Ah, The Windy City! When you step foot in vibrant Chicago, expect to be under its spell for a long, long time–especially if you’re a lover of art and a lover in general. Some movies that were shot here include classic, swoon-worthy rom-coms such as While You Were Sleeping and My Best Friend’s Wedding. So, you and your significant other can check out some of the shoot locations and maybe recreate a scene or two!
What’s special about Chicago is that it also boasts a rich history and contemporary offerings. It has everything for everyone, including enjoying an intimate spa experience at AIRE Ancient Baths Chicago or relishing drinks and sunset views at the lofty CloudBar at 360 Chicago.
What are you waiting for? Plan your itinerary now and book any of the best romantic Airbnbs in Chicago, Illinois, for an amazing experience.
We’ve also compiled a couple of fun activities for you and your beloved to try out:
Tours and activities for couples:
- Take gorgeous photos, learn interesting historical facts, and listen to amazing romantic stories on a walking tour of Chicago.
- If you are looking for something more laid-back while still boasting a romantic atmosphere, book a Lake Michigan cruise. There's even a bar onboard if you'd like to toast to each other.
We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and access to romantic amenities and activities. The image galleries get refreshed with the latest updates regularly. They were last updated on October 30, 2025.
1. Skyline Oasis (from USD 3060)
One of the things I would look for in an Airbnb for a romantic retreat is beautiful views, and Skyline Oasis provides just that! You can admire the lake and city from the balcony or simply through the floor-to-ceiling windows as you and your lover drink some wine.
While here, you can use any of the available building amenities, such as a shared hot tub where you can go for some R&R together. But if you need something just for you two, a private sauna is also available and is the perfect place for intimate conversations as you relax with your partner.
And if you’re looking for date ideas, why not take your beloved for a delicious meal at a nearby Michelin-starred restaurant or explore museums and nightclubs in the vicinity?
Chicago, Illinois, United StatesSuperhost
Accommodates: 2
2. Luxurious condo with pool access (from USD 296)
Visiting Chicago during the summer? If so, you can book this luxurious condo downtown! Apart from its great location, this rental is perfect for couples because it boasts a lovely queen-size bed and a full bath. What also lured me was the hanging swing in the living room. Just imagine softly swinging while you wait for your partner to cook a romantic dinner.
When it’s hot outside, take your partner for a swim in the outdoor pool and cool off together. Meanwhile, cold nights can be made warm thanks to the fire pit that you two can cuddle up next to.
Chicago, Illinois, United StatesAccommodates: 3
3. The Bad Manor (from USD 670)
I love this Airbnb, it oozes a classy vibe through and through as if you’ve traveled back in time. But apart from the decor, The Bad Manor has a queen-size bed, where you can sleep in peace. And, in the morning, prepare breakfast in bed for your beloved in the well-equipped kitchen. As for later meals, you can ask the host for the best restaurants and bars in town for a lovely date.
Both of the two living rooms also match the interior, complete with cozy sofas. So, if you want to cuddle up with your special someone, you can do so easily!
Chicago, Illinois, United StatesAccommodates: 3
Nearby romantic Airbnb
4. Charming treehouse for adventurous couples (from USD 314)
If you and your partner love being surrounded by beautiful nature, then this treehouse will surely charm you into booking it! One of its best features is the private cedar hot tub, where you and your lover can relax for a few hours while chatting away. Alternatively, you can also hang out by the cute koi pond and admire the beautiful fish together or lounge in the hammock as you recall fond memories of your relationship. When it gets late, take some marshmallows out to the fire table or fire pit and have a fun night roasting them.
Before bed, watch a romantic movie on the TV while lounging by the fireplace and wearing robes provided by the hosts!
Schaumburg, Illinois, United StatesAccommodates: 4
Top guest reviews
Host:
daniel was a gracious hostagain the host is greatdaniel was a terrific hostdaniel was very accommodating and consideratehe is a great hostLocation:
it’s the perfect distance - not too far but not too close - and so appreciated daniel’s hospitalitythis cute little tree house is such a great place to get away for a few days and relaxgreat place to go to get away from the city plenty of privacythe neighborhood is quiet and peacefulamazing and magical location totally worth doing it onceCleanliness:
very clean and so cozy insidehopefully that can be deep cleaned in the futuredaniel's place was very clean and relaxingthe place was clean bed was so comfortablesuch a magical place to sleep in the treetops the place was beautiful clean and well equippedRead more reviewsAmenities & Room:
had an excellent stay the tree house is very cozy and loved the amenitiesthe loft bed was perfect for our kid and the big bed was super comfyhot tub private outside shower beautiful koi pond grill and several outdoor seating optionsthe garden area with pond hot tub etc was beautiful comfortable and really fun on a cold night
Fall in love all over again in Chicago
The beauty of Chicago is unparalleled, and it is no surprise that it appeals so much to couples. Everything from its various attractions to its stay options can bring back the spark in your relationship. So, when you visit this vibrant city, make sure to choose any of the above Airbnbs for a romantic stay.
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