Holiday Homes in Central Chicago

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Check prices for these dates

In two weeks
3 Oct - 5 Oct
In one month
17 Oct - 19 Oct
In two months
14 Nov - 16 Nov
In three months
12 Dec - 14 Dec

Featured Holiday Homes in Central Chicago and around

Our top choices for Central Chicago holiday homes

Historic luxury townhouse on Chicago's Gold Coast
Fridge, microwave, oven, stovetop

Historic luxury townhouse on Chicago's Gold Coast

9.4 out of 10, Exceptional, (74)
"Large houseClean and well furnishedMix-up on checkin but manager on site fixed quickly.I highly recommend and would stay here again"
Historic luxury townhouse on Chicago's Gold Coast
Chicago Gold Coast Luxury Home Best Location walking distance to anywhere!
Terrace/patio

Chicago Gold Coast Luxury Home Best Location walking distance to anywhere!

10.0 out of 10, Exceptional, (23)
"I cannot express how wonderful the stay was! From the communication level of the hosts to the details and cleanliness let alone the beauty of this home, it was absolutely wonderful in every way! We will absolutely be staying here again for any future needs!"
Chicago Gold Coast Luxury Home Best Location walking distance to anywhere!
Spacious 2BR Unit Skyline View - Walk to McCormick
Exterior

Spacious 2BR Unit Skyline View - Walk to McCormick

8.0 out of 10, Very good, (1)
"Front desk was kind and helpful. Private parking and gate was a nice touch. Only 1 working elevator was unfortunate with the large group I was with. And halls were very humid but the rooms were nice. Comfy beds, clean stay! Shared balcony was fun to hangout at too."
Spacious 2BR Unit Skyline View - Walk to McCormick
Elegant 4 br Old Town Home; Private Yard; Parking; Amazing Location
Full-sized fridge, microwave, oven, stovetop

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

9.8 out of 10, Exceptional, (100)
"Loved being able to walk to Second City, Jeni’s, and grocery store. "
Elegant 4 br Old Town Home; Private Yard; Parking; Amazing Location
Insta Worthy ^Prime Spot ^Patio ^Parking ^Fireplace
Fridge, microwave, oven, stovetop

Insta Worthy ^Prime Spot ^Patio ^Parking ^Fireplace

9.2 out of 10, Wonderful, (58)
"Plenty of space for our large group, great location and timely communication from host. We were able to walk to nearby restaurants and bars. Would stay again. "
Insta Worthy ^Prime Spot ^Patio ^Parking ^Fireplace
Old Town 3bd 3ba Coach House, Garage Parking Incl by AllSet Turnover
Fridge, microwave, oven, dishwasher

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
Fridge, microwave, oven, stovetop

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
Family-Friendly South Loop Escape by RedAwning
Fridge, microwave, oven, dishwasher

Family-Friendly South Loop Escape by RedAwning

Family-Friendly South Loop Escape by RedAwning
Luxury House in the heart of Old Town with Parking
Interior

Luxury House in the heart of Old Town with Parking

10.0 out of 10, Exceptional, (52)
"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
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars
Interior

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

9.4 out of 10, Exceptional, (99)
"Good for our get together."
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars
Luxury SOHO Styled Two-Level Townhouse - Old Town
Terrace/patio

Luxury SOHO Styled Two-Level Townhouse - Old Town

10.0 out of 10, Exceptional, (16)
"Great location in Old Town! Easy walking to the beach and many restaurants. Ample space and clean property."
Luxury SOHO Styled Two-Level Townhouse - Old Town
Spacious 2BR Group Stay near McCormick & Wintrust
Interior

Spacious 2BR Group Stay near McCormick & Wintrust

10.0 out of 10, Exceptional, (1)
"Very clean, visually appealing space with plenty of room for our group. Check in and parking were straightforward and front desk staff were very helpful, though occasionally there won't be anyone at the front desk, making things a little confusing. Towels, toothbrushes, and little toothpastes were nearly stacked on the beds when we arrived which was a nice touch. Property is close to the train station as well as plenty of restaurants. Host was very responsive as well. Would recommend!"
Spacious 2BR Group Stay near McCormick & Wintrust
GROUP LUX in Old Town 4bd/3ba (+Rooftop/Parking)
Fridge, microwave, oven, stovetop

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

9.8 out of 10, Exceptional, (23)
"Loved everything. A great place to gather family."
GROUP LUX in Old Town 4bd/3ba (+Rooftop/Parking)
McCormick 3B/2Ba Corner Oasis for up to 10 guests
Interior

McCormick 3B/2Ba Corner Oasis for up to 10 guests

McCormick 3B/2Ba Corner Oasis for up to 10 guests
Ideal Group Getaway: Prime Location, Parking, Backyard, Sunroom & Pet-Friendly
Interior

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
Spectacular Gold Coast Villa Near Beach w/ Parking
Terrace/patio

Spectacular Gold Coast Villa Near Beach w/ Parking

10.0 out of 10, Exceptional, (1)
"Great house for our family vacation to Chicago!"
Spectacular Gold Coast Villa Near Beach w/ Parking
The Chicago Hotel Collection River North
Dining

The Chicago Hotel Collection River North

The Chicago Hotel Collection River North
The Hide-Away | South Loop Apartment
Exterior detail

The Hide-Away | South Loop Apartment

The Hide-Away | South Loop Apartment
Secret Gallery on the Park - 2bd/1ba + 1bd/1ba
Fridge, microwave, oven, stovetop

Secret Gallery on the Park - 2bd/1ba + 1bd/1ba

Secret Gallery on the Park - 2bd/1ba + 1bd/1ba
City Studio Escape Bright, Sleek & Modern
Outdoor dining

City Studio Escape Bright, Sleek & Modern

City Studio Escape Bright, Sleek & Modern
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

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

10/10 Excellent
"This is a beautiful hotel and so conveniently located - easy to walk to museums and the Mag Mile"
amy 1-night trip
Posted 1 day ago
Palmer House a Hilton Hotel

Find out more about Central Chicago

Find out more about Central Chicago

Central Chicago Holiday Homes information

Number of reviews
310
Accommodation
87 Holiday Homes
Lowest Price
Highest Price

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