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Browse Select Central Chicago Vacation Homes

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

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

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

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

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

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!

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

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

Family-Friendly South Loop Escape by RedAwning

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

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

The price is CA $750
CA $1,013 total
includes taxes & fees
Sep 2 - Sep 3
2 Connecting Suites at a 4⭐️ Hotel

Spacious Room with Rooftop Lounge & Scenic Views of Chicago

The price is CA $249
CA $368 total
includes taxes & fees
Aug 24 - Aug 25
Spacious Room with Rooftop Lounge & Scenic Views of Chicago

Cozy Private Room in Prime Downtown Chicago

Cozy Private Room in Prime Downtown Chicago

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

The price is CA $572
CA $831 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

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

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

Clean & Modern • Central Location • Free Coffee!

Clean & Modern • Central Location • Free Coffee!

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