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Central Chicago Vacation Rentals

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Check prices for these dates

In two weeks
Dec 19 - Dec 21
In two months
Jan 30 - Feb 1
In three months
Feb 27 - Mar 1
In four months
Mar 27 - Mar 29

Vacation Rentals in Central Chicago

Indoor pool
Sentral Michigan Avenue

Aparthotel in Downtown Chicago

4.0 star property
9.2 out of 10, Wonderful, (997)
"Loved my stay! Staff was amazing and the apartment had everything to make you feel like home. "
United States
Nicole
$196 nightly
The price is $230
Dec 7 - Dec 8
Total with taxes and fees
Sentral Michigan Avenue
Front of property - evening/night
Level Chicago – Old Town

Aparthotel in Downtown Chicago

4.0 star property
9.0 out of 10, Wonderful, (392)
"Clean room cool staff enjoyed my stay will come stay again. "
United States
Donald
$215 nightly
The price is $252
Dec 17 - Dec 18
Total with taxes and fees
Level Chicago – Old Town
49-inch Smart TV with digital channels, TV, streaming services
Kasa Magnificent Mile Chicago

Aparthotel in Downtown Chicago

4.0 star property
9.2 out of 10, Wonderful, (642)
"Clean facilities, great staff, good location "
United States
Emily
Kasa Magnificent Mile Chicago
Deluxe Apartment, 1 Bedroom, Non Smoking, Balcony (Self Check-in with Virtual Front Desk) | Balcony
Kasa South Loop Chicago

Aparthotel in Downtown Chicago

4.0 star property
9.4 out of 10, Exceptional, (379)
"A very clean and spacious apartment with a great view. The parking garage right next to the building is very convenient. If the water pressure be improved, that will be perfect."
United States
Tammy
Kasa South Loop Chicago
Free WiFi, bed sheets
Chicago luxury home suites

Aparthotel in Downtown Chicago

2.0 star property
10.0 out of 10, Exceptional, (2)
"Great service and communication throughout my entire stay. Very clean and easy to access to everything that i needed. Even though it was a short stay but had a comfortable and pleasant stay. Everything was available for me before i arrived. Thank you really. Great job."
Canada
pouya
$132 nightly
The price is $156
Dec 7 - Dec 8
Total with taxes and fees
Chicago luxury home suites
Business center
Kasa River North Chicago

Aparthotel in Downtown Chicago

4.0 star property
9.4 out of 10, Exceptional, (180)
"Awesome stay "
United States
Sally
$347 nightly
The price is $407
Dec 7 - Dec 8
Total with taxes and fees
Kasa River North Chicago
Interior
Twice as Nice: Chic 2BR Stay with Style & Space

Apartment in Downtown Chicago

9.6 out of 10, Exceptional, (14)
"Host was easy to communicate with and very thoughtful. We were in town for a concert and they gifted us with ear protection for us all. Location was great too "
United States
Tiffany N.
$167 nightly
The price is $182
Dec 7 - Dec 8
Total with taxes and fees
Twice as Nice: Chic 2BR Stay with Style & Space
Terrace/patio
Chicago Luxury Penthouse Gold Coast Best Location

Condo in Downtown Chicago

10.0 out of 10, Exceptional, (3)
"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."
United States
Justin F.
Chicago Luxury Penthouse Gold Coast Best Location
Interior
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars

Vacation Home in Near North Side

9.4 out of 10, Exceptional, (105)
"Awesome space for our large group! Location couldn’t have been better - on a very nice street with tons of bars and restaurants near by."
United States
Elias P.
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars
Dining
55-56 Mag Mile Penthouse

Apartment in Downtown Chicago

10.0 out of 10, Exceptional, (300)
"Great location, great property, great views. "
United States
Mark D.
55-56 Mag Mile Penthouse
Terrace/patio
Chicago Gold Coast Luxury Home Best Location walking distance to anywhere!

Vacation Home in Downtown Chicago

10.0 out of 10, Exceptional, (25)
"I cannot express how wonderful the stay was! From the communication level of the hosts to the details and cleanliness let alone the beauty of this home, it was absolutely wonderful in every way! We will absolutely be staying here again for any future needs!"
United States
Erica S.
Chicago Gold Coast Luxury Home Best Location walking distance to anywhere!
Indoor pool
Luxury Penthouse: Iconic Views + Exclusive Comfort

Apartment in Downtown Chicago

10.0 out of 10, Exceptional, (6)
"Very clean, nice views in a safe area and within walking distance of so many great attractions!"
United States
Gary
Luxury Penthouse: Iconic Views + Exclusive Comfort
Interior
Your Chicago get Away

Apartment in Downtown Chicago

8.4 out of 10, Very Good, (8)
"Clean, fun space and responsive host! Loved the views from our room!"
United States
Tyler C.
$389 nightly
The price is $426
Dec 11 - Dec 12
Total with taxes and fees
Your Chicago get Away
Pool
52nd Floor MagMile Penthouse VIEWS Fireplace Pool

Apartment in Downtown Chicago

10.0 out of 10, Exceptional, (404)
"Great place great location and easy to contact owners and check in. Amenities are great too."
United States
Kai A.
52nd Floor MagMile Penthouse VIEWS Fireplace Pool
Interior
Gold Coast Living: Modern Studio Unit

Apartment in Downtown Chicago

10.0 out of 10, Exceptional, (4)
"The communication was really effective and made for a smooth check in and check out process. Host was friendly and made great recommendations, 10/10 would stay again!"
United States
Seynabou
$149 nightly
The price is $166
Jan 1 - Jan 2, 2026
Total with taxes and fees
Gold Coast Living: Modern Studio Unit
Fridge, microwave, oven, stovetop
Gilded Age Gold Coast Mansion with Parking, Deck, Fireplaces

Vacation Home in Downtown Chicago

10.0 out of 10, Exceptional, (6)
"We had a great stay! Inna provided us all the info we needed to check in smoothly when we arrived and the garage spot made it easy for us to park and unload luggage straight into the house. Everything was super clean! The house is big enough that even with so many guests everyone felt spread out and had their own space. We were able to take a 5ish min walk to the beach which was such a bonus! "
United States
Raleigh H.
Gilded Age Gold Coast Mansion with Parking, Deck, Fireplaces
Pool
Luxury 2BR on Michigan Ave with Private Balcony

Apartment in Downtown Chicago

9.8 out of 10, Exceptional, (16)
"Great place and attentive hosts. "
United States
Carol L.
Luxury 2BR on Michigan Ave with Private Balcony
Outdoor dining
Spacious 4BR Central Apartment w/ Skyline Views

Apartment in Near North Side

10.0 out of 10, Exceptional, (7)
Spacious 4BR Central Apartment w/ Skyline Views
Fridge, microwave, oven, dishwasher
Two-Story STUNNER in Iconic Old Town Chicago by AllSet Turnover

Condo in Near North Side

9.4 out of 10, Exceptional, (17)
"It was a very lovely and well-appointed place for my family to stay. The separate TV area was especially nice for traveling with our young son. "
United States
Erin D.
Two-Story STUNNER in Iconic Old Town Chicago by AllSet Turnover
Fridge, microwave, oven, stovetop
Brownstone in Gold Coast - Downtown

Apartment in Downtown Chicago

9.6 out of 10, Exceptional, (30)
"We had a great stay at this brownstone! It’s in a great location and walkable to many different restaurants and Miracle Mile! "
United States
Moncy N.
Brownstone in Gold Coast - Downtown
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

The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

10/10 Excellent
"Very nice staff, beautiful hotel and a clean room"
Tara 3-night trip
Posted 8 hours ago
The Royal Sonesta Chicago Downtown

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 $156 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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