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Vacation Homes in Chicago 27th Street Station

Spacious 2BR Group Stay near McCormick Place & Wintrust Arena

Near South Side
8.8 out of 10, Excellent, (3)
"Communication from host. Amenities. Work out center"
United States
Sue R.
Spacious 2BR Group Stay near McCormick Place & Wintrust Arena

Lux Home in Chicago 7mins Downtown

Bronzeville
9.8 out of 10, Exceptional, (28)
"Larry was super responsive, the property was spotless, the location perfect. Our group of friends loved it. We will be back! "
United States
Kyle B.
Lux Home in Chicago 7mins Downtown

Bronzeville Jazz Room. Beautiful, cozy, centered, relaxing, rustic.

2.0 star property
Bronzeville
10.0 out of 10, Exceptional, (1)
"The property was clean. The house was nice and neat. I enjoyed my stay. "
United States
Lamyha S.
Bronzeville Jazz Room. Beautiful, cozy, centered, relaxing, rustic.

1 #23 - 4 Bedroom Condo - McCormick Place, Wintrust Arena, Chinatown

Chinatown
9.8 out of 10, Exceptional, (10)
"Not one of these fancy, interior-design-focused places by any means, but the beds and pillows were very comfortable, great water pressure, high quality keurig and appliances, and an incredible incredible location. Highly recommended."
United States
Michelle T.
1 #23 - 4 Bedroom Condo - McCormick Place, Wintrust Arena, Chinatown

Family-Friendly South Loop Escape by RedAwning

Near South Side
Family-Friendly South Loop Escape by RedAwning

Mayors Manor, Zen Garden Oasis, Hot Tub & Sauna in Central Chicago, 8-12 guests

Bridgeport
9.4 out of 10, Exceptional, (21)
"The owners were SUPER helpful and their communication was SUPERB!"
United States
Juan B.
Mayors Manor, Zen Garden Oasis, Hot Tub & Sauna in Central Chicago, 8-12 guests

Lakefront property , minutes from McCormick Place and Downtown Chicago.

Bronzeville
9.8 out of 10, Exceptional, (8)
"Overall great stay, great host"
United States
Tyrese M.
Lakefront property , minutes from McCormick Place and Downtown Chicago.

Renovated 6 Bedroom 5 Bathroom Home 10 Minutes from Downtown Chicago

Bronzeville
9.2 out of 10, Wonderful, (20)
"The house was beautiful and check-in was easy. It was a great place for my family to gather and spend time together. There was plenty of room for everyone and the kitchen was a delight to work in. "
United States
Linda P.
Renovated 6 Bedroom 5 Bathroom Home 10 Minutes from Downtown Chicago

Hamaline Luxury - Guest House

Bronzeville
9.4 out of 10, Exceptional, (3)
"Good stay close to a lot of bus stops very convenient for what we did on our trip. The host was very accommodating and left great instructions on how to access the home. "
United States
Stephen M.
Hamaline Luxury - Guest House

1 #31 - 4 Bedroom Condo - McCormick Place, Wintrust Arena, Chinatown

Chinatown
9.8 out of 10, Exceptional, (9)
"Just off the red line. Plenty of great food near by"
United States
Steve C.
1 #31 - 4 Bedroom Condo - McCormick Place, Wintrust Arena, Chinatown

4 #2N - 4 Bedroom / 4 Bath Condo - McCormick Place, Wintrust Arena, Chinatown

Armour Square
9.2 out of 10, Wonderful, (13)
"Enjoyed the neighborhood "
United States
Nicole P.
4 #2N - 4 Bedroom / 4 Bath Condo - McCormick Place, Wintrust Arena, Chinatown

Spacious 2BR Unit with Skyline View Near McCormick Place & Soldier Field

Near South Side
9.4 out of 10, Exceptional, (3)
"We enjoyed our weekend in Chicago. Location was easy to get to from the airports, building was secure and the host was great to work with. Great place. "
United States
Greg F.
Spacious 2BR Unit with Skyline View Near McCormick Place & Soldier Field

Modern 4 Bed, 3.5 Bath Home | Near Sox & McCormick

Bronzeville
10.0 out of 10, Exceptional, (6)
"We were preparing for our organizations annual fundraiser gala. This home was absolutely amazing. The space was appreciated. "
United States
Nancy M.
Modern 4 Bed, 3.5 Bath Home | Near Sox & McCormick

McCormick Apt 3BR Corner Oasis Near Soldier Field & Museum Campus

Near South Side
McCormick Apt 3BR Corner Oasis Near Soldier Field & Museum Campus

Breeze of Bronzeville Chicago: 3 bedroom 2 bath 9 mins from downtown chicago

Bronzeville
7.6 out of 10, Good, (4)
"The place was nice!!!! Joseph( Host) Has great communication skills!!!! The place felt like a nice hideout getaway and nice neighborhood. I would love to come back. Thanks for the stay!!!"
United States
Dante' M.
Breeze of Bronzeville Chicago: 3 bedroom 2 bath 9 mins from downtown chicago

LuxHome up to 6 guests in Chicago; WiFi, AC, Heat, Security cams, Downtown 8mins

Bronzeville
9.4 out of 10, Exceptional, (11)
"Property matched the pictures perfectly! Loved the updates and appreciated the abundance of towels, dishes, etc! 3rd floor walkup if thats an issue for you. Also felt safe and secure. Great neighborhood too! Host provided detailed, easy to understand instructions for the property and was accessible via the VRBO app! "
United States
Marquita S.
LuxHome up to 6 guests in Chicago; WiFi, AC, Heat, Security cams, Downtown 8mins

Ahh-mazing Home, rooftop deck, near lake front. Easy commute to Navy Pier/Loop.

Kenwood
6.0 out of 10, (2)
"Great property"
United States
Anonymous traveler
Ahh-mazing Home, rooftop deck, near lake front. Easy commute to Navy Pier/Loop.

Modern 3BR Near McCormick & South Loop

Near South Side
Modern 3BR Near McCormick & South Loop

Spacious 3BR Urban Getaway w Gym

Near South Side
Spacious 3BR Urban Getaway w Gym

Stylish 3BR Gem in Prime Location

Near South Side
Stylish 3BR Gem in Prime Location
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 27th Street Station Hotel Reviews

Find out more about Chicago 27th Street Station

What types of Vacation Homes can I find in Chicago 27th Street Station?

At Expedia, you’ll find great Chicago 27th Street 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 27th Street 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 27th Street Station. While you’re making your decision, you can use our map facility to view your shortlisted properties and their distance from Chicago 27th Street Station, or nearby places of interest. There are great places to stay for every budget, so if you need cheap Vacation Homes in Chicago 27th Street Station, use our simple search function to help you secure a great deal.

How much do Vacation Homes cost in Chicago 27th Street Station?

The price per night for Chicago 27th Street 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 27th Street Station, to name just three. When there’s a high demand for rooms in Chicago 27th Street 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 27th Street Station, so you can sleep easy without going over your budget.

How to find the best deals on Chicago 27th Street Station Vacation Homes?

Expedia’s search function can help you find some of the best deals on Chicago 27th Street 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 27th Street 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.

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Booking with Expedia allows you to browse a wide selection of places to stay in Chicago 27th Street 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 27th Street Station Vacation Homes?

At Expedia, we understand that plans change, and the good news is you can cancel many bookings for Chicago 27th Street 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 27th Street 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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