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 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Chicago vacation rentals

Exterior

1. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,327 reviews)
"clean property, amazing staff, in-unit laundry machines, awesome location"
United States
Allison
$177 nightly
The price is $208
Sep 27 - Sep 28
Total with taxes and fees
Sentral Michigan Avenue
Lake

2. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
8.4 out of 10, Very good, (35 reviews)
"Location is perfect to visit Chicago for the weekend. The unit is clean and size is perfect for the family."
United States
Xiaoyu
$919 nightly
The price is $1,093
Oct 1 - Oct 2
Total with taxes and fees
Kasa Lake Shore Chicago
Full-size fridge, microwave, oven, stovetop

3. Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (527 reviews)
"Location and facility was very nice"
United States
Brian
$358 nightly
The price is $420
Sep 28 - Sep 29
Total with taxes and fees
Level Chicago – Old Town
TV, offices

4. LIVN West Loop Chicago 2 BR City View

LIVN West Loop Chicago 2 BR City View
Downtown Chicago
9.4 out of 10, Exceptional, (12 reviews)
"Great property"
United States
duane
$244 nightly
The price is $288
Sep 27 - Sep 28
Total with taxes and fees
LIVN West Loop Chicago 2 BR City View
TV, offices

5. LIVN Millennium Park Downtown Chicago 2BR

LIVN Millennium Park Downtown Chicago 2BR
Downtown Chicago
10.0 out of 10, Exceptional, (12 reviews)
"Excellent location... Very cleaned....it is perfect"
United States
Granada
$239 nightly
The price is $282
Sep 27 - Sep 28
Total with taxes and fees
LIVN Millennium Park Downtown Chicago 2BR
TV, offices

6. 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, (12 reviews)
"Perfect place for my family’s visit to Chicago."
United States
Jason L.
$528 nightly
The price is $605
Sep 27 - Sep 28
Total with taxes and fees
Downtown Chicago Stay with Free In & Out Parking 3
Coffee/tea maker, fridge, microwave, oven

7. River North Rooftop With In and Out Parking 5

River North Rooftop With In and Out Parking 5
Downtown Chicago
9.8 out of 10, Exceptional, (7 reviews)
"Everything was amazing"
United States
Kimberly R.
$485 nightly
The price is $563
Oct 4 - Oct 5
Total with taxes and fees
River North Rooftop With In and Out Parking 5
Interior

8. 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
$406 nightly
The price is $454
Oct 14 - Oct 15
Total with taxes and fees
South Loop Rooftop With In and Out Parking 3
Living area

9. Wrigley Field Stadium Suite 4 Bedroom 2 Bathroom

Wrigley Field Stadium Suite 4 Bedroom 2 Bathroom
Lakeview
9.8 out of 10, Exceptional, (28 reviews)
"Location cannot be beat! So close to Wrigley and so fun! "
United States
Celia A
$879 nightly
The price is $1,085
Sep 21 - Sep 22
Total with taxes and fees
Wrigley Field Stadium Suite 4 Bedroom 2 Bathroom
TV, offices

10. River North Private Balcony With In and Out Parking

River North Private Balcony With In and Out Parking
Downtown Chicago
10.0 out of 10, Exceptional, (6 reviews)
"Place was easily accessible- very clean and an amazing alternative to hotel living for 2 colleagues. Coffee was available and all the basics of a hotel. "
United States
Rae M.
$418 nightly
The price is $481
Sep 29 - Sep 30
Total with taxes and fees
River North Private Balcony With In and Out Parking
Beach nearby

11. Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24

Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24
Lincoln Park
9.8 out of 10, Exceptional, (192 reviews)
"Awesome house for family events. Great neighborhood and gathering space was great"
United States
Ann V.
$763 nightly
The price is $941
Oct 5 - Oct 6
Total with taxes and fees
Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24
Interior

12. Lincoln Park Cozy 3bd Home near Zoo | Lake | Shops

Lincoln Park Cozy 3bd Home near Zoo | Lake | Shops
Lincoln Park
9.6 out of 10, Exceptional, (43 reviews)
"We had a really nice stay at the Village Inn. We appreciated that artistic furnishings and decorations, and the thoughtful touches throughout. (We are a white noise family, so we were very happy to find a white noise machine in every bedroom!)The neighborhood is very quiet and also close to great shops and restaurants as well as the train. We enjoyed being able to walk to dinner in the evening, and walk to the train to take a short ride right to the Art Institute. The kitchen was great for...
United States
Andrea M.
$451 nightly
The price is $557
Sep 22 - Sep 23
Total with taxes and fees
Lincoln Park Cozy 3bd Home near Zoo | Lake | Shops
2 bedrooms, iron/ironing board, travel crib, WiFi (free)

13. Zen City Escape | Patio + Free Parking

Zen City Escape | Patio + Free Parking
West Town
10.0 out of 10, Exceptional, (4 reviews)
"I had an amazing stay at Tracee's place. It was quiet, clean, plenty of parking and served all of my needs. Tracee was responsive and very accommodating of my stay."
United States
Denise R.
$387 nightly
The price is $446
Sep 22 - Sep 23
Total with taxes and fees
Zen City Escape | Patio + Free Parking
Outdoor dining

14. 2R- ❤️ Stylish and Cozy 2BR in Logan Square!

2R- ❤️ Stylish and Cozy 2BR in Logan Square!
Logan Square
10.0 out of 10, Exceptional, (58 reviews)
"Excellent stay. Nice location"
United States
Daniel R.
$292 nightly
The price is $345
Sep 28 - Sep 29
Total with taxes and fees
2R- ❤️ Stylish and Cozy 2BR in Logan Square!
Property grounds

15. Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley

Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley
North Center
9.8 out of 10, Exceptional, (102 reviews)
"We really enjoyed the space, and it was perfect for us."
United States
Nate T.
$260 nightly
The price is $321
Sep 21 - Sep 22
Total with taxes and fees
Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley
Fireplace

16. 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.
$879 nightly
The price is $1,085
Sep 21 - Sep 22
Total with taxes and fees
Wrigley Field Legend Suite 4 Bedrooms, 2 Bathrooms
TV

17. 3BR Complete and Spacious Apartment in Ideal Spot

3BR Complete and Spacious Apartment in Ideal Spot
West Town
8.2 out of 10, Very good, (22 reviews)
"absolutely would stay here again. Great property and great communcation"
United States
Daniel J.
$205 nightly
The price is $225
Sep 21 - Sep 22
Total with taxes and fees
3BR Complete and Spacious Apartment in Ideal Spot
Coffee/tea maker, fridge, microwave, oven

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

Wabash 4BR - Pool, Free In & Out Parking 4
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"Nice place to stay."
United States
William H.
$626 nightly
The price is $702
Sep 29 - Sep 30
Total with taxes and fees
Wabash 4BR - Pool, Free In & Out Parking 4
Beach

19. Luxury Lincoln Park Gem with Gourmet Kitchen & City Views

Luxury Lincoln Park Gem with Gourmet Kitchen & City Views
Lincoln Park
10.0 out of 10, Exceptional, (15 reviews)
"Home was well maintained and clean. Location was fantastic with an easy walk to shops and restaurants. "
United States
Nikki R.
$2,265 nightly
The price is $2,626
Oct 5 - Oct 6
Total with taxes and fees
Luxury Lincoln Park Gem with Gourmet Kitchen & City Views
Dining

20. The Dakin Estate: A refined 4BR Art Deco speakeasy duplex in Wrigleyville. Featuring curated interiors, elevated finishes, and a private entertainment lounge just minutes from Wrigley Field, dining, nightlife, and Chicago’s iconic attractions.

The Dakin Estate: A refined 4BR Art Deco speakeasy duplex in Wrigleyville. Featuring curated interiors, elevated finishes, and a private entertainment lounge just minutes from Wrigley Field, dining, nightlife, and Chicago’s iconic attractions.
Lakeview
10.0 out of 10, Exceptional, (4 reviews)
"Great location in Wrigleyville! Comfortable, clean, and very nicely decorated. Will definitely be back!"
United States
Rhonda B.
$826 nightly
The price is $1,007
Sep 21 - Sep 22
Total with taxes and fees
The Dakin Estate: A refined 4BR Art Deco speakeasy duplex in Wrigleyville. Featuring curated interiors, elevated finishes, and a private entertainment lounge just minutes from Wrigley Field, dining, nightlife, and Chicago’s iconic attractions.
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

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

10/10 Excellent
"room was clean, hotel very nice, parking was a bit annoying as they have no parking directly by the hotel or valet but to be expected with downtown chicago. still would 10/10 recommend"
Taijay 2-night trip
Posted 2 hours ago
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

Price trends for vacation rentals in Chicago

Less expensive
More expensive
Next month
May
July
$323
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 $76 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 LUXE 3 BR, 2 BA + Hot Tub and Cozy 3-bedroom house in family-oriented Melrose Park..

How many vacation rentals are there in Chicago?

With 919 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.