Holiday Homes in Central Chicago

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Check prices for these dates

Next weekend
1 Aug - 3 Aug
In two weeks
8 Aug - 10 Aug
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22 Aug - 24 Aug
In two months
19 Sept - 21 Sept

Featured Holiday Homes in Central Chicago

Insta Worthy ^Prime Spot ^Patio ^Parking ^Fireplace
Kitchen features a stainless steel microwave and a window with a decorative grille.

Insta Worthy ^Prime Spot ^Patio ^Parking ^Fireplace

9.2 out of 10, Wonderful, (56)
"Super convenient for Old Town and train station, will stay there again."
Insta Worthy ^Prime Spot ^Patio ^Parking ^Fireplace
Beautiful, Remodeled Penthouse Unit in Old Town!
Enjoy cooking in this fully equipped kitchen with a refrigerator, microwave, oven, and dishwasher.

Beautiful, Remodeled Penthouse Unit in Old Town!

9.4 out of 10, Exceptional, (24)
"Super nice property, and the host was so helpful and kind. Super happy with the house overall, would recommend! "
Beautiful, Remodeled Penthouse Unit in Old Town!
Old Town 3bd 3ba Coach House, Garage Parking Incl by AllSet Turnover
Enjoy cooking in this well-equipped kitchen with a central island, sink, and dining area.

Old Town 3bd 3ba Coach House, Garage Parking Incl by AllSet Turnover

9.2 out of 10, Wonderful, (16)
"Very quiet and close to CTA , Old Town easy access to the city"
Old Town 3bd 3ba Coach House, Garage Parking Incl by AllSet Turnover
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars
Enjoy cooking in the well-equipped kitchen with a large island countertop and sliding door to an outdoor seating area.

Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars

9.4 out of 10, Exceptional, (97)
"Good for our get together."
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars
Gilded Age Gold Coast Mansion with Parking, Deck, Fireplaces
Kitchen features a central island with a granite countertop, stainless steel appliances, and wooden cabinets.

Gilded Age Gold Coast Mansion with Parking, Deck, Fireplaces

10.0 out of 10, Exceptional, (2)
"We had a great stay! Inna provided us all the info we needed to check in smoothly when we arrived and the garage spot made it easy for us to park and unload luggage straight into the house. Everything was super clean! The house is big enough that even with so many guests everyone felt spread out and had their own space. We were able to take a 5ish min walk to the beach which was such a bonus! "
Gilded Age Gold Coast Mansion with Parking, Deck, Fireplaces
Luxury House in the heart of Old Town with Parking
Relax in this stylish living space with a large sofa, glass staircase, and wine rack.

Luxury House in the heart of Old Town with Parking

10.0 out of 10, Exceptional, (50)
"We stayed for a number of weeks at the property - it was an excellent stay! The property is exactly as advertised and the owner was extremely helpful, communicative, and responsive throughout. The house is modern, in good condition, and is an excellent location."
Luxury House in the heart of Old Town with Parking
Secure, Quiet, Solo Traveler's Fave, Free Coffee!
Hotel BNB's entrance welcomes guests with a clear view into the interior.

Secure, Quiet, Solo Traveler's Fave, Free Coffee!

Secure, Quiet, Solo Traveler's Fave, Free Coffee!
Ideal Group Getaway: Prime Location, Parking, Backyard, Sunroom & Pet-Friendly
Relax in this stylish space with a sliding glass door leading to an outdoor area, a comfortable sofa, and a modern kitchen.

Ideal Group Getaway: Prime Location, Parking, Backyard, Sunroom & Pet-Friendly

10.0 out of 10, Exceptional, (3)
"Charming home in the Old Town area. Close to so many great restaurants and bars. Very spacious and clean. Our host Inna was so welcoming and helpful with recommendations!"
Ideal Group Getaway: Prime Location, Parking, Backyard, Sunroom & Pet-Friendly
Family-Friendly South Loop Escape by RedAwning
Enjoy cooking in this well-equipped kitchen with a refrigerator, microwave, and dishwasher.

Family-Friendly South Loop Escape by RedAwning

Family-Friendly South Loop Escape by RedAwning
Modern- Smart Home in Wicker Park
Relax in a serene outdoor space with a sofa, fire pit, and lush green surroundings.

Modern- Smart Home in Wicker Park

Modern- Smart Home in Wicker Park
Elegant 4 br Old Town Home; Private Yard; Parking; Amazing Location
Enjoy cooking in this well-equipped kitchen with a refrigerator, microwave, and oven.

Elegant 4 br Old Town Home; Private Yard; Parking; Amazing Location

9.8 out of 10, Exceptional, (97)
"This was so great for our family of five, with three teens. It’s so convenient to public transportation and easy access to all of the Chicago attractions. This is a wonderful property with everything we could have possibly needed. Our kids loved the third level which is so big it’s like another apartment. We’d love to stay here again on our next visit to Chicago."
Elegant 4 br Old Town Home; Private Yard; Parking; Amazing Location
Cozy Private Room in Prime Downtown Chicago
Hotel BNB's entrance welcomes guests with a sleek glass door and illuminated sign.

Cozy Private Room in Prime Downtown Chicago

Cozy Private Room in Prime Downtown Chicago
Historic luxury townhouse on Chicago's Gold Coast
Relax by the fireplace in this inviting living room, featuring comfortable armchairs and a large window with a view.

Historic luxury townhouse on Chicago's Gold Coast

9.4 out of 10, Exceptional, (71)
" Urban location, access to everything"
Historic luxury townhouse on Chicago's Gold Coast
Secure, Private, Free Wi-Fi and Coffee, Accessible
Enter Hotel BNB through a glass door into a welcoming lobby with a reception desk and comfortable seating.

Secure, Private, Free Wi-Fi and Coffee, Accessible

Secure, Private, Free Wi-Fi and Coffee, Accessible
GROUP LUX in Old Town 4bd/3ba (+Rooftop/Parking)
Enjoy cooking in this well-equipped kitchen with a central island, stainless steel range, and ample counter space.

GROUP LUX in Old Town 4bd/3ba (+Rooftop/Parking)

9.8 out of 10, Exceptional, (23)
"My coworkers and I had a wonderful time at this perfectly located property. The property had plenty of privacy, charming At CB textural character, and was perfectly located for shopping and dining. Would definitely stay here again!"
GROUP LUX in Old Town 4bd/3ba (+Rooftop/Parking)
2 Luxury Queen with Rooftop Lounge & City Views Near Attractions
Property grounds

2 Luxury Queen with Rooftop Lounge & City Views Near Attractions

The price is NZ$1,045
includes taxes & fees
27 July - 28 July
2 Luxury Queen with Rooftop Lounge & City Views Near Attractions
Clean & Modern • Central Location • Free Coffee!
Hotel BNB's inviting entrance welcomes guests with a view into the reception area.

Clean & Modern • Central Location • Free Coffee!

Clean & Modern • Central Location • Free Coffee!
2 Connecting Suites at a 4⭐️ Hotel
Experience the grandeur of our lobby, featuring a central fountain, plush seating, and intricate woodwork.

2 Connecting Suites at a 4⭐️ Hotel

The price is NZ$1,239
includes taxes & fees
18 Aug - 19 Aug
2 Connecting Suites at a 4⭐️ Hotel
Luxury SOHO Styled Two-Level Townhouse - Old Town
Relax in style with a cushioned sofa, a black chair, and a small table, perfect for reading a book.

Luxury SOHO Styled Two-Level Townhouse - Old Town

10.0 out of 10, Exceptional, (15)
"little cold downstairs but overall very nice and clean "
Luxury SOHO Styled Two-Level Townhouse - Old Town
Stunning Condo #2 - Downtown River North!
Enjoy cooking in this well-equipped kitchen with a large island and window overlooking the living area.

Stunning Condo #2 - Downtown River North!

9.6 out of 10, Exceptional, (18)
"Great location and communication"
Stunning Condo #2 - Downtown River North!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Central Chicago Hotel Reviews

River Hotel

River Hotel

10/10 Excellent
"A"
Patrick 2-night trip
Posted 9 hours ago
River Hotel