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Chicago Holiday Rentals

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Chicago holiday 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, (1,390 reviews)
"10/10 2nd time staying here!"
United States
Rosa
The price is NZ$295
includes taxes & fees
9 Nov - 10 Nov
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, (75 reviews)
"First time staying there and we absolutely loved our stay. We will definitely be going back."
United States
Iliana
The price is NZ$366
includes taxes & fees
4 Nov - 5 Nov
Kasa Lake Shore Chicago
A wooden dining table with two chairs, a potted plant, and a painting on the wall.

3. 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
The price is NZ$450
includes taxes & fees
10 Nov - 11 Nov
Chic Studio in the Heart of the Gold Coast
A room with a round table, two chairs, a vase with flowers, a plate with food, and a window with blinds.

4. LIVN Millennium Park Downtown Chicago Studio

LIVN Millennium Park Downtown Chicago Studio
Downtown Chicago
9.4 out of 10, Exceptional, (12 reviews)
"Great location"
United States
Jason P.
The price is NZ$387
includes taxes & fees
1 Nov - 2 Nov
LIVN Millennium Park Downtown Chicago Studio
A modern living room with a fireplace, a dining area with a wooden table and chairs, and a kitchen with a white railing.

5. Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
9.6 out of 10, Exceptional, (47 reviews)
"What a gem right next to Wrigleyville Stadium! I had an emergency and needed somewhere to stay for two nights while my son was in the hospital. This was the perfect accommodation walkable to where I needed to go. Clean community townhome with lock off rooms, community kitchen and living room room – very lovely environment and excellent location. Walkable to many restaurants."
United States
Diana
The price is NZ$306
includes taxes & fees
27 Oct - 28 Oct
Wrigleyville Suites
A rooftop terrace with a brick wall, large windows, and a metal railing.

6. Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake

Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake
Uptown
9.2 out of 10, Wonderful, (30 reviews)
"Very nice and clean place in a great location if you are going to Wrigley"
United States
Paul J.
The price is NZ$469
includes taxes & fees
4 Nov - 5 Nov
Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake
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, (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
The price is NZ$357
includes taxes & fees
9 Nov - 10 Nov
Chic Urban Retreat Near Wrigley Field w/Parking
A modern kitchen with a large island, bar stools, and a city view.

8. Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (549 reviews)
"Super clean and friendly staff! Would definitely stay here again"
United States
Robert Edward
The price is NZ$535
includes taxes & fees
1 Nov - 2 Nov
Level Chicago – Old Town
A rooftop terrace with a brick wall, large windows, and a metal railing.

9. Artistic Loft Rooftop | 13 mins DT | 4 mins Lake

Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
Uptown
10.0 out of 10, Exceptional, (60 reviews)
"Clean, efficient, and conveniently located to plenty of transportation and culture."
United States
Michael S.
The price is NZ$516
includes taxes & fees
29 Oct - 30 Oct
Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
A modern living room with a flat-screen TV, a sofa, a coffee table, and a dining area with a bar stool.

10. 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
The price is NZ$456
includes taxes & fees
27 Oct - 28 Oct
3BR Complete and Spacious Apartment in Ideal Spot
A desk with a computer monitor, keyboard, mouse, a lamp, a mug, a plant, and a clock.

11. Private Workspace • Sleeps 4 • Modern and Stylish

Private Workspace • Sleeps 4 • Modern and Stylish
Irving Park
10.0 out of 10, Exceptional, (7 reviews)
"The apartment was just as described, modern, comfortable, very clean and perfect for two people for our five night stay. Very comfortable bed and we especially appreciated the easy entry lock. Great location. Good communication with property manager but we had zero complaints. We would stay again!"
United States
Margaret N.
The price is NZ$494
includes taxes & fees
3 Nov - 4 Nov
Private Workspace • Sleeps 4 • Modern and Stylish
A modern living room with a spiral staircase, a green sofa, a round coffee table, and a large abstract painting on the wall.

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
The price is NZ$1,300
includes taxes & fees
8 Nov - 9 Nov
Luxury River North Loft | Walk to Mag Mile, Riverwalk & Top Restaurants
A narrow hallway with a concrete wall, a wooden floor, a small table, and a large mirror on the right.

13. South Loop Rooftop With In and Out Parking 2

South Loop Rooftop With In and Out Parking 2
Downtown Chicago
10.0 out of 10, Exceptional, (2 reviews)
"Great place to stay! Parking was easy and secure. The building was super clean and had lots of amenities. Host was very responsive to messages and very accommodating to our last minute schedule changes. "
United States
Kara V.
South Loop Rooftop With In and Out Parking 2
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.

14. LIVN West Loop Chicago Queen Superior Studio

LIVN West Loop Chicago Queen Superior Studio
Downtown Chicago
9.6 out of 10, Exceptional, (27 reviews)
"Clean, comfortable, effortless check-in and checkout process, and in a very convenient location. Would stay again!"
United States
Tara H.
The price is NZ$447
includes taxes & fees
1 Nov - 2 Nov
LIVN West Loop Chicago Queen Superior Studio
A hallway with wooden flooring, white walls, and a door.

15. Flexhome West Town · Spacious 2BR Duplex · Sleeps 8

Flexhome West Town · Spacious 2BR Duplex · Sleeps 8
West Town
10.0 out of 10, Exceptional, (3 reviews)
"Thank you. We had a wonderful stay."
United States
Janice G.
The price is NZ$333
includes taxes & fees
10 Nov - 11 Nov
Flexhome West Town · Spacious 2BR Duplex · Sleeps 8
A hotel room with a large bed, a desk, a chair, a lamp, and artwork on the wall.

16. Flexhome Ukrainian Village • 2BR • Walkable + Private Balcony · Sleeps 6

Flexhome Ukrainian Village • 2BR • Walkable + Private Balcony · Sleeps 6
West Town
9.0 out of 10, Wonderful, (16 reviews)
"Great location! Comfortable and quiet. "
United States
Jonalyn B.
The price is NZ$326
includes taxes & fees
29 Oct - 30 Oct
Flexhome Ukrainian Village • 2BR • Walkable + Private Balcony · Sleeps 6
A modern kitchen with stainless steel appliances, white cabinetry, and a black stove.

17. 2BR Apt with 2 Baths & Laundry

2BR Apt with 2 Baths & Laundry
Near West Side
10.0 out of 10, Exceptional, (2 reviews)
"This made our stay in Chicago very relaxing. Everything was as expected and I do not have any complaints! Would definitely stay here again!"
United States
Matthew H.
The price is NZ$541
includes taxes & fees
8 Nov - 9 Nov
2BR Apt with 2 Baths & Laundry
A modern living room with a blue sofa, a patterned rug, and a television.

18. Great Area Logan Square Apt Games Pets - Sleeps 5

Great Area Logan Square Apt Games Pets - Sleeps 5
Avondale
10.0 out of 10, Exceptional, (2 reviews)
"Place was nice and clean. Great communication from the host! Would stay here again!"
United States
Deborah J.
The price is NZ$354
includes taxes & fees
10 Nov - 11 Nov
Great Area Logan Square Apt Games Pets - Sleeps 5
A modern balcony with wicker furniture, a glass table, and a city skyline view.

19. Wabash 4BR - Pool, Free In & Out Parking 1

Wabash 4BR - Pool, Free In & Out Parking 1
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"Property is new and really nice. Super clean and well put together. Would stay here again."
United States
Devin D.
Wabash 4BR - Pool, Free In & Out Parking 1
A cabinet with two shelves; the top shelf holds two bowls, and the bottom shelf holds two stacks of plates.

20. 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.
River North Private Balcony With In and Out Parking
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 Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

8/10 Good
"It’s just loud at night when time to sleep"
Jill 1-night trip
Posted less than an hour ago
The Chicago Hotel Collection Ambassador Gold Coast

Find out more about Chicago

Everything you need to know about Chicago holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chicago holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Chicago holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chicago holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chicago holiday rentals we have selected for you start as low as NZ$143 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Chicago rentals

At Expedia, we put the best Chicago holiday 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 holiday.

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 holiday rentals in Chicago?

Yes, there are holiday rentals in Chicago close to Six Flags Great America, or you can select a more secluded option if you're looking for a relaxing stay. Tourists who visit Chicago like the notable monuments and acclaimed theatre 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 holiday rentals that Chicago has to offer?

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line: This highly rated holiday home rental in Chicago is located in the city centre, and has a balcony, a BBQ 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 that you can cook with friends or family. Other favourite homes for rent in Chicago are Sleeps 18 • 8BR • Game Room • Gym • Theater and LUXE 3 BR, 2 BA + Hot Tub.

How many holiday rentals are there in Chicago?

With 933 Expedia holiday rentals, you're guaranteed 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 holiday rentals like in Chicago?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chicago. Holiday rentals offer extras like WiFi and washers and dryers so you'll have everything you want. If you're concerned about a sanitised environment, holiday rentals can offer a sense of safety away from public hotel lifts and lobbies bustling with people while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular option for a small group gathering.