Holiday Homes in Chicago Station

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

Gilded Age Gold Coast Mansion with Parking, Deck, Fireplaces

Gilded Age Gold Coast Mansion with Parking, Deck, Fireplaces
Downtown Chicago
9.6 out of 10, Exceptional, (7 reviews)
"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

Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars
Near North Side
9.4 out of 10, Exceptional, (107 reviews)
"Great house and great location. The host was very attentive and helpful. "
United States
Jason S.
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars

Private, Discreet, Luxury Chicago Gold Coast Mansion, Event-Capable.

Private, Discreet, Luxury Chicago Gold Coast Mansion, Event-Capable.
Downtown Chicago
10.0 out of 10, Exceptional, (28 reviews)
"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.
Private, Discreet, Luxury Chicago Gold Coast Mansion, Event-Capable.

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

Beautiful Modern Designer Home ~ Downtown - 4-Bed/4-Bath
West Town
10.0 out of 10, Exceptional, (94 reviews)
"Perfect for a girls trip!!"
United States
Jessica B.
Beautiful Modern Designer Home ~ Downtown - 4-Bed/4-Bath

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

Luxurious Cozy 4BR 4-Story Gold Coast Villa with Free Parking
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"Very well kept.. Amazing location.."
United States
Michael J.
Luxurious Cozy 4BR 4-Story Gold Coast Villa with Free Parking

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

Old Town 3bd 3ba Coach House, Garage Parking Incl by AllSet Turnover
Near North Side
9.4 out of 10, Exceptional, (19 reviews)
"The neighborhood was fabulous. Varied and wonderful restaurants and bars. Near the Red line and Brown line L-stops, and an easy walk to Lincoln Park and the lake. Walking distance of a grocery. A wonderful location to seeing much of Chicago."
United States
Anonymous traveller
Old Town 3bd 3ba Coach House, Garage Parking Incl by AllSet Turnover

Historic luxury townhouse on Chicago's Gold Coast

Historic luxury townhouse on Chicago's Gold Coast
Downtown Chicago
9.4 out of 10, Exceptional, (80 reviews)
"Great property, great location!"
United States
Deb G.
Historic luxury townhouse on Chicago's Gold Coast

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, (104 reviews)
"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

Luxury House in the heart of Old Town with Parking
Near North Side
10.0 out of 10, Exceptional, (56 reviews)
"Great house, great location, great amenities!"
United States
Tracey R.
Luxury House in the heart of Old Town with Parking

Insta Worthy ^Prime Spot ^Patio ^Parking ^Fireplace

Insta Worthy ^Prime Spot ^Patio ^Parking ^Fireplace
Near North Side
9.2 out of 10, Wonderful, (63 reviews)
"Excellent place in great location. Good for large groups. "
United States
Patrick M.
Insta Worthy ^Prime Spot ^Patio ^Parking ^Fireplace

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

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, (63 reviews)
"We had a very nice experience and everyone was comfortable."
United States
Kirk D.
Spacious 4-Level/4-Bedroom Townhouse in West Loop

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

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

Luxury SOHO Styled Two-Level Townhouse - Old Town
Near North Side
10.0 out of 10, Exceptional, (18 reviews)
"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)

GROUP LUX in Old Town 4bd/3ba (+Rooftop/Parking)
Near North Side
9.8 out of 10, Exceptional, (26 reviews)
"The home was clean and just as advertised. We had a lovely stay."
United States
Emily W.
GROUP LUX in Old Town 4bd/3ba (+Rooftop/Parking)

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, (4 reviews)
"This place was great! Honestly can’t say enough good things about this place, it was super clean and spacious and had great kitchen. Had everything we could have asked for! The host was super informative and responsive even when I missed the entrance code. She also left a sweet note and some treat for our pup. "
United States
Angelique M.
Ideal Group Getaway: Prime Location, Parking, Backyard, Sunroom & Pet-Friendly

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

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

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

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

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

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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.

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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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