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Our top choices for Jackson Station (Red Line) condo rentals

Brilliant Downtown Chicago 3-Bedroom Condominium

Brilliant Downtown Chicago 3-Bedroom Condominium
Downtown Chicago
10.0 out of 10, Exceptional, (52 reviews)
"Great location and perfect layout for a girls trip. "
United States
Brigitte H.
Brilliant Downtown Chicago 3-Bedroom Condominium

Downtown Penthouse Huge Patio with Great View

Downtown Penthouse Huge Patio with Great View
Downtown Chicago
10.0 out of 10, Exceptional, (2 reviews)
"Great stay at a wonderful property. Hosts were very friendly and helpful. I recommend this property"
United States
Dave L.
Downtown Penthouse Huge Patio with Great View

Gorgeous 3BR River North Condo - Free Parking

Gorgeous 3BR River North Condo - Free Parking
Downtown Chicago
10.0 out of 10, Exceptional, (31 reviews)
"Amazing location! "
United States
Justin H.
Gorgeous 3BR River North Condo - Free Parking

MAG MILE MEGA Entire Floor 4BD 4BA +Rooftop&Gym

MAG MILE MEGA Entire Floor 4BD 4BA +Rooftop&Gym
Downtown Chicago
9.4 out of 10, Exceptional, (31 reviews)
"Shower was broken in main bathroom, needed a little updating Great location!"
United States
linda n.
MAG MILE MEGA Entire Floor 4BD 4BA +Rooftop&Gym

MICH AVE #5|Safe DTown Grant Park, Museums 2bd/2ba

MICH AVE #5|Safe DTown Grant Park, Museums 2bd/2ba
Near South Side
9.8 out of 10, Exceptional, (28 reviews)
"We had a great stay at this apartment in Chicago. The location was excellent for tourists and the place was clean and safe. We would stay here again. "
United States
Carlos C.
MICH AVE #5|Safe DTown Grant Park, Museums 2bd/2ba

Near Fulton Market! Walkable West Loop Condo

Near Fulton Market! Walkable West Loop Condo
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"Such a lovely place to stay! The location was fantastic—within walking distance of Fulton Market, a lively district filled with great restaurants and shops. We had brunch at The Oakville and loved the ambiance and delicious food.The space was clean, bright, and surprisingly spacious. The beds and linens were incredibly comfortable, and having two bathrooms was a huge plus. The bath products even smelled amazing!The kitchen was fully stocked with all the cookware we needed for a cozy night in,...
United States
Lorie
Near Fulton Market! Walkable West Loop Condo

MICH AVE Downtown 2bd, Grant Park Museums #25

MICH AVE Downtown 2bd, Grant Park Museums #25
Downtown Chicago
9.8 out of 10, Exceptional, (31 reviews)
"Amazing location, good communication, would definitely come back."
United States
Adam M.
MICH AVE Downtown 2bd, Grant Park Museums #25

Go Grand in This Massive Old Town Mansion by AllSet Turnover

Go Grand in This Massive Old Town Mansion by AllSet Turnover
Near North Side
9.6 out of 10, Exceptional, (4 reviews)
"Great property for large groups, everyone had their own room and bathroom. Lots of stairs and the AC can’t quite keep up in exceptionally hot days but neither would turn me off from staying again."
United States
Brandon M.
Go Grand in This Massive Old Town Mansion by AllSet Turnover

Luxury 4BD Gold Coast Penthouse with Deck & Views

Luxury 4BD Gold Coast Penthouse with Deck & Views
Downtown Chicago
10.0 out of 10, Exceptional, (2 reviews)
"this property is in an outstanding location, surrounded by restaurants, bars, stores etc. The only drawbacks were the lack of any coffee making items and a shortage of glasses. Otherwise it is a great spot."
United States
Doug H.
Luxury 4BD Gold Coast Penthouse with Deck & Views

Downtown MICH AVE #20, Grant Park, Museums 2bd/2ba

Downtown MICH AVE #20, Grant Park, Museums 2bd/2ba
Near South Side
10.0 out of 10, Exceptional, (11 reviews)
"Convenient location to my convention at McCormack Place by day and dinner at great restaurants by night. Clean, comfortable and safe spot. "
United States
James K.
Downtown MICH AVE #20, Grant Park, Museums 2bd/2ba

Downtown 2bd #4 - Near Grant Park, Museums, Lake

Downtown 2bd #4 - Near Grant Park, Museums, Lake
Downtown Chicago
10.0 out of 10, Exceptional, (4 reviews)
"Loved coming back to the place after a long day exploring Chicago, easy to get to from just about anywhere. Felt comforting and homey."
United States
Remington G.
Downtown 2bd #4 - Near Grant Park, Museums, Lake

Two-Story STUNNER in Iconic Old Town Chicago by AllSet Turnover

Two-Story STUNNER in Iconic Old Town Chicago by AllSet Turnover
Near North Side
9.0 out of 10, Wonderful, (18 reviews)
"Comfortable and clean in an excellent location. Short walk to all the Old Town locations like Second City, Chicago History Museum and all the restaurants and stores along Wells St. well equipped and comfortable bed, lots of space in a quiet building. We enjoyed our stay here. "
United States
Sue C.
Two-Story STUNNER in Iconic Old Town Chicago by AllSet Turnover

Downtown Lake VIEWS, Mich Ave, Museums 2bd/2ba

Downtown Lake VIEWS, Mich Ave, Museums 2bd/2ba
Near South Side
9.8 out of 10, Exceptional, (47 reviews)
"Apartment was clean. Location was great. I have rented several homes over the years and this owner went above and beyond. Best experience I have ever had. I would not hesitate to rent again."
United States
Michelle
Downtown Lake VIEWS, Mich Ave, Museums 2bd/2ba

Downtown Penthouse Lake Views #1|Gym, Parking+Pool

Downtown Penthouse Lake Views #1|Gym, Parking+Pool
Downtown Chicago
10.0 out of 10, Exceptional, (4 reviews)
"The views are even more amazing in person. The listing doesn't show how terrific the view is of the lakeshore & downtown."
United States
Nancy M.
Downtown Penthouse Lake Views #1|Gym, Parking+Pool

Downtown 3bd #7 near Park+Museums

Downtown 3bd #7 near Park+Museums
Downtown Chicago
10.0 out of 10, Exceptional, (6 reviews)
"Fantastic location, close to everything, with plenty of space for 3 couples"
United States
Steve S.
Downtown 3bd #7 near Park+Museums

Cozy Downtown MICH AVE #7 | gym+rooftop

Cozy Downtown MICH AVE #7 | gym+rooftop
Downtown Chicago
9.8 out of 10, Exceptional, (10 reviews)
"Great location...host quick response..."
United States
Tricia N.
Cozy Downtown MICH AVE #7 | gym+rooftop

Designer Loft in Fulton Market with Parking

Designer Loft in Fulton Market with Parking
Downtown Chicago
10.0 out of 10, Exceptional, (7 reviews)
"Beautiful condo! Great location. "
United States
Megan W.
Designer Loft in Fulton Market with Parking

Downtown 2bd #6 +Gym near Park, Lake, Museums

Downtown 2bd #6 +Gym near Park, Lake, Museums
Downtown Chicago
10.0 out of 10, Exceptional, (3 reviews)
"Clean and comfortable. Great location for walking to museums and parks. "
United States
John D.
Downtown 2bd #6 +Gym near Park, Lake, Museums

Downtown Park #11 - Mich Ave PH | gym+rooftop

Downtown Park #11 - Mich Ave PH | gym+rooftop
Downtown Chicago
9.0 out of 10, Wonderful, (6 reviews)
"Great location for Art In field mu"
United States
Carl C.
Downtown Park #11 - Mich Ave PH | gym+rooftop

Downtown Penthouse - Mich Ave 2bd | +gym & VIEWS

Downtown Penthouse - Mich Ave 2bd | +gym & VIEWS
Downtown Chicago
9.8 out of 10, Exceptional, (32 reviews)
"Very easy check in- all the details were sent in advance. Fantastic location."
United States
Thomas B.
Downtown Penthouse - Mich Ave 2bd | +gym & VIEWS
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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What types of Condo Rentals can I find in Jackson Station?

At Expedia, you’ll find great Jackson Station Condo Rentals 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” Jackson Station Condo Rentals. Or, if you’re traveling for work, you can check the “Business-friendly” box to find business-oriented places to stay in Jackson Station. While you’re making your decision, you can use our map facility to view your shortlisted properties and their distance from Jackson Station, or nearby places of interest. There are great places to stay for every budget, so if you need cheap Condo Rentals in Jackson Station, use our simple search function to help you secure a great deal.

How much do Condo Rentals cost in Jackson Station?

The price per night for Jackson Station Condo Rentals in 2026 can start from as low as *. The cost of Condo Rentals 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 Jackson Station, to name just three. When there’s a high demand for rooms in Jackson 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 Condo Rentals in Jackson Station, so you can sleep easy without going over your budget.

How to find the best deals on Jackson Station Condo Rentals?

Expedia’s search function can help you find some of the best deals on Jackson Station Condo Rentals. 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 Condo Rentals for your needs. Changing the sort order according to price can also help you to view cheap Condo Rentals in Jackson 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 Jackson Station, complete with search filters that make it easy to locate Condo Rentals 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 Jackson Station Condo Rentals?

At Expedia, we understand that plans change, and the good news is you can cancel many bookings for Jackson Station Condo Rentals with a full refund, depending on the rules and restrictions. For example, some Condo Rentals 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 Jackson Station Condo Rentals, 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 Condo Rentals.

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

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