48 Hours in Chicago

Chicago is an iconic city with so much to offer – even if you’re just visiting for a short period of time. If you’re considering a trip soon (and may or may not have little ones in tow) this fun 48-hour itinerary will help you maximize your time and leave the windy city with some amazing memories. From where to stay, what to eat, and how to truly experience the magic of this booming metropolis… continue reading below! 

After a relaxing, weeklong trip to Minnesota to spend time with family, we decided it would be fun to extend our trip a few more days by taking the kids the Chicago. Scott and I visited Chicago for a few days when I was pregnant with Parker and we had such an incredible experience. I think it’s absolutely possible to sample the best that Chicago has to offer in a short amount of time, as long as you plan your itinerary appropriately. 


We stayed at LondonHouse, located just along the riverwalk and steps away from Michigan Avenue. When we visited Chicago previously, our hotel was about five or six blocks away and we kept finding ourselves right back around the riverwalk. There is just so much excitement in this area – so many things to do and places to eat, and the views are epic.

Staying along the riverwalk was a no-brainer for this trip. Centrally located hotel rooms are more of a priority for us when we travel with the kids too because we don’t want to travel too terribly far for our adventures. And by “we” I mean our kids. Plus, we need a comfortable place for Charlie to nap during the day, and space/accommodations to keep Parker and Brady entertained during the same time. LondonHouse checked all of these boxes for us and the views did not disappoint.

Booking Tip: When you check in, be sure to ask if you have a room with a view. If you don’t, they’ll get you one! It may be slightly smaller, but trust me, it will be so worth it. The kids spent hours playing by the window watching taxis, boats, and people walk around the riverwalk.


There is so much to do and see in Chicago any time of year! For this trip, we arrived the first week of October and were thankful to have such beautiful weather. When it’s warm, you can spend almost all of your time outdoors, and when it’s cold, there are endless activities to do indoors – like museum tours, subway rides, comedy shows, baking classes, and more. Our last trip was in mid-December and we stayed just as busy as we did this time around.

Because this trip just so happened to take place in the middle of a global pandemic, several precautionary measures were clearly in place. When planning a trip to Chicago (or anywhere, really) during this time, start by checking with all of the places you plan to visit to make sure they will be open. Several places here were only operating a few days a week and others were closed to the public altogether, including the Navy Pier. Before we arrived in Chicago, I made sure to have all of our attractions booked and pre-paid.

Wendella Sunset Architecture Boat Tour

You can’t visit Chicago without doing a boat tour! We chose Wendella’s Lake Michigan Sunset Cruise but because the winds were too high in the lake, it turned into a modified River Architecture Tour (which stays just in the river). Wendella provides several tour options throughout each day so you’ll certainly be able to find one that works best with your schedule. However, I highly recommend a sunset tour because you get to see the city at its most beautiful hour.

Each boat has a snack and drink bar below deck which we took full advantage of, and they play classic music as you cruise. Scott and I had a good ‘ol time drinking beer and dancing around with the kids as we coasted in between the beautiful skyline. It was definitely a highlight of the trip. If you ask Brady, he’ll tell you it was his favorite part.

SkyDeck at Willis Tower

Another must-see while in Chicago is SkyDeck, and if you’re not too afraid of heights, The Ledge. This breathtaking observation area is located at the top of the Willis Tower and offers spectacular views of four states. The Ledge is a large glass balcony that extends four feet outside the 103rd floor of Willis Tower. My tip for making it out there is to just not look down.

If you ask me, I’d say any time of day is a good time to visit SkyDeck. However, you really can’t beat the sunset views.

Cloud Gate (The Bean)

Seeing Cloud Gate, aka The Bean, without people around it was quite a rare sight. As part of Millennium Park’s Covid precautions, a gate was set up around the entire installation. The silver lining is that you can capture unobstructed shots of The Bean itself, which would otherwise be pretty impossible.

The entrance to Millennium Park is always guarded by law enforcement, however, you can freely walk in and out at no charge. Be sure to stop and take in all of the flowers and greenery throughout the park – perfect photo ops for social media!

North Avenue Beach

North Avenue Beach is one of the best spots to stop and truly take in the gorgeous Chicago skyline. The kids loved playing in the sand and spent most of their time searching for Sea Glass. To my surprise, they each found a handful of beautifully colored pieces that now sit in a jar on my dresser.

Several beachfront eateries and bars sit along North Avenue Beach, including the Shore Club and Castaways, making this area a worthwhile day trip when the temperatures are right.

Other things to do while you’re in town:
  • Scavenger Hunt at the Field Museum
  • Comedy Clubs (We loved the Laugh Factory – many SNL greats were discovered here)
  • Garfield Park Conservatory
  • Shedd Aquarium

Pro Tip: Parking is expensive in Chicago. Like, really expensive. If you drive to the city, valet your car and keep it there. Then, whether you fly in or drive, invest in a 1-day, 3-day, or 7-day CTA Pass. This gives you unlimited subway and bus rides. Chicago has a fantastic and efficient public transportation system, and riding a subway through the city is something you have to experience!


One of my favorite things to do on a trip is eat. It’s also one of the first things I start researching whenever we’re planning to visit a new city. What can I say… I live to eat. And because Chicago is such an incredible mecca of culture, history, and abundance, the food options are some of the best in the country. Don’t even get me started on the deep dish pizza.


Beatnik is a super eclectic and totally unique spot for delicious drinks and festive faire. They have two locations in the Downtown Chicago area – both magnificent in their own right. We stopped at the Beatnik “On the River” location just before checking into our hotel and it was a perfect introduction to the city. We watched tour boats glide by as we sipped some of the best drinks I’ve ever had in my life – try the Nakama Spritz AND their featured Slushy of the month.

The Beatnik “West Town” location is even more of a photographer’s dream with tropical plants and festive decor covering every inch of the restaurant. Did I mention their food is amazing too?


If you like to explore cities more like a local and less like a tourist, this is a spot for you. Herb-N-Juice serves organic cold-pressed juices, smoothies, and wellness shots, and they just so happen to be located in a hidden alleyway in Lincoln Park. Their green juice is incredible (and I’m a bit of a green juice snob) and they come in glass bottles that you can keep forever. Another plus: Beacon Doughnuts is right next door – and I’m all about a balanced diet.

Address: 810 W Armitage Ave, Chicago, IL 60614

How did I find this spot? Let me explain. Before we embark on road trips, I always make a ton of homemade green juices for the road. They always make me feel better as we travel and give me peace of mind knowing the kids are still getting good nutrients when we’re far away from home. So when we run out of our stash, I always seek out the best spot in whatever city we’re in. My research in the Chicago area led us here and I’m so glad it did!

Stan’s Donuts

If you’ve ever been to Chicago, chances are you’ve heard of Stan’s Donuts. With locations all across the Chicago area, this is clearly one of the most popular donut shops around. On our last morning in the city, we walked to one that was about two or three blocks from LondonHouse and let the kids choose a dozen. This is our favorite thing to do when we get donuts. We never eat just one – instead, we all take little pieces of each so we can try everything.

The Stan’s Donuts location in Wicker Park is the best for photo ops. The interior is bright pink and the exterior is perfect for a wide shot!

Goddess and the Baker

Goddess and the Baker is another Chicago staple that I would choose for every meal if I had the chance. They have locations spread out throughout the city, so you’re sure to find one close to where you are. We’ve always stopped by for breakfast and coffee, but they also have a great lunch menu as well as an array of fresh bakery items, like scones, croissants, iced cookies, macarons, and more. My favorite location is along Wabash Ave., just west of Millennium Park. It has great views of the subway (bottom left photo) and it’s never too busy.

Address: 33 S Wabash Ave, Chicago, IL 60603

Maison Marcel

Maison Marcel is a chic French bakery in the Lakeview neighborhood. We stopped here for a late brunch the day we arrived and didn’t leave a single crumb behind. In additional to a yummy brunch menu, they also serve green juices and smoothies, and have an adorable bar in the back with where they serve their own wine. Don’t leave without getting a freshly baked croissant and macarons!

Address: 3114 N Broadway, Chicago, IL 60657

The Hampton Social

Hampton Social is known for its Instagram-famous photo ops and a signature Rosé. While these were two main reasons I wanted to go, I was absolutely blown away by their yummy coastal cuisine. The lobster roll and caesar salad were divine. Hampton Social has two locations in Chicago, but you’ll want to visit the River North location (on Hubbard Street) for the best pictures.

We stopped here for an early dinner (about 4:30 pm) before our boat ride and there were probably two or three other tables in the entire place. It was the perfect time to go for a quick photo and meal.

Other Spots to Visit:

If you’re looking for the best deep dish pizza in Chicago, there are two places I’d recommend: Giordano’s and Gino’s East. We went to Gino’s East on our last trip and Giordono’s on this trip, and to be honest, they’re both incredible. However, I will say that we now have frozen pizzas shipped directly to us from Giordono’s every other month. Do with that information what you will.

Elaine’s Coffee Call is an adorable spot located just a few blocks away from North Avenue Beach. While we didn’t make it in time to grab a drink before they closed, their Almond Lattes come highly recommended.

  • Magnolia Bakery (best cupcakes)
  • Jeni’s Ice Cream in Wicker Park
  • BomboBar


A nudging factor to extend our trip to Chicago for a few days was the fact that we’d be able to celebrate Charlie’s 2nd birthday somewhere fun. And that’s exactly what we did! Our last morning in Chicago, we picked up some balloons at a local party store and walked to a few iconic spots to take photos. Several people who walked by us wished Charlie a happy birthday and he couldn’t stop smiling. He felt like such a big boy!

Chicago is always such a treat. The people are so nice, the city is so safe, and we always leave with the best memories. We look forward to going back again soon!

Questions about Chicago? Let me know in the comments below!

Stay tuned for our next adventure.

xoxo Jen

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