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

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, (1,392 reviews)
"10/10 2nd time staying here!"
United States
Rosa
The price is NZ$282
includes taxes & fees
22 Nov - 23 Nov
Sentral Michigan Avenue
A modern living room with a sofa, a round coffee table, and a dining area with a table and chairs.

2. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (76 reviews)
"Amazing property would stay here again. Looks exactly like pics!!"
United States
Felipe
The price is NZ$438
includes taxes & fees
16 Nov - 17 Nov
Kasa Lake Shore Chicago
A modern living room with a fireplace, a dining area with a wooden table and chairs, and a kitchen with a white railing.

3. Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
9.4 out of 10, Exceptional, (48 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$310
includes taxes & fees
2 Nov - 3 Nov
Wrigleyville Suites
A modern kitchen with a large island, bar stools, and a city view.

4. Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (553 reviews)
"Super clean and friendly staff! Would definitely stay here again"
United States
Robert Edward
The price is NZ$425
includes taxes & fees
4 Nov - 5 Nov
Level Chicago – Old Town
A multi-story building with a fire escape, a pedestrian bridge, and a train on an elevated track.

5. 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$391
includes taxes & fees
2 Nov - 3 Nov
LIVN Millennium Park Downtown Chicago Studio
A rooftop terrace with a brick wall, large windows, and a metal railing.

6. 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$479
includes taxes & fees
3 Nov - 4 Nov
Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
A wooden dining table with two chairs, a potted plant, and a painting on the wall.

7. 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$456
includes taxes & fees
10 Nov - 11 Nov
Chic Studio in the Heart of the Gold Coast
A modern living room with a fireplace, a flat-screen TV, a sofa, and a dining area.

8. 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$361
includes taxes & fees
11 Nov - 12 Nov
Chic Urban Retreat Near Wrigley Field w/Parking
A table with a book titled "MANIFEST & EXECUTE," a cup of coffee, a bowl of raspberries, a small potted plant, and a vase with white flowers.

9. 2BR Fitness Pad • Private Gym • Sleeps 7

2BR Fitness Pad • Private Gym • Sleeps 7
Irving Park
9.4 out of 10, Exceptional, (8 reviews)
"Great property in a central location. Neighborhood was quiet and safe with good parks nearby. Apartment had good amenities and perfect for our stay. Communication with host was excellent"
United States
Carey M.
The price is NZ$535
includes taxes & fees
1 Nov - 2 Nov
2BR Fitness Pad • Private Gym • Sleeps 7
A modern living room with a brick wall, large windows, a flat-screen TV, a sofa, a coffee table, and a side table.

10. River North Rooftop With In and Out Parking 6

River North Rooftop With In and Out Parking 6
Downtown Chicago
9.0 out of 10, Wonderful, (2 reviews)
"Host was amazing, very responsive. VRBO was spotless! Great location! Would definitely stay here again."
United States
Amy L.
River North Rooftop With In and Out Parking 6
A rooftop terrace with a brick wall, large windows, and a metal railing.

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

Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake
Uptown
9.4 out of 10, Exceptional, (31 reviews)
"Very nice and clean place in a great location if you are going to Wrigley"
United States
Paul J.
The price is NZ$484
includes taxes & fees
4 Nov - 5 Nov
Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake
A dining area with a round wooden table, four upholstered chairs, a vase with white flowers, and two wall-mounted light fixtures.

12. Studio Near Wrigley • Sleeps 4 • Games • Fireplace

Studio Near Wrigley • Sleeps 4 • Games • Fireplace
Irving Park
10.0 out of 10, Exceptional, (7 reviews)
"Clean, comfortable bed, plenty of amenities. Steps and entry were a little awkward. Street parking only unless you paid extra for their garage which was a very tight fit for my sedan. Note older building so could hear neighbors but it wasn’t intrusive. Also note 3.6 miles to Wrigley was a 25 minute drive. Overall great place and would stay again."
United States
Meagan C.
The price is NZ$483
includes taxes & fees
5 Nov - 6 Nov
Studio Near Wrigley • Sleeps 4 • Games • Fireplace
A modern living room with a sofa, a TV, and a dining area with stools.

13. 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$434
includes taxes & fees
9 Nov - 10 Nov
3BR Complete and Spacious Apartment in Ideal Spot
A modern living room with a spiral staircase, a green sofa, a round coffee table, and a large abstract painting on the wall.

14. 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$835
includes taxes & fees
16 Nov - 17 Nov
Luxury River North Loft | Walk to Mag Mile, Riverwalk & Top Restaurants
A hotel room with a large bed, a desk, a chair, a lamp, and artwork on the wall.

15. 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$331
includes taxes & fees
2 Nov - 3 Nov
Flexhome Ukrainian Village • 2BR • Walkable + Private Balcony · Sleeps 6
A neatly arranged bedroom with a bed, bedside tables, and abstract wall art.

16. Hyde Park Trendy Studio Apartment in Good Spot

Hyde Park Trendy Studio Apartment in Good Spot
Hyde Park
10.0 out of 10, Exceptional, (1 review)
"Such a cozy stay! Definitely recommend!"
United States
Angelina
The price is NZ$316
includes taxes & fees
11 Nov - 12 Nov
Hyde Park Trendy Studio Apartment in Good Spot
A modern living room with a blue sofa, a patterned rug, and a television.

17. 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$378
includes taxes & fees
10 Nov - 11 Nov
Great Area Logan Square Apt Games Pets - Sleeps 5
A rooftop terrace with a fire pit, seating area, and a city skyline view.

18. 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
9.8 out of 10, Exceptional, (6 reviews)
"Very happy with our stay. Loved the rooftop views! The host was very friendly and welcoming."
United States
Jessica C.
The price is NZ$427
includes taxes & fees
8 Nov - 9 Nov
Penthouse and Private Rooftop with Skyline Views, Grill, and Fire Pit - Sleeps 6
A modern kitchen with white cabinets, stainless steel appliances, and a dining area with a gray sofa and patterned cushions.

19. 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.
The price is NZ$703
includes taxes & fees
1 Nov - 2 Nov
Plymouth Collection: 3BD 2BA High Floor with Gym
A modern kitchen with a large island, a built-in refrigerator, and a view of the city through large windows.

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.
The price is NZ$714
includes taxes & fees
18 Nov - 19 Nov
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

Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

8/10 Good
"Quick stay for overnight connection at ORD. Hotel was very convenient as you can walk from terminal to the hotel with clear signage. It was expensive but worth it to get few hours of sleep."
Wissam 1-night trip
Posted 2 hours ago
Hilton Chicago O'Hare Airport

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$139 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.