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Chicago Vacation Rentals

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Check prices for these dates

In two weeks
Jul 31 - Aug 2
In two months
Sep 11 - Sep 13
In three months
Oct 9 - Oct 11
In four months
Nov 6 - Nov 8

Our top choices for Chicago vacation rentals

Private kitchen

Charming 2-bedroom apartment with AC in fantastic Chicago

Charming 2-bedroom apartment with AC in fantastic Chicago
Downtown Chicago
Charming 2-bedroom apartment with AC in fantastic Chicago
Indoor pool

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,215 reviews)
"Clean room, great staff, family-friendly, pet-friendly, and great rooms with a kitchen and wonderful showers. Great location!"
United States
Alessandra
$200 nightly
The price is $235
Aug 9 - Aug 10
Total with taxes and fees
Sentral Michigan Avenue
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.
$354 nightly
The price is $418
Jul 20 - Jul 21
Total with taxes and fees
LIVN Millennium Park Downtown Chicago Superior 1BR
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, (501 reviews)
"Overall, I had a pleasant stay. The room was clean, and the staff were helpful. The property was comfortable and family-friendly. The only improvement would be better Wi-Fi and more breakfast options. I would still recommend this place."
United States
Serigne abdou
$372 nightly
The price is $437
Aug 13 - Aug 14
Total with taxes and fees
Level Chicago – Old Town
1 bedroom, iron/ironing board, travel crib, WiFi

LIVN West Loop Chicago Classic Queen Studio

LIVN West Loop Chicago Classic Queen Studio
Downtown Chicago
10.0 out of 10, Exceptional, (6 reviews)
$187 nightly
The price is $221
Jul 19 - Jul 20
Total with taxes and fees
LIVN West Loop Chicago Classic Queen Studio
TV, offices

Modern West Loop Gem-City Views & Prime Location 5

Modern West Loop Gem-City Views & Prime Location 5
Downtown Chicago
9.0 out of 10, Wonderful, (6 reviews)
"Great location, plenty of space and clean home. "
United States
Brittany T.
$693 nightly
The price is $785
Aug 10 - Aug 11
Total with taxes and fees
Modern West Loop Gem-City Views & Prime Location 5
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)
"Not a bad thing to say about this experience. Host was extremely responsive and helpful, looked exactly like the pictures, had everything we needed, location was perfect and the included parking was such a perk! Highly recommend staying here. I hope to be back! "
United States
Kara B.
$531 nightly
The price is $608
Jul 26 - Jul 27
Total with taxes and fees
River North Rooftop With In and Out Parking 3
Coffee/tea maker, fridge, microwave, oven

River North Private Deck With In and Out Parking

River North Private Deck With In and Out Parking
Downtown Chicago
9.8 out of 10, Exceptional, (12 reviews)
"Excellent location, very clean, spacious."
United States
John David K.
$790 nightly
The price is $922
Jul 23 - Jul 24
Total with taxes and fees
River North Private Deck With In and Out Parking
Interior

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
$519 nightly
The price is $594
Aug 16 - Aug 17
Total with taxes and fees
South Loop Rooftop With In and Out Parking 3
Interior

Modern 3BR Apartment Near North Ave Shops

Modern 3BR Apartment Near North Ave Shops
Near North Side
10.0 out of 10, Exceptional, (1 review)
$527 nightly
The price is $650
Jul 21 - Jul 22
Total with taxes and fees
Modern 3BR Apartment Near North Ave Shops
Interior

Downtown Chicago Stay with Free In & Out Parking 1

Downtown Chicago Stay with Free In & Out Parking 1
Downtown Chicago
9.0 out of 10, Wonderful, (2 reviews)
"My overall experience was great! This 4 bedroom apartment.2 bath with included parking is a great place to stay when you are visiting Chicago and doing activities in the city.The management staff was great to work with. The front desk staff was also great.My family felt safe and we would return.Thigpen Family"
United States
Kimberly T.
$658 nightly
The price is $759
Jul 28 - Jul 29
Total with taxes and fees
Downtown Chicago Stay with Free In & Out Parking 1
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.
$210 nightly
The price is $248
Jul 19 - Jul 20
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.
$233 nightly
The price is $275
Jul 19 - Jul 20
Total with taxes and fees
LIVN Millennium Park Downtown Chicago Prem Studio
1 bedroom, iron/ironing board, travel crib, WiFi

LIVN West Loop Chicago King Studio

LIVN West Loop Chicago King Studio
Downtown Chicago
10.0 out of 10, Exceptional, (4 reviews)
"Amazing studio apartment style room, super clean, very helpful staff, and great location."
United States
William
$237 nightly
The price is $280
Jul 19 - Jul 20
Total with taxes and fees
LIVN West Loop Chicago King Studio
TV, offices

Modern West Loop Gem-City Views & Prime Location 4

Modern West Loop Gem-City Views & Prime Location 4
Downtown Chicago
9.8 out of 10, Exceptional, (11 reviews)
"Amazing accommodation"
United States
Jiri N.
$713 nightly
The price is $810
Aug 9 - Aug 10
Total with taxes and fees
Modern West Loop Gem-City Views & Prime Location 4
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.
$190 nightly
The price is $224
Jul 19 - Jul 20
Total with taxes and fees
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, iron/ironing board, travel crib, WiFi

LIVN West Loop Chicago Queen Superior Studio

LIVN West Loop Chicago Queen Superior Studio
Downtown Chicago
9.0 out of 10, Wonderful, (12 reviews)
"Beautiful place exciting city everything was wonderful"
United States
Kyna C.
$208 nightly
The price is $246
Jul 19 - Jul 20
Total with taxes and fees
LIVN West Loop Chicago Queen Superior Studio
TV, offices

Modern West Loop Gem-City Views & Prime Location 6

Modern West Loop Gem-City Views & Prime Location 6
Downtown Chicago
10.0 out of 10, Exceptional, (26 reviews)
"Great location. "
United States
Tom S.
$862 nightly
The price is $994
Aug 2 - Aug 3
Total with taxes and fees
Modern West Loop Gem-City Views & Prime Location 6
TV, offices

LIVN Millennium Park Downtown Chicago Superior 2 BR

LIVN Millennium Park Downtown Chicago Superior 2 BR
Downtown Chicago
9.2 out of 10, Wonderful, (5 reviews)
$376 nightly
The price is $444
Jul 19 - Jul 20
Total with taxes and fees
LIVN Millennium Park Downtown Chicago Superior 2 BR
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
$454 nightly
The price is $536
Jul 19 - Jul 20
Total with taxes and fees
LIVN Millennium Park Downtown Chicago 2BR
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 Hotel Reviews

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

10/10 Excellent
"Outstanding breakfast and one of the nicer traveling experiences I've had in a while. Big Europe vibes (but with AC!) Highly recommend!"
Nicholas 4-night trip
Posted 5 hours ago
Hotel Riu Plaza Chicago

Price trends for vacation rentals in Chicago

Less expensive
More expensive
Next month
May
July
$396
Month
Price
January
$297
February
$251
March
$291
April
$251
May
$249
June
$400
July
$444
August
$396
September
$367
October
$323
November
$318
December
$347
Price trend information excludes taxes and fees and is based on base rates for a nightly stay for 2 adults found in the last 7 days on our site and averaged for commonly viewed vacation rentals in Chicago. Select dates and complete search for nightly totals inclusive of taxes and fees.

Find out more about Chicago

Everything you need to know about 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 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 Chicago vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chicago vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in 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 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 $197 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 Chicago rentals

At Expedia, we put the best 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 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 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 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.

Explore a world of travel with Expedia

Frequently asked questions

Can I find vacation rentals in Chicago?

Yes, we give you a choice of vacation rentals in Chicago near Six Flags Great America, or you can choose a more secluded option if you want a relaxing stay. Tourists who visit Chicago like the notable monuments and acclaimed art scene. The array of shops and fascinating museums are some other things you might want to check out while you're here.

What are some of the best vacation rentals in Chicago?

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line: This highly rated vacation home rental in Chicago is located in the city center and has a balcony, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Other favorite homes for rent in Chicago are ENVITAE Hotel, 4BR Luxury Modern Apartments and Comfy 4 bedroom Apartment in the center of CHICAGO! 15 mins from Downtown!.

How many vacation rentals are there in Chicago?

With 920 Expedia vacation rentals, you're sure to find just the right place for your Chicago stay.

What can I see and do in Chicago?

Cultural attractions include CIBC Theatre and Symphony Center, whereas Millennium Park and Grant Park are a couple of picturesque spots to enjoy the outdoors. You can also visit some other popular places in town, such as Wrigley Field and Michigan Avenue.

What are vacation rentals like in Chicago?

Vacation rentals are private properties you can stay in for a short or long stay in Chicago. Vacation rentals provide amenities like WiFi and washers and dryers so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, vacation rentals can provide a sense of security away from public hotel elevators and busy front desks while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great option for a family trip or a small group gathering.