Holiday Homes in Chicago Station

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Featured Holiday Homes in Chicago Station

Gilded Age Gold Coast Mansion with Parking, Deck, Fireplaces

Downtown Chicago
10.0 out of 10, Exceptional, (6)
"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! "
United States
Raleigh H.
Gilded Age Gold Coast Mansion with Parking, Deck, Fireplaces

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

Near North Side
9.4 out of 10, Exceptional, (105)
"Awesome space for our large group! Location couldn’t have been better - on a very nice street with tons of bars and restaurants near by."
United States
Elias P.
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars

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

Downtown Chicago
10.0 out of 10, Exceptional, (24)
"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!"
United States
Erica S.
Chicago Gold Coast Luxury Home Best Location walking distance to anywhere!

Beautiful Modern Designer Home ~ Downtown - 4-Bed/4-Bath

West Town
10.0 out of 10, Exceptional, (92)
"Awesome location, plenty of space, timely communication, clean. We loved it!"
United States
Julia D.
Beautiful Modern Designer Home ~ Downtown - 4-Bed/4-Bath

Luxurious Cozy 4BR 4-Story Gold Coast Villa with Free Parking

Downtown Chicago
Luxurious Cozy 4BR 4-Story Gold Coast Villa with Free Parking

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

Near North Side
9.4 out of 10, Exceptional, (19)
"Overall, our stay was great! Checking in and out was easy and speedy, and the location is fantastic for those who like to spend time downtown (the property is within walking distance of the Brown and Red lines). A garage space was greatly appreciated for those who would drive, but traveling to/from O’Hare on the L was easy. We (6 adults) enjoyed our time and the neighborhood."
United States
Jordan R.
Old Town 3bd 3ba Coach House, Garage Parking Incl by AllSet Turnover

Historic luxury townhouse on Chicago's Gold Coast

Downtown Chicago
9.4 out of 10, Exceptional, (79)
"Terrific location and fabulous building!"
Canada
Janna T.
Historic luxury townhouse on Chicago's Gold Coast

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

Near North Side
9.8 out of 10, Exceptional, (103)
"Very nicely kept property in a good location. Beds were comfortable and kitchen and baths were very clean and nicely stocked with essentials (towels, soap etc) "
United States
Alan A.
Elegant 4 br Old Town Home; Private Yard; Parking; Amazing Location

Luxury House in the heart of Old Town with Parking

Near North Side
10.0 out of 10, Exceptional, (54)
"Really great house in very cool neighborhood. There were a few tech issues we had and the owner was very responsive. Great place for big family gathering. Short walk to Lake Michigan. "
United States
Jay G.
Luxury House in the heart of Old Town with Parking

Insta Worthy ^Prime Spot ^Patio ^Parking ^Fireplace

Near North Side
9.2 out of 10, Wonderful, (61)
"My group and I genuinely enjoyed staying at this property! It was easy to check in and was also in a great location!"
United States
Erin H.
Insta Worthy ^Prime Spot ^Patio ^Parking ^Fireplace

Last-Minute Chicago home with Rooftop Views +Private HOT TUB -Garage-Sleeps 12

West Town
10.0 out of 10, Exceptional, (2)
"Stayed in Chicago for a trade show. Great location and well kept property "
United States
Aaron E.
Last-Minute Chicago home with Rooftop Views +Private HOT TUB -Garage-Sleeps 12

Spacious 4-Level/4-Bedroom Townhouse in West Loop

West Town
10.0 out of 10, Exceptional, (61)
"We really loved staying at this property. I would definitely book this again. Very clean and comfortable."
United States
mary s.
Spacious 4-Level/4-Bedroom Townhouse in West Loop

NEW! Spacious 3-Bed West Loop Townhouse, 1 Car Garage

Downtown Chicago
NEW! Spacious 3-Bed West Loop Townhouse, 1 Car Garage

Luxury SOHO Styled Two-Level Townhouse - Old Town

Near North Side
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."
United States
John Z.
Luxury SOHO Styled Two-Level Townhouse - Old Town

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

Near North Side
9.8 out of 10, Exceptional, (26)
"Loved everything. A great place to gather family."
United States
DENISE G.
GROUP LUX in Old Town 4bd/3ba (+Rooftop/Parking)

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

Near North Side
10.0 out of 10, Exceptional, (3)
"We enjoyed our stay great host "
United States
Janeth G.
Ideal Group Getaway: Prime Location, Parking, Backyard, Sunroom & Pet-Friendly

Steps to Fulton Market Downtown 4 bedroom Entire Home Sleeps 11 with City Views

West Town
10.0 out of 10, Exceptional, (3)
"Clean, spacious, and well equipped for renters. Our group enjoyed this home immensely and its easy walk to all Fulton Market attractions. Owner is thoughtful and very responsive. I hope to stay again next time I'm in the area!"
United States
C D.
Steps to Fulton Market Downtown 4 bedroom Entire Home Sleeps 11 with City Views

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

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

Stylish 3BR Townhouse with 2 Jacuzzi and 1 private garage spot

2.0 star property
Downtown Chicago
Stylish 3BR Townhouse with 2 Jacuzzi and 1 private garage spot

Centrally Located Chicago Townhome

Armour Square
Centrally Located Chicago Townhome
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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Booking Chicago Station Holiday Homes

What types of Holiday Homes can I find in Chicago Station?

Holiday Homes in Chicago Station are available for a range of different budgets and trip preferences, whether you’re an occasional traveller for leisure or a regular traveller for business, booking for a shorter or longer stay. Browse a wide selection of available options on Expedia.

How much does Holiday Homes cost in Chicago Station?

Prices for Chicago Station Holiday Homes start from * and vary throughout the year. Expedia can help you find great deals on cheap Holiday Homes in Chicago Station.

How to find the best deals on Chicago Station Holiday Homes?

Use Expedia’s range of useful search filters to help find cheap Holiday Homes in Chicago Station that suits you. Filter by price and guest rating to find some of the best and most popular Holiday Homes available in Chicago Station at an affordable price.

Why should I choose Expedia to book a Chicago Station Holiday Homes ?

Expedia has a wide selection of Chicago Station Holiday Homes to choose from at some of the best prices available. Book with Expedia for great deals on Chicago Station Holiday Homes and an excellent customer service experience handling your booking.

What is the cancellation policy on booking Chicago Station Holiday Homes?

Each Chicago Station Holiday Homes has its own cancellation policy. Please see the specific Holiday Homes for details. Flexibility is important. That’s why many Chicago Station Holiday Homes available on Expedia offer free cancellation. Look out for options marked “Free cancellation”.

*Prices and availability are subject to change. Additional terms may apply. 

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