all of your boutique dreams come true!

Nestled across the street from Lincoln Park, just a few minutes from the heart of Chicago, the location couldn’t be better. Not to mention the adorable coffee shop in the lobby downstairs, and the views of downtown Chicago and Lake Michigan from the rooftop bar!

What to Do

2. Have a drink at a rooftop bar.

Heading to Chicago soon? Check out these 10 must-do things that will give you the perfect glimpse into this beautiful city!

Now, you didn’t think I was going to mention a rooftop bar and not elaborate, did you? πŸ˜‰ If you decide to stay at the Hotel Lincoln, you can head up to the top floor to have a drink at one of the most popular rooftop bars in Chicago β€” the J. Parker.

J. Parker flaunts a full view of downtown Chicago and overlooks Lake Michigan, making for the perfect romantic spot. Sip a glass of wine or order one of their signature cocktails along with some delicious small plates. Planning your trip during the winter months? They even put up a full glass enclosure for you to stay warm while still enjoying the fabulous views.

3. Spend time exploring Millenium Park.

Heading to Chicago soon? Check out these 10 must-do things that will give you the perfect glimpse into this beautiful city!

Sometimes, the touristy spots are the best spots β€” I mean, at least when it comes to grabbing those perfect Instagram photos! If you’re planning on grabbing a picture at the Cloud Gate, or as Chicagoans fondly call it, the “Bean,” you’ll want to either head there first thing in the AM or after dark if you want to avoid the crowds.

Millenium Park has so much to offer, no matter what time of year you’re there. In the summertime, take a walk through the Lurie Garden and take in the greenery and florals. If you’re visiting in the colder months? You can enjoy some winter wonderland fun at the ice skating rink.

4. Take an evening stroll around town after dark.

Heading to Chicago soon? Check out these 10 must-do things that will give you the perfect glimpse into this beautiful city!

Chicago is a beautiful city β€” but there’s just something extra magical about strolling the town after dark. Seeing the buildings lit up, as the crowds start to lighten is nothing short of stunning. The city offers such a variety of rich architecture, that it’s worth taking in both day and night. Whether you’re taking a walk through Millenium Park or strolling down by the beach, staying out late is totally worth it!

5. View Chicago from 94 floors above ground.

Heading to Chicago soon? Check out these 10 must-do things that will give you the perfect glimpse into this beautiful city!

This might be my favorite thing that we did during our trip to Chicago β€” I mean, honestly, would you just look at that view?! At the top of the iconic John Hancock building in the heart of the city is 360 Chicago Observation Deck.

I can tell you firsthand that the price of tickets is worth every penny (though I will say to avoid the Tilt Attraction that’s there β€” it’s a bit gimmicky). The 360-degree view of Chicago and Lake Michigan are stunning no matter what time of day you’re there. If there’s one place you should plan on lugging your camera to, it’s here!

6. Spend time exploring Chicago’s neighborhoods.

Heading to Chicago soon? Check out these 10 must-do things that will give you the perfect glimpse into this beautiful city!

Would you judge me if I told you that I spent over an hour and Uber rides across town getting the grand tour of downtown Chicago because I put the wrong address into the app? Because… that definitely happened. 😜 While I wouldn’t suggest going this route to see the city, the neighborhoods around Chicago are totally worth exploring.

We stayed in Lincoln Park, which I immediately fell in love with. It’s only a short ride to the heart of downtownΒ but has all of the views, yummy eats, boutique shops, parks, and vine-covered row houses your little heart could desire. And there are so many other neighborhoods we wanted to get to but didn’t have the chance. If you have a spare few hours, definitely spend some time exploring!

7. Head down to the lake for an afternoon.

Heading to Chicago soon? Check out these 10 must-do things that will give you the perfect glimpse into this beautiful city!Lake Michigan adds so much to the already vibrant cityscape. On the northern side of the city, you can walk right along the beach. This was also, by far, one of my favorite places to grab a few photos. Getting a shot across the water with the city in the background is priceless!Β There is a trail that runs up through Lincoln Park, which is also home to the local zoo and conservatory.

Looking for a little more adventurous view of the lake and city?Β Head over to Navy Pier and jump on the Centennial Wheel!

Where to Eat

8. Cafe Ba-Ba-Reeba!

The name is a bit weird, but man, this place is insanely good! I may or may not have devoured an entire bottle of red wine, but hey, we only live once, right? πŸ˜‰ Cafe Ba-Ba-Reeba! is known for their tapas style and small plates, so you’ll want to order one of everything on the menu β€” and you totally should! Sharing a feast’s worth of plates with a few people is the best way to experience this place.

9. Quartino Ristorante

Through and through β€” I’m Italian. Naturally, I inherited a love for all things Italian food. Which is why I immediately fell in love with Quartino Ristorante. Between the vintage atmosphere and the incredible food, you’ll never want to leave. The pizza is incredible, and so is their variety of charcuterie boards. Oh, and the bread β€” bring on the carbs!

10. Cantina Laredo

If you know me well, then you know just how much I love Mexican food. If you’re anything like me, you’ll love Cantina Laredo! During the warmer months, they open up the dining room to the outdoors so you can enjoy the breeze while you’re eating. It’s a modern, contemporary take on Mexican food, with some of the freshest ingredients I’ve ever had. If you decide to go, get the guac and tacos!

Have you been to Chicago? What are some of your favorite things to do?

You Might Also Like...

  • Victoria Harris

    I love Chicago! We were just there a couple weeks ago. We did the Willis Tower Skydeck and really enjoyed it – glad we skilled the Tilt Attraction at 360Chicago based on your recommendation. I already can’t wait to go back!

  • Kacey

    I have only been to Chicago once and I loved it! Would love to check out some of the things you included in this post! I love the branding of your site by the way!

  • Marlene

    I love the idea of an uber ride around the city! How fun!