Chicago Holiday Rentals

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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 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, (1,401 reviews)
"10/10 2nd time staying here!"
United States
Rosa
The price is NZ$284
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
8.8 out of 10, Excellent, (83 reviews)
"The bathroom was really clean. The beds were really comfortable"
United States
Jair
The price is NZ$485
includes taxes & fees
5 Nov - 6 Nov
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
The price is NZ$403
includes taxes & fees
23 Nov - 24 Nov
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
9.2 out of 10, Wonderful, (51 reviews)
"Clean room"
United States
Michael
The price is NZ$259
includes taxes & fees
5 Nov - 6 Nov
Wrigleyville Suites
A multi-story building with a fire escape, a pedestrian bridge, and a train on an elevated track.

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.
The price is NZ$447
includes taxes & fees
8 Nov - 9 Nov
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
The price is NZ$364
includes taxes & fees
11 Nov - 12 Nov
Chic Urban Retreat Near Wrigley Field w/Parking
A spacious lobby with high ceilings and a skylight, featuring marble columns and a central staircase.

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.
The price is NZ$354
includes taxes & fees
5 Nov - 6 Nov
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
The price is NZ$411
includes taxes & fees
9 Nov - 10 Nov
Chic Studio in the Heart of the Gold Coast
A modern living room with a sofa, a TV, and a dining area with stools.

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
The price is NZ$375
includes taxes & fees
9 Nov - 10 Nov
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.
The price is NZ$1,303
includes taxes & fees
26 Nov - 27 Nov
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.
The price is NZ$632
includes taxes & fees
18 Nov - 19 Nov
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.
The price is NZ$1,064
includes taxes & fees
11 Nov - 12 Nov
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
The price is NZ$792
includes taxes & fees
16 Nov - 17 Nov
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.
The price is NZ$688
includes taxes & fees
12 Nov - 13 Nov
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.
The price is NZ$390
includes taxes & fees
26 Nov - 27 Nov
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
The price is NZ$1,456
includes taxes & fees
22 Nov - 23 Nov
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.
The price is NZ$1,126
includes taxes & fees
19 Nov - 20 Nov
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.
The price is NZ$242
includes taxes & fees
30 Nov - 1 Dec
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
The price is NZ$940
includes taxes & fees
5 Nov - 6 Nov
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
The price is NZ$494
includes taxes & fees
9 Nov - 10 Nov
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 holiday rentals that suit your style

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Cabins
Cabins
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Aparthotels
Aparthotels

Top Chicago Hotel Reviews

A modern hotel lobby with a long blue sofa, numbered cushions, and hanging planters.
Hilton Vacation Club Hotel Blake Chicago

Hilton Vacation Club Hotel Blake Chicago

Hilton Vacation Club Hotel Blake Chicago
Downtown Chicago

10/10 Excellent

The hotel has been reburbished beautifully. Staff have been amazing letting us hang out in the lounge waiting for our train departure. Great location, fantastic cafe next door, great bars in the area. Only a short walk to Michigan Avenue for hop on hop off bus.
Australia
Cherrie
Reviewed October 12, 2024
Hilton Vacation Club Hotel Blake Chicago

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$241 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.

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.

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