Mixing Work Trips with Friendship Travel

Some trips I take purely for work, and usually those I do alone. But sometimes, I get to take a friend, and that’s always the best way to do a work trip. On my most recent Windy City trip, I got to do just that and bring my oldest friend with me on a Chicago weekend getaway.

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Why This Chicago Weekend Getaway Was a Redo

I’ve visited Chicago before and the visit was… less than stellar. Back in 2019, I got laid off and took advantage of some of the downtime to do a lot of traveling. I took advantage of the Frontier and Spirit midweek last-minute deals and went to as many places as I could in my budget. Unfortunately, I tried to do Chicago on TOO little of a budget, and this may have caused the trip to be less than ideal.

On that trip, I stayed at a hostel, it was cold and rainy, and I was just miserable. The trip deserved a redo, and I got the best possible one. We crammed in as many attractions as we possibly could while also making sure to grab morning coffee, plenty of snacks, and some stunning views.

Travel Logistics and Hotel Stay

The weather held out well for our trip, with only one truly rainy evening (it made for some fantastic views at 360 Chicago). We took the redeye in and a late evening flight back out to maximize our time, with a two-night hotel stay at the Cambria Hotel Chicago Loop.

Disclaimer: With the exception of a few meals, our flight, and our hotel, the majority of the trip was comped for editorial purposes (one of the perks of being a travel editor). I will let you know which parts I paid for and as usual, all opinions are my own!

Important Hotel Safety Note: Chicago Bed Bug Concerns

Now, just a heads up—Chicago seems to be having a major bed bug problem. So many of the properties we researched had recent bed bug issues, so we picked one of the only hotels we could find in our budget that was not having any problems.

We actually liked our hotel; the location was perfect, and it was really comfortable and spacious. And no bed bugs!

Why I Always Drop My Bags at the Hotel First

One thing I always do when I travel is drop my bags off at the hotel. Even if they can’t check you in, I’ve never been told the hotel couldn’t hold my bags for me.

There’s nothing worse than dragging your luggage all around the city and being denied entry to museums, restaurants, and attractions (I’m talking to you, Nashville). Even with a suitcase literally the size of a big purse, I was denied (because it had wheels) everywhere except Ole Red (thank you, Blake Shelton).

Daytime Exploring in Chicago

Visiting Cloud Gate (The Bean)

Since it wasn’t raining yet, we made a beeline for Cloud Gate. It was a little dreary, but pretty empty, so we got some great shots.

Stan’s Donuts: A Chicago Must-Visit

After this, we made our way over to Stan’s Donuts (a favorite from my first visit and a spot that was a bit pricey but still worth it) because the pistachio donut is amazing. My friend loved it so much that we went back every single day.

Chicago Architecture Cruise with Shoreline Sightseeing

After this, we headed out on an architecture cruise with Shoreline Sightseeing. This has been on my list for years. The weather cleared up even more, so the cruise was actually quite warm and a lot of fun.

It was cool getting to see the city from the water and getting a new perspective of the huge buildings, too.

Navy Pier, Millennium Wheel & Air Show Views

Our next stop was Navy Pier for a trip on the Centennial Wheel and some smoothies at JoJo’s Shake Bar. It was a great way to cool off, and since there was an air show in town, we got some spectacular views of the planes from the top of the wheel. Quite an experience!

Visiting the Museum of Ice Cream Chicago

One of my favorite spots to visit when I can find one is the Museum of Ice Cream. I’ve been to several over the years, and they’re always unique and a lot of fun (plus there’s ice cream). I love how the locations are often a bit tailored to the corresponding cities but always have the same Instagrammable vibes.

The Chicago location was adorable, and we really enjoyed the bar/lounge area for grabbing some sweet treats amidst exploring the different rooms and samples.

Checking Into Our Hotel & Evening Food Stops

Tallboy Tacos Takeout

Once we were ready to head to the hotel to check into our room, we grabbed some food from Tallboy Tacos to take back to the hotel (this was such a great choice and the food here made such great late-night snacks) before checking in and promptly passing out for a couple of hours (oops).

Garrett Popcorn & Chicago Souvenirs

After a quick stop at Garrett Popcorn (a really amazing spot to pick up a delicious Chicago souvenir), we headed over to Skydeck Chicago to catch the sunset and got there just in time. No joke, this was my favorite souvenir. They have plenty of cool buckets that make a great city gift, but I went with the classic Garrett blue bucket to remind me of the trip!

Visiting Skydeck Chicago & The Ledge

I’m pretty afraid of heights, but this visit was to Skydeck Chicago was beautiful. I definitely recommend trying to get there around sunset—it’ll be fairly busy because it’s gorgeous, but it’s worth it. We even stood out on The Ledge for photos and explored quite a bit.

The abundance of spiders on the outside of the windows was considerably shocking. I had no idea these huge spiders could climb and live that high!

Ending the Night with Chicago Snacks

Since we were still pretty wiped out, we went back to the room to enjoy the snacks we had gotten at Tallboy Tacos, and I desperately resisted opening that tin of Garrett Popcorn (it held up great for the trip home).

Check out days two and three of my Chicago weekend getaway here!