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Vacation Homes in Chicago Station

Amazing 3-bedroom house with WiFi and AC in awesome Chicago

Amazing 3-bedroom house with WiFi and AC in awesome Chicago

Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!

Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!

Chic and Spacious Bi-level 3BD in Bucktown!

2.0 star property
9.8 out of 10, Exceptional, (8)
"Property was comfortable, clean, and in a great location."
Chic and Spacious Bi-level 3BD in Bucktown!

Spacious Newly Renovated Home in Lincoln Park w/ Outdoor Living & Dining Area!

10.0 out of 10, Exceptional, (4)
"We had a fantastic stay! The property was perfect for kids — safe, clean, and had plenty of space to play. The outdoor space is perfect for morning coffee, lounging, afternoon cocktails, and dinner under the stars. This location was unbeatable, close to everything we wanted to do. Couldn’t have asked for a better spot for a family getaway in the city. Highly recommend!"
Spacious Newly Renovated Home in Lincoln Park w/ Outdoor Living & Dining Area!

Spacious 5-bedroom house great for large groups

10.0 out of 10, Exceptional, (1)
Spacious 5-bedroom house great for large groups

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

9.2 out of 10, Wonderful, (17)
"Very quiet and close to CTA , Old Town easy access to the city"
Old Town 3bd 3ba Coach House, Garage Parking Incl by AllSet Turnover

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

10.0 out of 10, Exceptional, (90)
"Awesome location, plenty of space, timely communication, clean. We loved it!"
Beautiful Modern Designer Home ~ Downtown - 4-Bed/4-Bath

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

10.0 out of 10, Exceptional, (2)
"My new go to spot to stay in Chicago. Really loved the space and location, easy to get around. "
Rest Easy in the East Village - Quiet Street Only Steps to Top Restaurants, Bars, and Public Transportation by AllSet Turnover

Beautiful duplex in the heart of bucktown.

10.0 out of 10, Exceptional, (3)
"Great location and host was very responsive."
Beautiful duplex in the heart of bucktown.

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

9.4 out of 10, Exceptional, (22)
"Beautifully maintained property in residential neighborhood proximate to fantastic food and beverage / public transportation and quick cab ride from all major Chicago attractions. "
EAST VILLAGE 4-LEVEL-HOUSE WITH 5 BATHS & COVERED ATTACHED GARAGE

Spacious / New Home - 8BD/4BTH - Sleeps 16 + Garage!

8.0 out of 10, Very Good, (7)
"The space - number of rooms and bathrooms - was great for a big group. We were able to sleep multiple families comfortably with no issues getting ready with the number of bathrooms. There was plenty of free street parking close, so we also didn't have any problems finding parking for all our cars. Some more specific instructions on how to use the key pad (to enter and lock) would be helpful, but otherwise no complaints! I would recommend this Vrbo! "
Spacious / New Home - 8BD/4BTH - Sleeps 16 + Garage!

Wicker Park Entire House, Private Yard and Parking!

10.0 out of 10, Exceptional, (13)
"We came into town for some weekend parties. It was a great location and we were all comfortable. Nice place"
Wicker Park Entire House, Private Yard and Parking!

Private Historic Coach House Wicker Park

10.0 out of 10, Exceptional, (64)
"This place was a perfect rental for a girls trip to Chicago. Great location, walkable to so many amazing shops bars, and restaurants. All of us slept amazing with very comfortable beds, pillows, and quality sheets. We also really appreciated all the extra tiny amenities like a blow dryer, make up mirror, and of course, a wine opener. Thank you so much for the Incredibles stay "
Private Historic Coach House Wicker Park

Lincoln Park Cozy 3bd Home near Zoo | Lake | Shops

9.8 out of 10, Exceptional, (36)
"Great location. Great place to stay. "
Lincoln Park Cozy 3bd Home near Zoo | Lake | Shops

Fantastic Home in Wicker Park

10.0 out of 10, Exceptional, (12)
"Beautiful house in a lively neighborhood, had a great time."
Fantastic Home in Wicker Park

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

2.0 star property
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."
Cozy 1-bedroom house in charming Chicago with WiFi, AC, Washer/Dryer

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

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

Brand New 4BR in Heart of Chicago

Brand New 4BR in Heart of Chicago

Remodeled 1890 Chicago Greystone, 4bd 3.5ba & Gym

10.0 out of 10, Exceptional, (6)
"Upscale tri level home, easy location to get to and Uber from. House is very well designed and set up for a larger family group. 4 nice bedrooms with really nice bathrooms and a small workout area. Living room and kitchen open up to a back deck area with lower level sitting spaces. Great place to stay for concerts or just an easy location to visit the pier or soldier field or Wrigley or white Sox. We enjoyed our week. "
Remodeled 1890 Chicago Greystone, 4bd 3.5ba & Gym

Spacious 5 BR / King Size Beds + Private Parking!

9.6 out of 10, Exceptional, (13)
"The place was wondeful and the host was very easy to communicate with and prompt in his responses. 10/10 would stay here again!"
Spacious 5 BR / King Size Beds + Private Parking!
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

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 2025 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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