Nestled on Lake Michigan, Chicago is a highly urbanized metropolis with a dramatic cityscape. Here, you will get lost in views of busy skylines dotted with towering buildings. One of the most iconic skyscrapers in the city is the 100-story John Hancock Center, which offers an observation deck (among other things), where you can immerse yourself in picture-perfect panoramic city views. Chicago also has a jazz heritage that excites social butterflies, and must-try gastronomic fares such as Chicago-style hot dogs and pizza. With a city as vibrant as Chicago, you might want to make your visit even more worthwhile. You can guarantee yourself a hassle-free and comfortable stay if you choose the perfect accommodation. To give you an idea, browse through this list of the best vacation rentals in Chicago, Illinois.
We handpicked these listings carefully, considering (wherever possible) Superhost status. recent guest reviews, location, accommodation type, prices, availability of dates, decor, and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on November 24, 2023.
1. Modern designer home (from USD 1377)
Still on the fence about your Chicago holiday home? This modern four-bedroom designer home in the Riverwest neighborhood might seal the deal. Close to shops, eateries, and public transport, this Vrbo is very tourist-friendly. Laid out in this five-story space, other than the bedrooms, are four baths, a living room, indoor and outdoor dining, and a state-of-the-art kitchen that excites culinary enthusiasts. Air-conditioning appliances, barbecue essentials, and WiFi are also at your disposal.
Top guest reviews
Amenities & Room:
we made use of the couch the sofa beds and the four beds to fit all comfortablythe mattresses were very comfortablei was also a fan of the concrete floors the square table which easily seated 8nicely decorated spacious great room and kitchen deck upstairswe enjoyed breakfast twice at nearby staxCleanliness:
it was very clean and absolutely beautifulplace was very clean spacious and beautifully decoratedgreat space clean and spacious great kitchenthe beds were very comfortable and everything was very cleanthe place is well decorated and cleanHost:
the host was kind and responsiveexcellent owners really a refreshing experiencethe owner is very accessible and responsivethe owners were very friendly and communicated with us throughout our staya real bonus was the personal attentiveness and hospitality provided by the owner cary colesRead more reviewsLocation:
location is great - a quick walk to some very cute neighborhood restaurantsthe location provided easy access to the central city areagreat location for a weekend in chicagothe location is great with ample parkingwalkable to great restaurants
2. Charming loft-like space (from USD 100)
This vacation rental is set in the trendy West Town, known for its abundance of New American restaurants and hangout nooks. A short walk away from the property, you’ll find a bus stop that’s convenient for tourists with no vehicles. On the other hand, car travelers can take advantage of the free parking space in the garage.
Upon entry, you will be greeted by a sunny open-plan design, which creates a cozy atmosphere that guests enjoy. Two bedrooms and one-and-a-half baths are laid-out inside, which makes it comfortable for four.
Top guest reviews
Amenities & Room:
the apartment itself is open bright and spacious with beautiful views of the cityvery cool comfortable and warm condothe rain kept us in-which was delightful with the fireplace and spacious apartmentbeautiful and comfortable space to meet our daughter and her friend for a show and relaxationenough space for us to relax catch up and do comfortable highly recommendCleanliness:
it is clean classy and comfortableHost:
leina and marii were great hostsgreat appartment and great host would definitely stay again if i was looking to stay in chicagoRead more reviewsLocation:
a great neighborhood with restaurants and a major grocery store (mariano's) close bystaying in their location was perfectthere are so many great bars and restaurants within a walking distance toothis charming third story walk-up was the perfect respite from the cold chicago weather
3. The Dickens Place (from USD 141)
Instagram-savvy tourists will not be disappointed by this sophisticated two-bedroom townhouse. It exudes class and elegance, resonated by its neutral-colored walls, luxurious rustic fittings, granite countertops, chandelier lighting, and sleek selection of appliances. Here, you’ll feel like you’re living in a high-end hotel without the crowds. Kids and pets are welcome, which makes this abode a great fit for families. Top-visited attractions, such as Wrigley Field, United Center, and Union Station, are within a 5 mi (8 km) radius.
Top guest reviews
Cleanliness:
the place was clean and comfortablethe apartment was nice and cleanif the place was cleaned up and attended to it would be a nice place to staythe apartment is clean and located within a mile or so of the blue line trainHost:
the host was helpful and responsivealex is a very responsive & nice hostexcellent property and very responsive owneralex is extremely responsive and was helpful in answering our questionsRead more reviewsLocation:
great place in a great locationthe location was perfect there was plenty of entertainment and dining areas within walking distancegreat location and excellent set-upthey have a fantastic place in a really cool neighborhoodthis was a nice place to stay for a few days in the city
4. Fully equipped retreat near downtown (from USD 197)
Situated 15 minutes from downtown, this recently remodeled accommodation is convenient for tourists in the city. Apart from its location, it pleases patrons with its fully furnished concept, including a kitchen with modern appliances and granite countertops. Plus, this three-bedroom rental is spacious enough for a group of eight, and kids are welcome as well. WiFi is available for guests’ added convenience.
Top guest reviews
Cleanliness:
house was very nice and cleaneverything was nice & cleanit was very clean and actually had a fresh paint job which adds a flare to the propertythis house was everything that i expected it was very nice & cleanRead more reviewsHost:
owner was nice and helpfulthe host was so understanding & the communication skills were excellent will definitely be staying againlinnie is a great host
5. Stylish five-bedroom retreat in downtown (from USD 712)
This vacation rental is found in downtown Chicago, close to many local attractions, including entertainment, dining, and shopping spots. It showcases a quaint brick exterior and a surprisingly modern interior, thanks to its recent renovations. From the sophisticated kitchen and dining area to the chic living space, every corner of this five-bedroom retreat deserves a snap on your Gram. Besides cozy living areas, it offers a tranquil balcony, which is the perfect spot for guests to unwind.
Top guest reviews
Amenities & Room:
the house comes equipped with many amnemities to ensure a comfortable stayplenty of room for our family to spread out and relaxthe rooms were nicely furnished and decorated with great beddingthe kitchen is fully stocked just like the rest of the house with everything that you could possibly needit was a very comfortable and nice place to stayCleanliness:
very clean and well appointedthis place was immaculately clean and beautifully decoratedthe interiors were spotless and the well-equipped bathrooms and kitchen were pinterest worthyclean well stocked warm and perfect for our large familygood space good kitchen cleanHost:
the owner was super easy to communicate withthe owner was very communicative and provided clear entry/exit instructionsour host was very attentive and responsive to our inquiriesthe host was proactive and made sure we had everything we needed for a smooth checkinerik was a great host - very helpful and accommodatingRead more reviewsLocation:
location worked out good tothe location was great as wellthe location and neighborhood were perfectgreat house in a good locationeasy walk to great restaurants and centrally located to access all chicago has to offer
6. Luxury two-bedroom house (from USD 720)
If your trip to Chicago is for a long holiday or business trip, you might be interested in this beautiful two-bedroom rental opposite Hotel Zachary. What makes it the perfect home base for you is that it is fully furnished, can fit six, and offers discounts for long-term stays. Plus, if you’re vacationing with friends, you can split the cost and save more bucks.
WiFi is free, parking is available, and public transport is within walking distance. What more can you ask for?
Top guest reviews
Amenities & Room:
the beds are very comfortableThe condo was so comfortable for the four of usthe parking always able to park in front of the house with the supplied parking permitsThe only negatives are the seals on the windows are not tight and the cold air blows in making it it colder in the rooms Also bring your own coffee as the filters are there with no coffee for the ...a hotel is to have access to a kitchen - and it was ThanksgivingCleanliness:
The kitchen and bathrooms are top quality and super clean AndThe place was incredibly cleanLocation was awesome and the rental was clean and updated nicelyWe enjoyed the property and was very clean and comfortablethe location and building are very very quiet - which is not always the case in Chicago as you can end up having the el train by your back windowHost:
The property owner was very pleasant and helpful even with getting extra parking passesso the rental owner hooked us up with someone named Chuck-so fixing food was a high priorityThe owner even gave us parking passes for our carThe rental owner did offer us a closed in spot prior to the game-Read more reviewsLocation:
The brownstone unit is just a street away from Wrigley and lots of bars restaurants and shoppingThe house is in a great location to walk to the gamesWe were within walking distance to many shops restaurants and barsThe house and location is greatThis location is close to not just the stadium but all kinds of great spots bars and restaurants
7. Superb three-bedroom guest house (from USD 386)
Daydreaming of a blissful holiday in the beautiful city of Chicago? Make it a reality and book this bright and spotless Airbnb, conveniently close to everything that the city has to offer. Nestled in the Sono district, it is a stone’s throw away from points of interest, such as The Mag Mile, Millennium Park, and Navy Pier.
In terms of amenities, this three-bedroom townhouse has two full baths, an open kitchen, a living room with a Smart TV, and laundry appliances. WiFi is also a welcome bonus.
Top guest reviews
Amenities & Room:
The kitchen isn't done justice in the pictures onlineVery spacious with plenty of roomThe beds were comfortable and plenty of hot waterThe condo had lots of space and was very comfortableWe could not believe the size of the kitchen-Host:
Our host was very responsiveimprove theater Owner had great recommendations for things to doAll her helpful suggestions for area attractions restaurantsSpacious immaculate and well equippedThe property was huge extremely clean and well appointedRead more reviewsLocation:
A short Uber into the city for site seeing andThere were plenty of restaurants and grocery stores within walking distancethe Magic Factory was a great location with groceries and restaurants within walking distance5 min walk away Close to IOThe location was perfect too Easy parking and close to everything
8. Fully furnished abode in Avondale
This three-bedroom townhouse is perfect for millennials as it is in the hip and vibrant Avondale neighborhood, where restaurants and nightspots are scattered everywhere. After a day of food trips or a night of bar-hopping, you can come home to this fully furnished rental that you can share with seven of your best buds. Pets are also welcome.
If you fancy dining in and surprising your buddies with your culinary specialties, you can utilize the kitchen, which is complete with appliances and utensils.
Accommodates: 8
Minimum Nights: 2
Refund Policy : 100% refund if you cancel at least 60 days before check-in.
Top guest reviews
Amenities & Room:
kitchen was well equipped too and my most favorite was having the keurig coffee maker and keurig podsvery comfortable and relaxing plus the location is manageable minutes from all of chicago’s amenitieswe loved it we had 5 adults and were comfortableCleanliness:
the property was nice and cleanit was clean spacious everything we need are already therethe property was clean and relaxed with all the essentials needed for cooking and cleaningHost:
he was very helpful and informativejedidiah was very accommodating and friendlyjedediah was a great host and was very accommodating with our late check in due to car problemsjedidiah was very responsive and helpfuljedidiah was fast to respond and really helpful before and during the stayRead more reviewsLocation:
fairly easy access to transportation and walking distance to some nice places to shop and eatit’s central to everything and you will feel welcome and comfythe location is convenient to everything chicago stay here and you won't be disappointedjedidiah's property was the perfect location and size for a weekend getaway with friendsgreat stay and nice and close to the college where we needed to be
9. Family-friendly holiday haven
For tourists who prefer accommodations slightly away from the hustle and bustle of the city center, the Roscoe Village neighborhood is the perfect fit for you. It is trendy, quiet, and family-friendly, and it is located a short drive away from downtown.
There are plenty of cafes and pubs nearby, but if you want to save some bucks on food, you can make the most of the majestic kitchen with granite countertops. Also, you’ll appreciate the sparkling clean bathroom with a walk-in shower, and the patio, where you can enjoy morning coffee in peace.
Accommodates: 4
Minimum Nights: 3
Refund Policy : 100% refund if you cancel at least 14 days before check-in.
Top guest reviews
Amenities & Room:
fresh flowers in all rooms a nice touchthe beds were quite comfortablethe beds were comfortableCleanliness:
it was clean and comfortablesuper clean with comfy bedseverything was clean and homeyapartment was clean and plenty of spacekim’s apartment is delightful every inch was impeccably clean the arrangement is very comfortableHost:
owners very helpful with questionscheckout is easy owner made everything simpleour host was fantastickim was very helpful and accommodatingthe owner kim was very responsive if we had any questionsRead more reviewsLocation:
walking distance to the brown line and several good restaurants within walking distancevery cute walkable neighborhoodgreat location for going to cubs games restaurants and train station close (brown line)great location in the heart of roscoe village on a quiet residential streetfairly easy walking distance to stores and restaurants
Have a wonderful time in Chicago
Chicago is a mecca for tourists, offering diverse attractions from architectural masterpieces to vibrant nightspots. Here, you can spoil yourself with a much-deserved holiday. Make sure to have comfortable accommodation awaiting your return after a fun-filled day (or week) of taking the city by storm.
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