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Holiday Homes in Chicago Station

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Check prices for these dates

In two weeks
31 July - 2 Aug
In two months
11 Sept - 13 Sept
In three months
9 Oct - 11 Oct
In four months
6 Nov - 8 Nov

Our top choices for Chicago Station (Brown Line) holiday homes

Exterior detail

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

Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars
Near North Side
9.4 out of 10, Exceptional, (118 reviews)
"Parking is very secure"
United States
James
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars
Exterior detail

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

Elegant 4 br Old Town Home; Private Yard; Parking; Amazing Location
Near North Side
9.8 out of 10, Exceptional, (113 reviews)
"Host was welcoming and easily available for communication. "
United States
Kate G.
Elegant 4 br Old Town Home; Private Yard; Parking; Amazing Location
Beach

Gilded Age Gold Coast Mansion with Parking, Deck, Fireplaces

Gilded Age Gold Coast Mansion with Parking, Deck, Fireplaces
Downtown Chicago
9.8 out of 10, Exceptional, (13 reviews)
"Easy check in, property was clean and had tons of space. Communication was speedy and everyone loved the soft comforters on the beds. I would recommend anyone to stay here. "
United States
Cole M.
Gilded Age Gold Coast Mansion with Parking, Deck, Fireplaces
Exterior detail

Heart of the City Group Hub • Patio • Fireplace • Parking

Heart of the City Group Hub • Patio • Fireplace • Parking
Near North Side
9.2 out of 10, Wonderful, (75 reviews)
"Very clean and easy to use. Near by accommodations as well."
United States
Richard S.
Heart of the City Group Hub • Patio • Fireplace • Parking
Interior

Private Historical Mansion,Luxury Home in Chicago’s Gold Coast, Event-Capable.

Private Historical Mansion,Luxury Home in Chicago’s Gold Coast, Event-Capable.
Downtown Chicago
10.0 out of 10, Exceptional, (34 reviews)
"Incredible place - pristine, perfect location, all kinds of room to spread out across 4 floors. Would absolutely stay there again "
United States
John B.
Private Historical Mansion,Luxury Home in Chicago’s Gold Coast, Event-Capable.
Exterior

Historic luxury townhouse on Chicago's Gold Coast

Historic luxury townhouse on Chicago's Gold Coast
Downtown Chicago
9.4 out of 10, Exceptional, (88 reviews)
"You can’t ask for a better location! We walked to downtown, Millenium Park, and Old Town. The property is gorgeous and a taste of old Chicago with beautiful woodwork and huge bedrooms. The six of us had our own space and were very comfortable."
United States
Angela
Historic luxury townhouse on Chicago's Gold Coast
Interior

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

GROUP LUX in Old Town 4bd/3ba (+Rooftop/Parking)
Near North Side
9.8 out of 10, Exceptional, (28 reviews)
"Great locationGood for families alsoParking is difficult but manageable "
United States
Carletta T.
GROUP LUX in Old Town 4bd/3ba (+Rooftop/Parking)
Exterior detail

Luxury SOHO Styled Two-Level Townhouse - Old Town

Luxury SOHO Styled Two-Level Townhouse - Old Town
Near North Side
10.0 out of 10, Exceptional, (21 reviews)
"Great stay in a great location! "
United States
Greg W.
Luxury SOHO Styled Two-Level Townhouse - Old Town
Interior

Luxury House in the heart of Old Town with Parking

Luxury House in the heart of Old Town with Parking
Near North Side
10.0 out of 10, Exceptional, (59 reviews)
"The house was in a great area, easily walkable to coffee shops and restaurants, and only a short car ride away from downtown. The host was very responsive and accommodating. "
United States
Jessica W.
Luxury House in the heart of Old Town with Parking
Outdoor dining

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

Last-Minute Chicago home with Rooftop Views +Private HOT TUB -Garage-Sleeps 12
West Town
10.0 out of 10, Exceptional, (3 reviews)
"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
Smart TV

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

Spacious 4-Level/4-Bedroom Townhouse in West Loop
West Town
10.0 out of 10, Exceptional, (64 reviews)
"We had a very nice experience and everyone was comfortable."
United States
Kirk D.
Spacious 4-Level/4-Bedroom Townhouse in West Loop
TV

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

NEW! Spacious 3-Bed West Loop Townhouse, 1 Car Garage by AllSet Turnover
Downtown Chicago
NEW! Spacious 3-Bed West Loop Townhouse, 1 Car Garage by AllSet Turnover
Exterior detail

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

Ideal Group Getaway: Prime Location, Parking, Backyard, Sunroom & Pet-Friendly
Near North Side
10.0 out of 10, Exceptional, (6 reviews)
"Great to have so much space for our family of four and a garage to park in. We were able to walk to eat in the heart of Old Town easily. The host was very accommodating with our last minute reservation!"
United States
Michelle H.
Ideal Group Getaway: Prime Location, Parking, Backyard, Sunroom & Pet-Friendly
Smart TV, fireplace

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

Steps to Fulton Market Downtown 4 bedroom Entire Home Sleeps 11 with City Views
West Town
10.0 out of 10, Exceptional, (3 reviews)
"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
Coffee/tea maker, fridge, microwave, oven

Centrally Located Chicago Townhome

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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Top Chicago Station Hotel Reviews

The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

10/10 Excellent
"They place was very nice"
Javaughn 1-night trip
Posted less than an hour ago
The Chicago Hotel Collection Ambassador Gold Coast

Find out more about Chicago Station

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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