Holiday Homes in Chicago Station

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Check prices for these dates

In two weeks
1 May - 3 May
In two months
12 June - 14 June
In three months
10 July - 12 July
In four months
7 Aug - 9 Aug

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

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, (67 reviews)
"This worked perfectly for us. The beds were nice and comfy. One of the rooms was naturally cooler than the others, which was perfect for a family member who preferred that. We could hear the train but it was a soft sound that I found rather soothing."
United States
Elise N.
Heart of the City Group Hub • Patio • Fireplace • Parking
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, (81 reviews)
"Great location and really nice home "
United States
Matthew H.
Historic luxury townhouse on Chicago's Gold Coast
Interior

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

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

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, (9 reviews)
"Beautiful property. Great location. Very accommodating host!"
United States
Nancy C.
Gilded Age Gold Coast Mansion with Parking, Deck, Fireplaces
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, (108 reviews)
"Great location in Old Town. We loved walking to restaurants, cafes, and church! The house was great for our group. "
United States
Paul R.
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars
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, (56 reviews)
"Our host was very responsive and generous. Beautiful home in a beautiful neighborhood."
United States
Laura A.
Luxury House in the heart of Old Town with Parking
Beach nearby

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, (32 reviews)
"host was very welcoming, and very response to any questions we had."
United States
Tad W.
Private, Discreet, Luxury Chicago Gold Coast Mansion, Event-Capable.
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, (105 reviews)
"Perfect place for a large group and easily walkable to local attractions! Inna was so helpful and responsive throughout our stay!"
United States
Juliana C.
Elegant 4 br Old Town Home; Private Yard; Parking; Amazing Location
Microwave, oven, stovetop, dishwasher

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

Stylish 3BR Townhouse with 2 Jacuzzi and 1 private garage spot
Downtown Chicago
Stylish 3BR Townhouse with 2 Jacuzzi and 1 private garage spot
Smart TV, fireplace

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, (96 reviews)
"Good stay. All worked well. Accommodated 8 adults comfortably without issue. Host was very responsive to questions about detailed needs booking. Also very responsive to resolving a few very minor items during our stay. "
United Kingdom
Graham W.
Beautiful Modern Designer Home ~ Downtown - 4-Bed/4-Bath
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
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, (19 reviews)
"Great stay in a great location! "
United States
Greg W.
Luxury SOHO Styled Two-Level Townhouse - Old Town
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, (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
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, (27 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)
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, (5 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
Smart TV, video game console, DVD player, books

Bright, Cozy Apartment by Downtown & Train Stop; Great for Couples/Small Groups

Bright, Cozy Apartment by Downtown & Train Stop; Great for Couples/Small Groups
Chicago
8.0 out of 10, Very good, (2 reviews)
"To preface my review, I think this place definitely has the **potential** to be a 5 star stay. The location is phenomenal and the apartment as a whole is very nice. I really liked the TV in the bedroom since it was great to watch movies on it. However, this stay earns only 3 stars for the following reasons. First, when I arrived, Kam did not provide any directions on how to get into my apartment or where the apartment would be located within his building, even though I messaged him on VRBO a...
United States
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Bright, Cozy Apartment by Downtown & Train Stop; Great for Couples/Small Groups
Exterior detail

The Hide-Away | South Loop Apartment

The Hide-Away | South Loop Apartment
Near South Side
The Hide-Away | South Loop Apartment
2 bedrooms

The Chicago Hotel Collection River North

The Chicago Hotel Collection River North
Downtown Chicago
The Chicago Hotel Collection River North
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

2/10 Terrible
"Stay away from this place. Old, dirty, dilapidated hallways, unsafe, marijuana odor, dingy and completely dark elevators. Filled with people under the influence (walk-ins that were coming and going to the bar we assumed) dressed inappropriately. We arrived on a Friday night and left first thing the next morning. Will never trust the ratings from hotels.com again. "
Ken 1-night trip
Posted 5 hours ago
The Chicago Hotel Collection Ambassador Gold Coast

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

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