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Central Chicago Vacation Rentals

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Check prices for these dates

In two weeks
Jul 17 - Jul 19
In two months
Aug 28 - Aug 30
In three months
Sep 25 - Sep 27
In four months
Oct 23 - Oct 25

Our top choices for Central Chicago vacation rentals

Indoor pool

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,200 reviews)
"Great location"
United States
JAVIER
$177 nightly
The price is $208
Jul 5 - Jul 6
Total with taxes and fees
Sentral Michigan Avenue
Full-size fridge, microwave, oven, stovetop

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (497 reviews)
"Very clean and loved the location and amenities with the store on the first floor was fantastic"
United States
Kimberly
$299 nightly
The price is $351
Jul 6 - Jul 7
Total with taxes and fees
Level Chicago – Old Town
Property grounds

ENVITAE Hotel, 4BR Luxury Modern Apartments

ENVITAE Hotel, 4BR Luxury Modern Apartments
Near North Side
9.6 out of 10, Exceptional, (14 reviews)
"The property was clean and the location was great."
United States
Steven C.
$476 nightly
The price is $587
Jul 8 - Jul 9
Total with taxes and fees
ENVITAE Hotel, 4BR Luxury Modern Apartments
TV, offices

LIVN Millennium Park Downtown Chicago 2BR

LIVN Millennium Park Downtown Chicago 2BR
Downtown Chicago
10.0 out of 10, Exceptional, (5 reviews)
"Excellent location... Very cleaned....it is perfect"
United States
Granada
$208 nightly
The price is $246
Jul 6 - Jul 7
Total with taxes and fees
LIVN Millennium Park Downtown Chicago 2BR
Lounge

Kasa River North Chicago

Kasa River North Chicago
4.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (197 reviews)
"Great property - would come back. Decent size rooms and generally good all around"
United States
Suyash
Kasa River North Chicago
Interior

River North Rooftop With In and Out Parking 3

River North Rooftop With In and Out Parking 3
Downtown Chicago
9.8 out of 10, Exceptional, (7 reviews)
"We had a very comfortable stay here. The hosts are exceptionally communicative and helpful. Loved having a place to park my car, and the hosts set it up so my license plate was recognized at the gate so that parking was free. The unit was very clean and spacious. Note, the kitchen does not have pots or pans to cook, so plan on eating out!"
United States
Jennifer M.
$525 nightly
The price is $601
Jul 6 - Jul 7
Total with taxes and fees
River North Rooftop With In and Out Parking 3
Interior

Premium Urban 4BR - Perfect Mix of Comfort & Location

Premium Urban 4BR - Perfect Mix of Comfort & Location
Near North Side
10.0 out of 10, Exceptional, (1 review)
"Nice place, clean property, great views "
United States
Zach L.
$627 nightly
The price is $774
Jul 9 - Jul 10
Total with taxes and fees
Premium Urban 4BR - Perfect Mix of Comfort & Location
Pool

South Loop Rooftop With In and Out Parking 2

South Loop Rooftop With In and Out Parking 2
Downtown Chicago
10.0 out of 10, Exceptional, (2 reviews)
"Great place to stay! Parking was easy and secure. The building was super clean and had lots of amenities. Host was very responsive to messages and very accommodating to our last minute schedule changes. "
United States
Kara V.
$638 nightly
The price is $740
Jul 17 - Jul 18
Total with taxes and fees
South Loop Rooftop With In and Out Parking 2
TV, offices

LIVN Millennium Park Downtown Chicago 1 BR

LIVN Millennium Park Downtown Chicago 1 BR
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"Great location to sights, shops, and food."
United States
Adrianna W.
$170 nightly
The price is $201
Jul 5 - Jul 6
Total with taxes and fees
LIVN Millennium Park Downtown Chicago 1 BR
TV, offices

LIVN Millennium Park Downtown Chicago Superior 1BR

LIVN Millennium Park Downtown Chicago Superior 1BR
Downtown Chicago
10.0 out of 10, Exceptional, (2 reviews)
"Excelente, well located. Recommended."
United States
Sandra S.
$164 nightly
The price is $194
Jul 5 - Jul 6
Total with taxes and fees
LIVN Millennium Park Downtown Chicago Superior 1BR
Dining

LIVN Millennium Park Downtown Chicago Studio

LIVN Millennium Park Downtown Chicago Studio
Downtown Chicago
10.0 out of 10, Exceptional, (3 reviews)
"Great location, lovely furnishings and amenities."
United States
Georgina E.
$174 nightly
The price is $205
Jul 5 - Jul 6
Total with taxes and fees
LIVN Millennium Park Downtown Chicago Studio
Dining

LIVN Millennium Park Downtown Chicago Prem Studio

LIVN Millennium Park Downtown Chicago Prem Studio
Downtown Chicago
10.0 out of 10, Exceptional, (3 reviews)
"The check in and out process was very quick. Communication with the host was great. "
United States
Raquel W.
$170 nightly
The price is $201
Jul 5 - Jul 6
Total with taxes and fees
LIVN Millennium Park Downtown Chicago Prem Studio
TV, offices

LIVN Millennium Park Downtown Chicago Superior 2 BR

LIVN Millennium Park Downtown Chicago Superior 2 BR
Downtown Chicago
9.6 out of 10, Exceptional, (4 reviews)
"We loved the location."
United States
Nicoll M.
$190 nightly
The price is $224
Jul 5 - Jul 6
Total with taxes and fees
LIVN Millennium Park Downtown Chicago Superior 2 BR
TV, offices

South Loop Rooftop With In and Out Parking 3

South Loop Rooftop With In and Out Parking 3
Downtown Chicago
8.8 out of 10, Excellent, (5 reviews)
"Clean place. Family friendly. Location was great. A lot of restaurants close by. Great communication from the host."
United States
jaspreet
$547 nightly
The price is $628
Aug 3 - Aug 4
Total with taxes and fees
South Loop Rooftop With In and Out Parking 3
Exterior

Spacious 4BR Central Apartment w/ Skyline Views

Spacious 4BR Central Apartment w/ Skyline Views
Near North Side
10.0 out of 10, Exceptional, (24 reviews)
"Great place! The location is perfect. The apartment was comfortable for 5 people. Love the king beds in each room.It was clean and the staff was very helpful.Would definitely stay here again!"
United States
valerie h.
$1,536 nightly
The price is $1,895
Jul 31 - Aug 1
Total with taxes and fees
Spacious 4BR Central Apartment w/ Skyline Views
Fridge, microwave, oven, stovetop

Stylish friendly 3BR Suite near McCormick

Stylish friendly 3BR Suite near McCormick
Near South Side
$417 nightly
The price is $465
Jul 5 - Jul 6
Total with taxes and fees
Stylish friendly 3BR Suite near McCormick
2 bedrooms, desk, iron/ironing board, travel crib

South Loop Rooftop With In & Out Parking 1

South Loop Rooftop With In & Out Parking 1
Downtown Chicago
9.0 out of 10, Wonderful, (2 reviews)
"We loved the property! It was well kept, clean, with a seamless check in and check out process! I wish the parking garage would have been closer but otherwise everything was great! Shout out to the host for his promptness with all my questions! I would recommend this place if they are looking for a place to stay! "
United States
Bridney K.
$609 nightly
The price is $705
Jul 29 - Jul 30
Total with taxes and fees
South Loop Rooftop With In & Out Parking 1
Interior

McCormick 4BR Huge Unit w/ Pool Table | Sleeps 11

McCormick 4BR Huge Unit w/ Pool Table | Sleeps 11
Near South Side
$387 nightly
The price is $432
Jul 6 - Jul 7
Total with taxes and fees
McCormick 4BR Huge Unit w/ Pool Table | Sleeps 11
3 bedrooms, iron/ironing board, travel crib, WiFi

3BR · Steps from McCormick · Balcony & Gym

3BR · Steps from McCormick · Balcony & Gym
Near South Side
9.6 out of 10, Exceptional, (5 reviews)
"Six of us made a trip to Chicago and stayed at this location. The place is very roomy with a full kitchen. There was public transportation nearby to get us ro everywhere we were going ( Field museum, Grant park, Navy pier)."
United States
Kathy
$389 nightly
The price is $480
Jul 8 - Jul 9
Total with taxes and fees
3BR · Steps from McCormick · Balcony & Gym
Interior

Chicago Spacious 3Br Smoke Ok Near McCormick Place

Chicago Spacious 3Br Smoke Ok Near McCormick Place
Near South Side
$331 nightly
The price is $370
Jul 5 - Jul 6
Total with taxes and fees
Chicago Spacious 3Br Smoke Ok Near McCormick Place
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

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

10/10 Excellent
"Breakfast buffet was amazing"
Patrick Dean 3-night trip
Posted less than an hour ago
Hotel Riu Plaza 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 $208 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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