Central Chicago Vacation Rentals

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In two weeks
Sep 12 - Sep 14
In one month
Sep 26 - Sep 28
In two months
Oct 24 - Oct 26
In three months
Nov 21 - Nov 23

Vacation Rentals in Central Chicago

Sentral Michigan Avenue
Interior

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (899)
"great food spots all around and beautiful sites to see "
$160 nightly
The price is $188
Sep 2 - Sep 3
Total with taxes and fees
Sentral Michigan Avenue
Kasa Magnificent Mile Chicago
49-inch Smart TV with digital channels, TV, streaming services

Kasa Magnificent Mile Chicago

4.0 star property
9.2 out of 10, Wonderful, (487)
"It was a great property to stay at, definitely would book again! "
Kasa Magnificent Mile Chicago
Level Chicago – Old Town
Front of property - evening/night

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (345)
"A lot of good food options walkable distance. "
$242 nightly
The price is $285
Sep 1 - Sep 2
Total with taxes and fees
Level Chicago – Old Town
Sonder by Marriott Bonvoy South Wabash Apartments South Loop
36-inch flat-screen TV with digital channels, TV

Sonder by Marriott Bonvoy South Wabash Apartments South Loop

3.5 star property
8.8 out of 10, Excellent, (635)
"Loved this apartment style stay near everything we wanted to visit in Chicago. "
$149 nightly
The price is $175
Sep 2 - Sep 3
Total with taxes and fees
Sonder by Marriott Bonvoy South Wabash Apartments South Loop
Kasa South Loop Chicago
Deluxe Apartment, 1 Bedroom, Non Smoking, Balcony (Self Check-in with Virtual Front Desk) | Balcony

Kasa South Loop Chicago

4.0 star property
9.4 out of 10, Exceptional, (334)
"Amazing!"
Kasa South Loop Chicago
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
50-inch flat-screen TV with digital channels, TV

Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

3.5 star property
8.2 out of 10, Very Good, (177)
"Great location!!!"
$149 nightly
The price is $175
Sep 2 - Sep 3
Total with taxes and fees
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
Sonder by Marriott Bonvoy The Opal Apartments River North
1 bedroom, individually furnished, desk, iron/ironing board

Sonder by Marriott Bonvoy The Opal Apartments River North

3.5 star property
8.4 out of 10, Very Good, (47)
"Great location. Apartment had all the amenities needed. Felt safe. Only not so good part was that being in downtown, it wasn't super quiet at times. Would stay here again without a doubt."
$169 nightly
The price is $199
Sep 28 - Sep 29
Total with taxes and fees
Sonder by Marriott Bonvoy The Opal Apartments River North
Kasa River North Chicago
Business center

Kasa River North Chicago

4.0 star property
9.6 out of 10, Exceptional, (166)
"This place has everything for a multi-night stay."
$264 nightly
The price is $310
Sep 2 - Sep 3
Total with taxes and fees
Kasa River North Chicago
Sonder by Marriott Bonvoy The Plymouth Apartments Loop
Property amenity

Sonder by Marriott Bonvoy The Plymouth Apartments Loop

3.5 star property
7.8 out of 10, Good, (133)
"Super convenient location. Lots of parking options and able to walk to all sites in this area."
$189 nightly
The price is $222
Sep 1 - Sep 2
Total with taxes and fees
Sonder by Marriott Bonvoy The Plymouth Apartments Loop
Your Chicago get Away
Interior

Your Chicago get Away

10.0 out of 10, Exceptional, (2)
"Clean, fun space and responsive host! Loved the views from our room!"
$485 nightly
The price is $546
Sep 18 - Sep 19
Total with taxes and fees
Your Chicago get Away
Chicago Luxury Penthouse Massive Rooftop Walk to Beach and Restaurants
Terrace/patio

Chicago Luxury Penthouse Massive Rooftop Walk to Beach and Restaurants

10.0 out of 10, Exceptional, (2)
"I used to live in Chicago and have a short term rental in Ohio myself. This place is legit. This property is in the best location close to beach restaurants and bars. Perfect for college reunion. Rooftop was awesome place for us to catch up over coffee and plan the day. The kitchen has everything we needed. Speakers throughout was a nice touch. I can’t be more complementary of the hosts responsiveness and helpfulness. We would definitely stay here again."
Chicago Luxury Penthouse Massive Rooftop Walk to Beach and Restaurants
Walk Everywhere! 5 mins to Magnificent Mile, River
TV, offices

Walk Everywhere! 5 mins to Magnificent Mile, River

10.0 out of 10, Exceptional, (2)
"Excellent "
Walk Everywhere! 5 mins to Magnificent Mile, River
Gorgeous 3BR River North Condo - Free Parking
Fridge, microwave, oven, stovetop

Gorgeous 3BR River North Condo - Free Parking

10.0 out of 10, Exceptional, (20)
"Great location, beautiful home, host was very friendly and easy to communicate with! Would definitely recommend this home!!"
Gorgeous 3BR River North Condo - Free Parking
Michigan Ave 2BR: Balcony, Exclusive Access
Pool

Michigan Ave 2BR: Balcony, Exclusive Access

9.6 out of 10, Exceptional, (13)
"We use to live in Chicago and knew that this was a perfect location. And it still is. The hosts communication was top-notch, the place was as described, and everything was beyond clean. Highly highly recommend!"
Michigan Ave 2BR: Balcony, Exclusive Access
McCormick Place Oasis 2br/2ba with optional Parking/Patio/Gym/sleeps 6
Terrace/patio

McCormick Place Oasis 2br/2ba with optional Parking/Patio/Gym/sleeps 6

9.0 out of 10, Wonderful, (2)
"Overall stay, I would rate a 4.2 out of 5. The host was very responsive. The only problems I did encounter was parking, the inconsistency of the thermostat, and beds. Overall I would book again. So that should say a lot. "
McCormick Place Oasis 2br/2ba with optional Parking/Patio/Gym/sleeps 6
Stylish 4BR Stay-Prime Location - State rep
4 bedrooms, iron/ironing board, travel crib, WiFi

Stylish 4BR Stay-Prime Location - State rep

10.0 out of 10, Exceptional, (1)
"Incredibly clean and spacious apartment. The beds were comfortable, and we really appreciated having multiple bathrooms. The kitchen was well stocked and the location was a short Lyft/uber from everywhere we wanted to be. Would definitely stay here again."
$369 nightly
The price is $401
Sep 2 - Sep 3
Total with taxes and fees
Stylish 4BR Stay-Prime Location - State rep
Luxury House in the heart of Old Town with Parking
Interior

Luxury House in the heart of Old Town with Parking

10.0 out of 10, Exceptional, (50)
"We stayed for a number of weeks at the property - it was an excellent stay! The property is exactly as advertised and the owner was extremely helpful, communicative, and responsive throughout. The house is modern, in good condition, and is an excellent location."
Luxury House in the heart of Old Town with Parking
2nd Floor Flat in River North - 2S
Property grounds

2nd Floor Flat in River North - 2S

9.8 out of 10, Exceptional, (22)
"Beautiful space! Wonderful stay! Perfect location!"
2nd Floor Flat in River North - 2S
Studio flat in the heart of Chicago's Gold Coast
Fridge, microwave, oven, stovetop

Studio flat in the heart of Chicago's Gold Coast

9.6 out of 10, Exceptional, (10)
"The property is in downtown and very close to everything "
Studio flat in the heart of Chicago's Gold Coast
Modern 2b/2b family heaven with optional parking for up to 8 guests
Exterior

Modern 2b/2b family heaven with optional parking for up to 8 guests

9.2 out of 10, Wonderful, (5)
"Short walk to McCormick place. Would stay again."
Modern 2b/2b family heaven with optional parking for up to 8 guests
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 Central Chicago Hotel Reviews

Find out more about Central Chicago

Find out more about Central Chicago

Everything you need to know about Central Chicago vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Central Chicago vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Central Chicago vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Central Chicago vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Central Chicago. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Central Chicago in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $175 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Central Chicago rentals

At Expedia, we put the best Central Chicago vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Central Chicago rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Central Chicago vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Central Chicago. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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Explore a world of travel with Expedia