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Vacation Homes in Chicago Station

NEW to the market! Relax with family in a super Lux Custom SFH. West town.

2.0 star property
West Town
NEW to the market! Relax with family in a super Lux Custom SFH. West town.

Chic and Spacious Bi-level 3BD in Bucktown!

2.0 star property
Bucktown
9.8 out of 10, Exceptional, (15)
"Location is good. Close to the city, but not too close. Good access to CTA. Check in was straightforward and host promptly responsive to a minor issue with WIFI. Would stay here again. "
United States
Tim R.
Chic and Spacious Bi-level 3BD in Bucktown!

Spacious 5-bedroom house great for large groups

West Town
10.0 out of 10, Exceptional, (2)
"The property was lovely and there was plenty of space to sleep, even for a large group. I would absolutely stay here again."
United States
John M.
Spacious 5-bedroom house great for large groups

Bee's Knees - Ritzy, 1924 Hollywoodesque Bungalow

Humboldt Park
10.0 out of 10, Exceptional, (16)
"Good"
United States
William C.
Bee's Knees - Ritzy, 1924 Hollywoodesque Bungalow

Wicker Park Entire House, Private Yard and Parking

West Town
10.0 out of 10, Exceptional, (15)
"Excellent home in a great location. We loved it. "
United States
David F.
Wicker Park Entire House, Private Yard and Parking

The Bucktown House - Heart of Bucktown/Wicker Park, 10 Min Uber to Downtown

Bucktown
9.8 out of 10, Exceptional, (33)
"Great location to get to all the things we wanted to do. The house is perfect!"
United States
Anonymous traveler
The Bucktown House - Heart of Bucktown/Wicker Park, 10 Min Uber to Downtown

Beautiful duplex in the heart of bucktown.

Bucktown
10.0 out of 10, Exceptional, (5)
"Great location and host was very responsive."
United States
Morgan F.
Beautiful duplex in the heart of bucktown.

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

Heart of Chicago 5 Bedroom Modern 12 guest West Bucktown Home

West Town
6.0 out of 10, (5)
"We stayed at this property for the holiday weekend and the experience was very disappointing. The home was not as advertised and was in poor condition, making the stay uncomfortable and even unsafe.When we arrived, there was a large hole in the bathroom wall with drywall debris all over the floor, which was an immediate red flag. Cleaning supplies were scattered throughout the house, and the overall cleanliness was lacking—floors, counters, and even the coffee maker had to be cleaned before...
United States
Happygail
Heart of Chicago 5 Bedroom Modern 12 guest West Bucktown Home

EAST VILLAGE 4-LEVEL-HOUSE WITH 5 BATHS & COVERED ATTACHED GARAGE

West Town
9.0 out of 10, Wonderful, (24)
"The property was great and accommodated 11 people nicely "
United States
Marni S.
EAST VILLAGE 4-LEVEL-HOUSE WITH 5 BATHS & COVERED ATTACHED GARAGE

Wicker Park 6bd/4ba, Steps from CTA, Parking Incl by AllSet Turnover

West Town
9.0 out of 10, Wonderful, (6)
"Very convenient to the Metra blue line, lots of bars and restaurants in the neighborhood. "
United States
John D.
Wicker Park 6bd/4ba, Steps from CTA, 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)
"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

Private Historic Coach House Wicker Park

West Town
10.0 out of 10, Exceptional, (66)
"The property was charming, clean, and it contained anything you would need for your stay. The neighborhood was lovely with wonderful restaurants. We truly enjoyed our stay."
United States
Denise E.
Private Historic Coach House Wicker Park

Vital Urban: Spa Inspired Retreat

West Town
9.8 out of 10, Exceptional, (8)
"Wonderful stay! The property was clean, super comfortable and very well equipped with everything we needed! The location was perfect! The host was very responsive and all information/ instructions about the property were easy to understand. We will definitely stay again next time we’re in Chicago! "
United States
Jeanne A.
Vital Urban: Spa Inspired Retreat

LUXURIOUS LINCOLN PARK Home w/ Rooftop +parking

Lincoln Park
9.6 out of 10, Exceptional, (15)
"Fantastic stay. Comfy beds, great location, clean and plenty of space. Tons of walkable restaurants and shops. We had so much fun and would definitely return. It is close to the L, however the sound machines drowned out any noise. We slept so good!! "
United States
Shannon B.
LUXURIOUS LINCOLN PARK Home w/ Rooftop +parking

Spacious Townhome! 3 bedrooms & 2 complete bath and 2 outdoor Patios, Near Train

Lincoln Park
10.0 out of 10, Exceptional, (16)
"We had a great stay here. Really added to our enjoyment of Chicago. Marco is a great host. The place is very comfortable."
United States
Julie S.
Spacious Townhome! 3 bedrooms & 2 complete bath and 2 outdoor Patios, Near Train

Cozy 1-bedroom house in charming Chicago with WiFi, AC, Washer/Dryer

2.0 star property
West Town
9.8 out of 10, Exceptional, (6)
"This is indeed a cozy 1-bedroom house. It has been remodeled and is very attractive and comfortable. We will stay here again when we visit family in the Wicker Park area."
United States
Walter E.
Cozy 1-bedroom house in charming Chicago with WiFi, AC, Washer/Dryer

Rest Easy in the East Village - Quiet Street Only Steps to Top Restaurants, Bars, and Public Transportation by AllSet Turnover

West Town
10.0 out of 10, Exceptional, (3)
"My new go to spot to stay in Chicago. Really loved the space and location, easy to get around. "
United States
demi c.
Rest Easy in the East Village - Quiet Street Only Steps to Top Restaurants, Bars, and Public Transportation by AllSet Turnover

Cozy Studio Suite, Steps from River North & Shops

Near North Side
8.0 out of 10, Very Good, (1)
"I live in the far west suburbs and occasionally need to visit the city for work a couple days in a row which prompts me to stay the night. This property was absolutely perfect, safe, and clean. The price was appropriate. My only 2 suggestions would be to have a hairdryer and include parking. Those are the two things that dropped my score. The location was fantastic as it sits near shopping, Whole Foods, and restaurants but in a quiet neighborhood. I plan on staying again!"
United States
Bridgett K.
Cozy Studio Suite, Steps from River North & Shops

Remodeled 1890 Chicago Greystone, 4bd 3.5ba & Gym

Near West Side
10.0 out of 10, Exceptional, (8)
"Great Location, beautiful home and Aaron was very helpful"
United States
Pamela A.
Remodeled 1890 Chicago Greystone, 4bd 3.5ba & Gym
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

Find out more about Chicago Station

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

At Expedia, you’ll find great Chicago Station Vacation Homes for your family vacation, business trip, romantic weekend break, and more. If you’re planning a vacation with kids, try using the traveler experience filter to select “Family-friendly” Chicago Station Vacation Homes. Or, if you’re traveling for work, you can check the “Business-friendly” box to find business-oriented places to stay in Chicago Station. While you’re making your decision, you can use our map facility to view your shortlisted properties and their distance from Chicago Station, or nearby places of interest. There are great places to stay for every budget, so if you need cheap Vacation Homes in Chicago Station, use our simple search function to help you secure a great deal.

How much do Vacation Homes cost in Chicago Station?

The price per night for Chicago Station Vacation Homes in 2026 can start from as low as *. The cost of Vacation Homes varies depending on a number of factors: the dates of your stay, the exact location of the accommodation, and whether there are any special events taking place near Chicago Station, to name just three. When there’s a high demand for rooms in Chicago Station, this can cause prices to increase, whereas traveling during a quieter time of the year can mean lower prices. Booking through Expedia can help you find some of the best deals for cheap Vacation Homes in Chicago Station, so you can sleep easy without going over your budget.

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

Expedia’s search function can help you find some of the best deals on Chicago Station Vacation Homes. You can select a minimum and maximum price per night according to your budget, and filter by guest ratings and star ratings to ensure you find the right Vacation Homes for your needs. Changing the sort order according to price can also help you to view cheap Vacation Homes in Chicago Station at a glance, and you can combine this with our own picks to highlight some of the best available offers. Don’t forget, if you’re an Expedia Rewards member, you can use the “Member Prices” filter to make extra savings on your booking.

Why should I choose Expedia to book Chicago Station Vacation Homes?

Booking with Expedia allows you to browse a wide selection of places to stay in Chicago Station, complete with search filters that make it easy to locate Vacation Homes that best meet your specific requirements. Our clear and easy-to-use search function makes it effortless to compare amenities, prices, property types, neighborhoods, and much more. At Expedia, you can also find flights, car rental, and activities, and you can combine your bookings for greater savings. Plus, Expedia Rewards members accrue points on all eligible purchases. Build your points total to gain discounts on subsequent bookings in the future. Membership is free, so go ahead and join.

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

At Expedia, we understand that plans change, and the good news is you can cancel many bookings for Chicago Station Vacation Homes with a full refund, depending on the rules and restrictions. For example, some Vacation Homes may not give refunds if you cancel your booking within 24 or 48 hours of your arrival date, and some bookings are non-refundable. Be sure to view the policies provided by the Chicago Station Vacation Homes, and confirm the exact cancellation window on your selected location’s details page. If free cancellation is important to you, you can filter for the “Fully refundable” payment type when you search for your Vacation Homes.

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

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