Chicago Vacation Rentals

Check prices for these dates

In two weeks
Jun 19 - Jun 21
In two months
Jul 31 - Aug 2
In three months
Aug 28 - Aug 30
In four months
Sep 25 - Sep 27

Our top choices for Chicago vacation rentals

Desk, iron/ironing board, travel crib, WiFi

Chic Studio in the Heart of the Gold Coast

Chic Studio in the Heart of the Gold Coast
Downtown Chicago
10.0 out of 10, Exceptional, (6 reviews)
"This was a great stay! Great size and location. Would recommend it a lot."
United States
Dulce
$186 nightly
The price is $209
Jun 8 - Jun 9
Total with taxes and fees
Chic Studio in the Heart of the Gold Coast
1 bedroom, iron/ironing board, travel crib, WiFi

West Loop Living – Bright 1BR

West Loop Living – Bright 1BR
Downtown Chicago
10.0 out of 10, Exceptional, (11 reviews)
"Great spot next to the green line train a few restaurants and a Starbucks right up the street I will book again for sure "
United States
2k G.
$285 nightly
The price is $324
Jun 4 - Jun 5
Total with taxes and fees
West Loop Living – Bright 1BR
Indoor pool

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,178 reviews)
"Great location"
United States
Karen
$225 nightly
The price is $264
Jul 2 - Jul 3
Total with taxes and fees
Sentral Michigan Avenue
TV, offices

Chicago-Themed 1BR in a Central Spot near Downtown

Chicago-Themed 1BR in a Central Spot near Downtown
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"Clean spacious great location easy to get everywhere "
United States
Melissa M.
$243 nightly
The price is $274
Jun 8 - Jun 9
Total with taxes and fees
Chicago-Themed 1BR in a Central Spot near Downtown
TV, offices

Sunlit 1BR Apartment | Warm & Welcoming Space

Sunlit 1BR Apartment | Warm & Welcoming Space
Downtown Chicago
10.0 out of 10, Exceptional, (2 reviews)
"Host was very friendly and informative. Place was clean and close to lots of fun. Trains loud and busy but knew that going in. "
United States
Tyler B.
$234 nightly
The price is $264
Jun 3 - Jun 4
Total with taxes and fees
Sunlit 1BR Apartment | Warm & Welcoming Space
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, (23 reviews)
"Everything was walking distance and had everything needed for a comfortable stay "
United States
Daniel
$661 nightly
The price is $745
Jun 7 - Jun 8
Total with taxes and fees
Modern West Loop Gem-City Views & Prime Location 6
Fridge, microwave, oven, stovetop

River North Rooftop With In and Out Parking 5

River North Rooftop With In and Out Parking 5
Downtown Chicago
9.6 out of 10, Exceptional, (4 reviews)
"Everything was amazing, property was even better than expected"
United States
Jacob
$438 nightly
The price is $505
Jun 10 - Jun 11
Total with taxes and fees
River North Rooftop With In and Out Parking 5
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, (484 reviews)
"Staff was amazing and the apartment building was phenomenally clean!"
United States
Seke
$292 nightly
The price is $343
Jun 30 - Jul 1
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
10.0 out of 10, Exceptional, (11 reviews)
$885 nightly
The price is $1,092
Jun 25 - Jun 26
Total with taxes and fees
ENVITAE Hotel, 4BR Luxury Modern Apartments
Interior

River North Rooftop With In and Out Parking 3

River North Rooftop With In and Out Parking 3
Downtown Chicago
9.6 out of 10, Exceptional, (5 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.
$518 nightly
The price is $592
Jun 23 - Jun 24
Total with taxes and fees
River North Rooftop With In and Out Parking 3
1 bedroom, WiFi, bed sheets

1BR Modern Luxe Apt with In-Unit Laundry

1BR Modern Luxe Apt with In-Unit Laundry
Downtown Chicago
8.8 out of 10, Excellent, (3 reviews)
"Great experience for me and my wife I would definitely come back "
United States
ShowtimeFam1
$263 nightly
The price is $298
Jun 10 - Jun 11
Total with taxes and fees
1BR Modern Luxe Apt with In-Unit Laundry
TV, offices

LIVN Millennium Park Downtown Chicago Superior 1BR

LIVN Millennium Park Downtown Chicago Superior 1BR
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"Cute little place with all the necessities - old city feel with mlodern conveniences"
United States
Mary D.
$386 nightly
The price is $456
Jun 8 - Jun 9
Total with taxes and fees
LIVN Millennium Park Downtown Chicago Superior 1BR
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, (2 reviews)
"Excellent stay. Great area and very happy with everything"
United States
Abigail B.
$291 nightly
The price is $344
Jun 8 - Jun 9
Total with taxes and fees
LIVN West Loop Chicago Classic Queen Studio
Exterior

Spacious 4BR Central Apartment w/ Skyline Views

Spacious 4BR Central Apartment w/ Skyline Views
Near North Side
10.0 out of 10, Exceptional, (17 reviews)
"Great location, comfortable room, welcoming host."
United States
Treseanne A.
$860 nightly
The price is $1,061
Jun 18 - Jun 19
Total with taxes and fees
Spacious 4BR Central Apartment w/ Skyline Views
TV, offices

Downtown Chicago Stay with Free In & Out Parking 5

Downtown Chicago Stay with Free In & Out Parking 5
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"This VRBO was perfect for our family as we visited our college student in downtown Chicago. Plenty of space, sparkling clean, comfy beds. Only two things that I think could be improved/better communicated: only one key card is provided, and the beds are full size not queen (but they were SUPER comfortable!!!)"
United States
Gina C.
$713 nightly
The price is $833
Jun 25 - Jun 26
Total with taxes and fees
Downtown Chicago Stay with Free In & Out Parking 5
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.
$1,166 nightly
The price is $1,439
Jun 26 - Jun 27
Total with taxes and fees
Premium Urban 4BR - Perfect Mix of Comfort & Location
TV, offices

3BR Luxury Suite w/Gym and Balcony

3BR Luxury Suite w/Gym and Balcony
Downtown Chicago
9.4 out of 10, Exceptional, (28 reviews)
"The apartment is in a good location, close to restaurants and bars. There is a nice park not far away and we had a lovely stay. "
United States
shayna j.
$1,313 nightly
The price is $1,620
Jun 26 - Jun 27
Total with taxes and fees
3BR Luxury Suite w/Gym and Balcony
TV, offices

Modern West Loop Gem-City Views & Prime Location 5

Modern West Loop Gem-City Views & Prime Location 5
Downtown Chicago
9.4 out of 10, Exceptional, (3 reviews)
"Great location, plenty of space and clean home. "
United States
Brittany T.
$696 nightly
The price is $789
Jun 28 - Jun 29
Total with taxes and fees
Modern West Loop Gem-City Views & Prime Location 5
Interior

Modern West Loop Gem-City Views & Prime Location 3

Modern West Loop Gem-City Views & Prime Location 3
Downtown Chicago
10.0 out of 10, Exceptional, (7 reviews)
"Loved the place 4 bedroom & 4 bathrooms was ideal for our stayGreat locationLoved the well stocked convenience store a block away "
United States
Tina Y.
$642 nightly
The price is $722
Jun 21 - Jun 22
Total with taxes and fees
Modern West Loop Gem-City Views & Prime Location 3
TV, offices

River North Rooftop With In and Out Parking 1

River North Rooftop With In and Out Parking 1
Downtown Chicago
9.8 out of 10, Exceptional, (6 reviews)
"Awesome location, great place would definitely recommend will hopefully return"
United States
lucas c.
$492 nightly
The price is $572
Jun 10 - Jun 11
Total with taxes and fees
River North Rooftop With In and Out Parking 1
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
"Fantastic stay. The location is perfect. The breakfast was superb and the roodtop bar fantastic"
Geraint 6-night trip
Posted 2 hours ago
Hotel Riu Plaza Chicago

Price trends for vacation rentals in Chicago

Less expensive
More expensive
This month
Next month
April
July
$407
$446
Month
Price
January
$340
February
$242
March
$233
April
$230
May
$249
June
$407
July
$446
August
$419
September
$376
October
$344
November
$329
December
$403
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 $162 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 entertainment choices. 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?

ENVITAE Hotel, 4BR Luxury Modern Apartments: This highly rated vacation home rental in Chicago is located in the city center and offers a barbecue grill, air-conditioning, and laundry facilities to help you feel perfectly comfortable 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 Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed and Clean, Private, Cozy Urban Oasis Chicago Greystone In Heart of Logan Square.

How many vacation rentals are there in Chicago?

With 935 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.