Sometimes the closer we live to a destination, the less we see it as an option for a getaway. It might feel less special or feel like a pointless way to spend money when your home is nearby. But for any of you who live in the greater Chicagoland area (like me), a Chicago staycation should not be overlooked.
A few months back, I was feeling like I needed to treat myself but I couldn’t decide where to go. Nothing was seeming to line up (a trip to Asheville, NC, or a Florida Keys road trip were the competing options). Then I realized I have Chicago in my backyard and that my bucket list for the city was getting a bit long, so I decided to book a Chicago staycation! It immediately felt like the best decision.
Chicago Overview
If you found this article, you probably live close to the city and know a lot already, so I won’t go into too much detail here. I just want to remind you how amazing Chicago is and how much there is to explore. Its nicknames alone show how many layers there are to its history and personality. Do you know why Chicago is called “The Windy City” or “Second City?” Did you know that the world’s first Ferris Wheel was built in Chicago in the 1890s to rival the Eiffel Tower?
From architecture to sports to food, you will not run out of things to do and learn in this world class city of almost 3 million people. However, this is not a comprehensive guide to Chicago. In this post, I will highlight things I did on my most recent visit when I wanted to treat myself and recharge. I went alone to focus on relaxation and then sprinkled in some long walks and a bit of learning.
What to do During Your Chicago Staycation
I did this Chicago staycation solo, but I also think this itinerary would be great for couples wanting a low-key, romantic getaway or for those who can’t spare much time to fly somewhere for a vacation. Before I get into all the details, here’s a map to give you an idea of where everything is!
AIRE Ancient Baths
This went straight to #1 on my Chicago bucket list the moment I heard about it. I didn’t get any photos because cameras aren’t allowed inside, so I’ll do my best to explain what it was like (and you can see photos on their website linked below).
AIRE Ancient Baths is a beautiful spa/bath house located in a restored 1902 factory near the West Loop. The tradition of public baths as part of society dates back to Roman times, although there’s evidence of bath houses even older than that. (This article is really interesting if you want to read more about bath house culture.) From Turkish hammams to Japanese onsens and everything in between around the globe, AIRE Ancient Baths has now brought the public bath right here to Chicago. (But don’t worry, there’s no nudity.)
When planning a Chicago staycation with relaxation as my top priority, I couldn’t wait to spend 90 minutes dipping into all the baths on offer. I also splurged and booked a massage which was fantastic. AIRE’s tagline is “a journey of sensations,” which is exactly how I would describe my experience. There were so many sensory options to explore– a bath with tons of jets, an extremely hot bath, an outdoor bath with a waterfall, a zero gravity salt bath, a bath with music playing underwater, and even icey plunge pools. There was also a large section of hot stone you could lay on while sipping complimentary tea and juice. I seriously cannot wait to go back–it was incredible and worth every penny!
Architecture Cruise
Chicago is such a gorgeous city, and one of the best ways to appreciate the view is to book a river cruise and learn a bit about its architecture and history. It’s definitely touristy but should not be missed–even for locals!
There are many operators but I went with https://architecturetourchicago.com/ during my Chicago staycation and would recommend them.
Did you know that Willis Tower (formerly Sears Tower) is the 23rd tallest building in the world? Or that Chicago’s 3rd tallest building (the St. Regis) is the tallest building in the world designed by a female architect? There are so many fun facts to learn and interesting structures to see while you cruise along the Chicago River (which is also the only river in the world that flows backwards.) See, the facts just keep coming!
Relax at your Bed and Breakfast
I will go into great detail below about where I stayed (it was sooo dreamy), but during a relaxing Chicago staycation you should definitely leave yourself time to savor breakfast and coffee each morning and binge Netflix each night. Talk about feeling recharged!
Chicago Staycation: Carve Out Some Time to Read
One of life’s simple pleasures is sipping good coffee while reading a good book–a perfect activity for a weekend of treating yo’self. If you’re looking for a recommendation, “The Devil in the White City” by Erik Larsen is one of my favorites. It’s about the production of the Chicago World’s Fair of 1893 and how a serial killer used the fair to lure his victims. It reads like a novel but is based on real events. Reading about Chicago’s fascinating history while you’re there will make your stay extra special.
Go On A Long Walk
Taking a long walk on your Chicago staycation is a great way to slow down and take in the sights. I always seek out street art when I travel, so I knew I had to walk by the Hubbard Street Murals during this stay. I absolutely loved strolling past all the art (it’s a perfect activity for solo travelers)! You can also walk along the river if you’re feeling inspired by the architecture cruise. Or you can walk The 606, Chicago’s version of The High Line in NYC.
Get Sushi
I don’t get sushi often, so it always feels like a treat when I do. And it’s a perfect dining option for anyone doing this Chicago staycation solo. I went to Sushi-San and thought it was delicious!
Indulge in Dessert During Your Chicago Staycation
Nothing screams treat yo’self like ordering dessert! I had a late lunch the first night of my stay and wasn’t hungry enough for dinner, but I went out just to order dessert. Then I came back to the BnB and watched Netflix while soaking in the tub–it was truly fabulous. I went to Parlor Pizza Bar and ordered a TACOlato. The couple next to me saw it come out and had to order one too haha! I wish I was hungry enough for dinner because I heard the pizza here is good.
Grab a Fancy Drink
I didn’t hit any bars on this trip due to COVID (and I’m not drinking much anymore), but I did want to share these amazing spots if you’re looking to treat yourself to a drink with a fabulous view.
- The Signature Lounge: This is probably my favorite spot because it’s at the top of the Hancock Building with incredible views of the whole city.
- Cindy’s: This bar has an outdoor rooftop section that overlooks Millennium Park. Super vibey in the summer.
- London House: I have not been yet but it’s on my bucket list because it’s right on the Chicago River in the heart of the city.
Go to a Museum or See a Show
COVID prevented me from doing either of these things, but I still wanted to mention them. If you’re planning a solo Chicago staycation and need ideas for what to do alone, you can’t go wrong visiting a museum or seeing a Broadway show. In terms of museums, there are endless options, but the aquarium is high on my list right now. There’s also the immersive Van Gogh exhibit in town.
Chicago Staycation: Where’s Even Worth Staying?
When planning this trip, I knew I wanted to spend a lot of time relaxing. I wanted to stay somewhere with a bit of a wow factor since I’d be spending more time there than usual (compared to a more adventurous trip where I’d barely be at my accommodation). I wanted to treat myself and splurge on a nice hotel for once, so I searched for luxury hotels in Chicago as well as boutique hotels.
When I came across Publishing House Bed and Breakfast I was immediately sold. I mean look at that bathroom! I was so excited to spend 2 nights actually enjoying the room. One night I took a long bath, the next a long shower. I sat on the couch reading and laid in bed watching Netflix. It was divine.
Publishing House Bed and Breakfast is my top hotel recommendation for a Chicago staycation
Since it’s a bed and breakfast, breakfast is included in the rate. Side note: the rates weren’t as high as I thought they’d be for how special this place is. Breakfast is served in the beautiful common area, and it’s different each day. To start, they have a spread of yogurt and fruit and pastries as they serve you coffee in your own french press. Then you get to choose between 2 homemade options for your main plate, made fresh after you order. I absolutely loved the breakfasts I had both mornings. It’s a huge reason why I can’t wait to go back for another stay.
In terms of location, it’s in the West Loop near Fulton Market which has soooo many amazing dining options. The BnB is owned/ run by women which is another thing I love about it. I spoke to one of the owners at breakfast and she was so helpful giving me recommendations for the area. They did such an incredible job designing the whole place and the decor really adds to the experience. I highly highly recommend staying here during your Chicago staycation if you can!
Conclusion
I hope this post gave you some great ideas for what to do and where to stay if you book a Chicago staycation. I truly had the best time on this relaxing trip and fell so much more in love with Chicago in the process. Let me know if you have any questions, but definitely make sure you don’t miss AIRE Ancient Baths and Publishing House Bed and Breakfast! Chicago has so much to offer, but remember that this is not a comprehensive guide. It’s just what I would recommend if you want to do something nice for yourself close to home 🙂
If you liked this post you will probably like this one, where I share my experience staying at a private onsen in Japan!
Staying at Beniya Mukayu: Culture and Luxury Combined
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