A river with a yellow boat, surrounded by tall buildings and a bridge.

Chicago Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Chicago vacation rentals

A modern building with the name 'SENIORAL' prominently displayed on the facade.

1. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,372 reviews)
"Perfect location to stay at if attending the bears games !"
United States
Jacob
$143 nightly
The price is $168
Nov 9 - Nov 10
Total with taxes and fees
Sentral Michigan Avenue
Lake

2. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (68 reviews)
"First time staying there and we absolutely loved our stay. We will definitely be going back."
United States
Iliana
$229 nightly
The price is $263
Nov 1 - Nov 2
Total with taxes and fees
Kasa Lake Shore Chicago
A modern kitchen with a large island, bar stools, and a city view.

3. Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (541 reviews)
"Great location, very clean, loved the gym and cafe!"
United States
Kerry
$324 nightly
The price is $380
Nov 1 - Nov 2
Total with taxes and fees
Level Chicago – Old Town
A modern living room with a dining area, a large window, a flat-screen TV, and a piece of abstract art on the wall.

4. LIVN Millennium Park Downtown Chicago 2BR

LIVN Millennium Park Downtown Chicago 2BR
Downtown Chicago
10.0 out of 10, Exceptional, (13 reviews)
"Excellent location... Very cleaned....it is perfect"
United States
Granada
$419 nightly
The price is $495
Oct 21 - Oct 22
Total with taxes and fees
LIVN Millennium Park Downtown Chicago 2BR
A waiting area with two white chairs, a white table, a television mounted on the wall, and an exit door.

5. Downtown Chicago Stay with Free In & Out Parking 3

Downtown Chicago Stay with Free In & Out Parking 3
Downtown Chicago
10.0 out of 10, Exceptional, (13 reviews)
"Best location"
United States
Eric Dallas
$426 nightly
The price is $479
Nov 9 - Nov 10
Total with taxes and fees
Downtown Chicago Stay with Free In & Out Parking 3
A modern room with a sofa, a dining table, and a window with a view of buildings.

6. LIVN West Loop Chicago 2 BR City View

LIVN West Loop Chicago 2 BR City View
Downtown Chicago
9.4 out of 10, Exceptional, (15 reviews)
"Great property"
United States
duane
$426 nightly
The price is $503
Oct 18 - Oct 19
Total with taxes and fees
LIVN West Loop Chicago 2 BR City View
A modern living room with a fireplace, a flat-screen TV, a sofa, and a dining area.

7. Chic Urban Retreat Near Wrigley Field w/Parking

Chic Urban Retreat Near Wrigley Field w/Parking
Lakeview
10.0 out of 10, Exceptional, (71 reviews)
"Hosts were great, location is great, and it was a great stay."
United States
Ryan G.
$205 nightly
The price is $211
Nov 2 - Nov 3
Total with taxes and fees
Chic Urban Retreat Near Wrigley Field w/Parking
A compact laundry room with a front-loading washer and dryer, a framed picture on the wall, and a towel rack.

8. Plymouth Collection: 3BD 2BA High Floor with Gym

Plymouth Collection: 3BD 2BA High Floor with Gym
Downtown Chicago
9.6 out of 10, Exceptional, (5 reviews)
"The suite was excellent. Clean and very well furnished. The building is located within walking distance to many of the things that we did. We would stay in this place again in a heartbeat. Very pleased with our experience"
United States
Derek M.
$813 nightly
The price is $950
Nov 14 - Nov 15
Total with taxes and fees
Plymouth Collection: 3BD 2BA High Floor with Gym
A gym with weightlifting equipment, benches, and a mirrored wall.

9. South Loop Rooftop With In & Out Parking 1

South Loop Rooftop With In & Out Parking 1
Downtown Chicago
9.6 out of 10, Exceptional, (4 reviews)
"Perfect location for our first trip to Chicago with our 1-year-old. Very close to a 7-11 and CVS for forgotten essentials, but most of all the parks and museums. Check-in and check-out were very easy. I recommend unloading your vehicle before parking as it is not attached to the parking garage."
United States
Shayla S.
$453 nightly
The price is $512
Nov 5 - Nov 6
Total with taxes and fees
South Loop Rooftop With In & Out Parking 1
A modern kitchen with a marble island, wooden cabinets, and a dining area with a table and chairs.

10. River North Rooftop With In and Out Parking 3

River North Rooftop With In and Out Parking 3
Downtown Chicago
9.0 out of 10, Wonderful, (10 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.
$412 nightly
The price is $462
Nov 3 - Nov 4
Total with taxes and fees
River North Rooftop With In and Out Parking 3
A neatly made bed with white bedding, two bedside tables with lamps, and a single decorative pillow.

11. Wabash 4BR - Pool, Free In & Out Parking 2

Wabash 4BR - Pool, Free In & Out Parking 2
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"Espectacular!!! La ubicación y el departamento es excelente. Pasamos unos días increibles."
Spain
Diana Sofia B.
$795 nightly
The price is $911
Oct 22 - Oct 23
Total with taxes and fees
Wabash 4BR - Pool, Free In & Out Parking 2
A room with a skylight, a mounted TV, and a door.

12. Luxury River North Loft | Walk to Mag Mile, Riverwalk & Top Restaurants

Luxury River North Loft | Walk to Mag Mile, Riverwalk & Top Restaurants
Downtown Chicago
$401 nightly
The price is $492
Nov 9 - Nov 10
Total with taxes and fees
Luxury River North Loft | Walk to Mag Mile, Riverwalk & Top Restaurants
A hotel room with a bed, two bedside lamps, a wall-mounted artwork, and a small table with a lamp.

13. 2BR Apt with 2 Baths & Laundry

2BR Apt with 2 Baths & Laundry
Near West Side
10.0 out of 10, Exceptional, (1 review)
"The property was very clean and perfect for our overnight stay. Thank you"
United States
michele
$227 nightly
The price is $252
Nov 2 - Nov 3
Total with taxes and fees
2BR Apt with 2 Baths & Laundry
A modern kitchen with white cabinets, a central island with stools, a microwave, and a refrigerator.

14. 3BR Complete and Spacious Apartment in Ideal Spot

3BR Complete and Spacious Apartment in Ideal Spot
West Town
8.4 out of 10, Very good, (23 reviews)
"My wife and I stayed here when we came to town for a concert at the united center. We actually walked to the venue and it was about 45 mins, a lovely walk. It was a very convenient location, lovely apartment, and the host communicated very well. Check in and out was easy. Great neighborhood. Would definitely stay here again."
United States
Francis
$228 nightly
The price is $252
Oct 20 - Oct 21
Total with taxes and fees
3BR Complete and Spacious Apartment in Ideal Spot
A rooftop terrace with a fire pit, seating area, and a city skyline view.

15. Penthouse and Private Rooftop with Skyline Views, Grill, and Fire Pit - Sleeps 6

Penthouse and Private Rooftop with Skyline Views, Grill, and Fire Pit - Sleeps 6
West Town
10.0 out of 10, Exceptional, (4 reviews)
"Excellent - highly recommended."
United States
Jay J.
$205 nightly
The price is $238
Nov 4 - Nov 5
Total with taxes and fees
Penthouse and Private Rooftop with Skyline Views, Grill, and Fire Pit - Sleeps 6
A bedroom with a bed, bedside tables, a ceiling fan, framed pictures, and a window.

16. Stylish Gold Coast 1BR with Vintage Flair

Stylish Gold Coast 1BR with Vintage Flair
Downtown Chicago
$317 nightly
The price is $353
Nov 9 - Nov 10
Total with taxes and fees
Stylish Gold Coast 1BR with Vintage Flair
A modern living room with large windows, a flat-screen TV, a sofa, a coffee table, and a dining area with stools and a small table.

17. 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, (28 reviews)
"Great location. "
United States
Tom S.
$859 nightly
The price is $990
Oct 28 - Oct 29
Total with taxes and fees
Modern West Loop Gem-City Views & Prime Location 6
A modern bedroom with a bed, a sofa, and a hanging plant.

18. Cozy studio in Andersonville Chicago

Cozy studio in Andersonville Chicago
Edgewater
9.6 out of 10, Exceptional, (102 reviews)
"Great location for us near the Edgewood neighborhood. Property was very clean, bed comfy, and owner responsive. We’d stay here again!"
United States
Sherry M.
$113 nightly
The price is $139
Nov 2 - Nov 3
Total with taxes and fees
Cozy studio in Andersonville Chicago
A living room with a large arched window, a fireplace, and a sofa with patterned cushions.

19. Wrigley Field Legend Suite 4 Bedrooms, 2 Bathrooms

Wrigley Field Legend Suite 4 Bedrooms, 2 Bathrooms
Lakeview
9.6 out of 10, Exceptional, (33 reviews)
"This place was perfect for our quick weekend getaway!"
United States
Kate P.
$887 nightly
The price is $1,095
Oct 18 - Oct 19
Total with taxes and fees
Wrigley Field Legend Suite 4 Bedrooms, 2 Bathrooms
A bedroom with a large bed, a bedside table, a nightstand, a window with blinds, and a wall-mounted artwork.

20. Comfortable 3BR/2BA Haven | Ideal for Families

Comfortable 3BR/2BA Haven | Ideal for Families
Avondale
9.4 out of 10, Exceptional, (15 reviews)
"Great neighborhood - excellent communication - large space for family."
United States
Marc
$227 nightly
The price is $250
Oct 18 - Oct 19
Total with taxes and fees
Comfortable 3BR/2BA Haven | Ideal for Families
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

Freehand Chicago

Freehand Chicago

10/10 Excellent
"It was comfortable"
Ece 4-night trip
Posted 2 hours ago
Freehand Chicago

Price trends for vacation rentals in Chicago

Less expensive
More expensive
Next month
May
July
$318
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 $81 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 theater 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 Sleeps 18 • 8BR • Game Room • Gym • Theater and LUXE 3 BR, 2 BA + Hot Tub.

How many vacation rentals are there in Chicago?

With 933 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 Soldier Field and Navy Pier.

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.