Chicago Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

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, (1,401 reviews)
"10/10 2nd time staying here!"
United States
Rosa
$135 nightly
The price is $159
Nov 22 - Nov 23
Total with taxes and fees
Sentral Michigan Avenue
Lake

2. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (83 reviews)
"The bathroom was really clean. The beds were really comfortable"
United States
Jair
$211 nightly
The price is $251
Nov 22 - Nov 23
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, (557 reviews)
"Super clean and friendly staff! Would definitely stay here again"
United States
Robert Edward
$236 nightly
The price is $277
Nov 23 - Nov 24
Total with taxes and fees
Level Chicago – Old Town
A modern living room with a fireplace, a dining area with a wooden table and chairs, and a kitchen with a white railing.

4. Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
9.4 out of 10, Exceptional, (49 reviews)
"Clean room"
United States
Michael
$121 nightly
The price is $143
Nov 5 - Nov 6
Total with taxes and fees
Wrigleyville Suites
A modern living room with a dining area, a large window, a flat-screen TV, and a piece of abstract art on the wall.

5. LIVN Millennium Park Downtown Chicago 2BR

LIVN Millennium Park Downtown Chicago 2BR
Downtown Chicago
10.0 out of 10, Exceptional, (16 reviews)
"Thanks! Very easy check in and very clean property with more than adequate amenities."
United States
tarek m.
$214 nightly
The price is $252
Nov 8 - Nov 9
Total with taxes and fees
LIVN Millennium Park Downtown Chicago 2BR
A modern living room with a fireplace, a flat-screen TV, a sofa, and a dining area.

6. Chic Urban Retreat Near Wrigley Field w/Parking

Chic Urban Retreat Near Wrigley Field w/Parking
Lakeview
10.0 out of 10, Exceptional, (72 reviews)
"We had a very nice stay, the place was comfortable and clean, beautifully decorated. We only wish we would’ve had more time! And bonus it came with a parking spot. We hope to come back again!"
United States
Rachael
$204 nightly
The price is $210
Nov 11 - Nov 12
Total with taxes and fees
Chic Urban Retreat Near Wrigley Field w/Parking
A hotel room with a large bed, a window with a view of buildings, a nightstand with a lamp, and two framed pictures on the wall.

7. LIVN West Loop Chicago Queen Superior Studio

LIVN West Loop Chicago Queen Superior Studio
Downtown Chicago
9.6 out of 10, Exceptional, (29 reviews)
"Clean, comfortable, effortless check-in and checkout process, and in a very convenient location. Would stay again!"
United States
Tara H.
$161 nightly
The price is $189
Nov 9 - Nov 10
Total with taxes and fees
LIVN West Loop Chicago Queen Superior Studio
A wooden dining table with two chairs, a potted plant, and a painting on the wall.

8. 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, (1 review)
"Great little spot in a fun area of downtown Chicago. Lots of bars & restaurants within walking distance."
United States
Ryan
$222 nightly
The price is $242
Nov 16 - Nov 17
Total with taxes and fees
Chic Studio in the Heart of the Gold Coast
A modern living room with a flat-screen TV, a sofa, a coffee table, and a dining area with a bar stool.

9. 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, (24 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
$194 nightly
The price is $211
Nov 9 - Nov 10
Total with taxes and fees
3BR Complete and Spacious Apartment in Ideal Spot
Room

10. Downtown Chicago Stay with Free In & Out Parking-2

Downtown Chicago Stay with Free In & Out Parking-2
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"Amazing space designed with travelers in mind. Bring ear plugs if you're sleeping sensitive to city sounds. Downtown city views and walking distance cannot be beat."
United States
Rachel M.
$641 nightly
The price is $738
Nov 26 - Nov 27
Total with taxes and fees
Downtown Chicago Stay with Free In & Out Parking-2
A modern kitchen with a large island, a built-in refrigerator, and a view of the city through large windows.

11. 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.
$321 nightly
The price is $361
Nov 18 - Nov 19
Total with taxes and fees
River North Private Balcony With In and Out Parking
A modern balcony with wicker furniture, a glass table, and a city skyline view.

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

Wabash 4BR - Pool, Free In & Out Parking 4
Downtown Chicago
10.0 out of 10, Exceptional, (2 reviews)
"Nice place to stay."
United States
William H.
$550 nightly
The price is $608
Nov 11 - Nov 12
Total with taxes and fees
Wabash 4BR - Pool, Free In & Out Parking 4
A modern living room with a spiral staircase, a green sofa, a round coffee table, and a large abstract painting on the wall.

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

Luxury River North Loft | Walk to Mag Mile, Riverwalk & Top Restaurants
Downtown Chicago
$362 nightly
The price is $444
Nov 16 - Nov 17
Total with taxes and fees
Luxury River North Loft | Walk to Mag Mile, Riverwalk & Top Restaurants
A modern kitchen with wooden cabinets, a stainless steel dishwasher, a microwave, a coffee maker, and a toaster.

14. Smart Simple and Spacious 4BR Apt

Smart Simple and Spacious 4BR Apt
South Loop
8.4 out of 10, Very good, (14 reviews)
"Everything was exactly as described."
United States
Sydney D.
$352 nightly
The price is $380
Nov 12 - Nov 13
Total with taxes and fees
Smart Simple and Spacious 4BR Apt
A bedroom with a bed, a desk, a chair, a TV, and a window with blinds.

15. Flexhome Wicker Park • Stylish 2BR • Sleeps 6

Flexhome Wicker Park • Stylish 2BR • Sleeps 6
West Town
10.0 out of 10, Exceptional, (3 reviews)
"Wouldn’t change a thing. Great location to downtown and all the things that we wanted to do."
United States
beth m.
$177 nightly
The price is $218
Nov 26 - Nov 27
Total with taxes and fees
Flexhome Wicker Park • Stylish 2BR • Sleeps 6
A modern apartment with a living area, kitchen, and large windows offering city views.

16. 3BR Luxury Suite w/Gym and Balcony

3BR Luxury Suite w/Gym and Balcony
Downtown Chicago
9.6 out of 10, Exceptional, (38 reviews)
"The property was great. Perfect location, beautiful, good decor. Definitely recommend it and stay again there. Host was very good too, very responsive when I needed it."
United States
Adrian
$655 nightly
The price is $808
Nov 22 - Nov 23
Total with taxes and fees
3BR Luxury Suite w/Gym and Balcony
A modern living room with a sectional sofa, a dining table with chairs, and large windows offering city views.

17. Modern West Loop Gem-City Views & Prime Location 4

Modern West Loop Gem-City Views & Prime Location 4
Downtown Chicago
9.4 out of 10, Exceptional, (15 reviews)
"Amazing accommodation"
United States
Jiri N.
$577 nightly
The price is $642
Nov 19 - Nov 20
Total with taxes and fees
Modern West Loop Gem-City Views & Prime Location 4
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, (110 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.
$110 nightly
The price is $135
Nov 30 - Dec 1
Total with taxes and fees
Cozy studio in Andersonville Chicago
Interior

19. Premium Urban 4BR - Perfect Mix of Comfort & Location

Premium Urban 4BR - Perfect Mix of Comfort & Location
Near North Side
9.6 out of 10, Exceptional, (10 reviews)
"Great location with large beds which made it amazing for our group. Easy access to public transport and a cute neighborhood"
United States
Kortnee
$373 nightly
The price is $460
Nov 18 - Nov 19
Total with taxes and fees
Premium Urban 4BR - Perfect Mix of Comfort & Location
A hotel room with a large bed, two bedside tables, two lamps, and two abstract paintings on the wall.

20. Modern 1BR in Prime West Loop Location

Modern 1BR in Prime West Loop Location
Downtown Chicago
8.0 out of 10, Very good, (1 review)
"Everything was great, good location, all went smooth.It is right by the L train so is a bit noisy. Host left earplugs which was nice."
United States
Doris L.
$253 nightly
The price is $276
Nov 9 - Nov 10
Total with taxes and fees
Modern 1BR in Prime West Loop Location
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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Find vacation rentals that suit your style

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Top Chicago Hotel Reviews

A person relaxing on a sofa with a window view of a building, a table with a glass of wine, and a vase with flowers.
L7 Chicago by LOTTE

L7 Chicago by LOTTE

L7 Chicago by LOTTE
Downtown Chicago

10/10 Excellent

I stayed here to visit my child that attends the Art Institute and I was completely impressed. I will definitely stay here again.
United States
Erin
Reviewed October 20, 2024
L7 Chicago by LOTTE

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 $135 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.

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.

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