48 Hours in Chicago – How to Make the Most Out of Your Trip.

After recently getting back from a long weekend trip to Chicago, I wanted to share all about it with you. However, I thought I’d put together a little guide of some of my favorite things to do, so that you can see just how many incredible things you can fit into a short time in a city. Josh and I got pretty skilled at maximizing our time in a city after we visited seven cities in three weeks last March during our spring break.

This was one of my favorite trips to Chicago to date because 1) my dad gave this trip to me as a belated Christmas present, so I was well equipped with some shopping money for a fun time exploring Michigan Ave. and 2) Josh was able to join us, so I was really happy he could spend a weekend hanging out with my family.

We took the train, which is my absolute favorite way to get to Chicago. The Amtrak is a quick and easy way to travel, and the student discount is pretty great, too. Early last Friday morning, we all begrudgingly pulled ourselves out of our beds and left on an early morning train to Chicago that brought us to Chicago’s Union Station around 10:30am.

From there we took a taxi to our hotel and our weekend began! Below I’ve created an itinerary using most of the things we did this trip, along with a few of my all-time favorite things to do in Chicago, so that you can have a fun-filled, jam-packed 48 hour itinerary in Chicago! Sometimes for me, it’s really helpful to see how you can accomplish all kinds of things in such a small amount of time, so without further ado, here is my Guide to 48 Hours in Chi-town!

Friday, after a late morning arrival in Chicago

12:30pm – Arrive at the hotel on Michigan Avenue, the InterContinental Chicago. I would highly recommend staying here, since I’ve been here on three separate occasions and loved every time. It even has a Starbucks connected to the lobby.

After we checked in to the hotel and organized our things, we headed downstairs, grabbed a coffee from Starbucks and hit Michigan Ave. 

1:45pm – After perusing around some stores on Michigan Ave., it’s time to eat! Opt for the Grand Lux Cafe, which is operated by the same owners of one of my all time favorite restaurants, The Cheesecake Factory.

3:00pm – Hit the town! You’re right in the middle of Michigan Ave., so it’s time to shop! This past trip, I hit LUSH, Topshop, Free People, Nike, ZARA, and a few other places. Since I rarely get the opportunity to shop Michigan Ave., I always go a little crazy shopping when I do come here.

6:00pm – Head towards probably the cutest restaurant I’ve ever been to in my entire life, The Hampton Social, home to the famous “rose all day” sign you’ve most likely seen on Instagram before.

8:00pm – After an incredible dinner at the Hampton Social, head back to the hotel and change into some more comfortable clothes. Walk from the hotel to Lucky Strike, where the rest of the evening can be spent bowling, playing pool or ping pong, and munching on appetizers if you’re still hungry. This place has been a staple to every Chicago trip I’ve taken with my family. It’s the nicest bowling alley I’ve ever been to, and it’s always super crowded, which just adds to the fun atmosphere.

10:30pm – You’ll be pretty tuckered out after your big day, so head back to the hotel to get some sleep. You can always stream a movie in bed, but after this long of a day, I’m sure you’ll be ready to fall asleep as soon as possible.


8:30am – Wake up and get ready for another big day. Today is a big day for photos, so make sure you’re looking ready for a bunch of photo opps!

9:30am – Catch a taxi and head to Goddess and the Baker for breakfast. This is honestly one of my favorite coffee shops and bakeries in the entire world, and it’s a must-do if you’re looking for a fun breakfast spot downtown Chicago. Filled to the brim with the perfect mid-century modern decor, Goddess and the Baker offers food all day, but I would personally recommend the acai bowl, jasmine tea, and apple cinnamon sugar scone for breakfast. It’s a game changer!

3:00pm – Head to Millennium Park to explore! There’s so much to do there, that it will easily take you a while to see everything there is to do. From the stereotypical pictures in front of the Bean or {if you happen to visit in the wintertime like I did} ice skating in front of the Bean, there are so many fun things to do!

6:00pm – Walk back across the Michigan Avenue Bridge to the hotel, where you can have some down time and time to get ready. You’ll need a fancy outfit for what’s to come tonight.

7:30pm – Catch a cab to the Willis Tower to the swanky Metropolitan Club restaurant. I would highly recommend the chicken stuffed with goat cheese and dried cranberries. The views from this restaurant are absolutely incredible. To be able to

10:30pm – After staring at the views of the city from your table, it’s time to head back to the hotel. Make sure to get your things semi organized because you’ll need to check out in the morning!


9:30am – After all your luggage is packed up, bring it downstairs to the luggage check so you can keep it at the hotel past the check out time!

10:30am – Walk across the street to the Corner Bakery. This is a great place to grab a quick bowl of fruit or a breakfast panini! You’re going to want to make the most of your time today, since today is the day you head home, so you don’t want to waste a lot of time on food!

11:00am – Catch a taxi to the Field Museum! You could spend as little or as much time as you want here, because you could be content visiting one exhibit, or every single one. Your ticket also includes a movie so that takes up time, too! When we went last weekend, we chose to see the movie “Mysteries of China” which was such an interesting movie in 3D! Also, there was an incredible tattoo exhibit featured where a tattoo artist was actually giving tattoos inside the museum. I could honestly visit the Field Museum every single time I come to Chicago because I learn so much every time. It’s definitely on my must-do list for anyone’s trip to Chicago.

Our train was at 5pm, so we got back to the hotel around 3pm, grabbed some coffee and our luggage, and headed to the train station. 

And with that, a fun weekend in Chicago is pretty much summed up! I wanted to highlight some of my favorite aspects of Chicago for you in case you have a trip planned there soon! Or, if you’ve already visited Chicago, what are some of your favorite things to do there? I’m always looking for more recommendations because I’m sure I’ll be heading back in the near future.



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