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Vacation Homes in Central Chicago

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!
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, (57)
"Super convenient for Old Town and train station, will stay there again."
Insta Worthy ^Prime Spot ^Patio ^Parking ^Fireplace
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
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, (17)
"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
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)
"We enjoyed our stay great host "
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
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
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
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 ￥80,352
￥108,535 total
includes taxes & fees
Sep 2 - Sep 3
2 Connecting Suites at a 4⭐️ Hotel
Spacious Room with Rooftop Lounge & Scenic Views of Chicago
Property grounds

Spacious Room with Rooftop Lounge & Scenic Views of Chicago

The price is ￥26,710
￥39,376 total
includes taxes & fees
Aug 24 - Aug 25
Spacious Room with Rooftop Lounge & Scenic Views of Chicago
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
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 ￥61,242
￥89,025 total
includes taxes & fees
Aug 24 - Aug 25
2 Luxury Queen with Rooftop Lounge & City Views Near Attractions
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)
"Very convenient to the EL and the zoo. Large clean space. Perfect for a family trip"
Luxury SOHO Styled Two-Level Townhouse - Old Town
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
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!
50th Floor Mag Mile Studio VIEW, Pool, Gym, Balcony
Relax by the rooftop pool with a stunning city view, surrounded by lounge chairs and lush greenery.

50th Floor Mag Mile Studio VIEW, Pool, Gym, Balcony

10.0 out of 10, Exceptional, (7)
"Great stay in a fantastic location. Walk out the door to the metro station!"
50th Floor Mag Mile Studio VIEW, Pool, Gym, Balcony
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

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

10/10 Excellent
"Comfortable and accommodating when our flight was cancelled."
Norene 1-night trip
Posted 15 hours ago
Hotel Felix River North/Magnificent Mile