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
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

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, (1,366 reviews)
"Perfect location to stay at if attending the bears games !"
United States
Jacob
The price is NZ$326
includes taxes & fees
10 Nov - 11 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, (63 reviews)
"Location is perfect"
United States
Mary
The price is NZ$485
includes taxes & fees
1 Nov - 2 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, (540 reviews)
"Great location, very clean, loved the gym and cafe!"
United States
Kerry
The price is NZ$623
includes taxes & fees
11 Nov - 12 Nov
Level Chicago – Old Town
A modern living room with a brick wall, large windows, a flat-screen TV, a sofa, a coffee table, and a side table.

4. 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.
The price is NZ$682
includes taxes & fees
3 Nov - 4 Nov
River North Rooftop With In and Out Parking 6
A room with a round table, two chairs, a vase with flowers, a plate with food, and a window with blinds.

5. LIVN Millennium Park Downtown Chicago Studio

LIVN Millennium Park Downtown Chicago Studio
Downtown Chicago
9.4 out of 10, Exceptional, (11 reviews)
"This spot is great and very close to The Bean. Lots of restaurants and bars in walking distance and there’s a great coffee shop right next door too. Would definitely stay here again!!"
United States
Karlise J.
The price is NZ$608
includes taxes & fees
14 Oct - 15 Oct
LIVN Millennium Park Downtown Chicago Studio
A spacious lobby with a sectional sofa, a dining area, and large windows.

6. 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
The price is NZ$939
includes taxes & fees
14 Oct - 15 Oct
South Loop Rooftop With In and Out Parking 3
A hotel room with a bed, two bedside lamps, a wall-mounted artwork, and a small table with a lamp.

7. 2BR Apt with 2 Baths & Laundry

2BR Apt with 2 Baths & Laundry
Near West Side
10.0 out of 10, Exceptional, (1 review)
"The property was very clean and perfect for our overnight stay. Thank you"
United States
michele
The price is NZ$405
includes taxes & fees
2 Nov - 3 Nov
2BR Apt with 2 Baths & Laundry
A bedroom with a bed, a nightstand, a lamp, and a window with blinds.

8. Downtown Chicago Stay with Free In & Out Parking 1

Downtown Chicago Stay with Free In & Out Parking 1
Downtown Chicago
9.4 out of 10, Exceptional, (6 reviews)
"Spacious, free parking, family friendly"
United States
Majid
The price is NZ$950
includes taxes & fees
29 Oct - 30 Oct
Downtown Chicago Stay with Free In & Out Parking 1
A modern living room with a fireplace, a dining area with a wooden table and chairs, and a kitchen with a white railing.

9. Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
7.6 out of 10, Good, (63 reviews)
"We had a great stay! Perfect location for cubs games and hanging out in wrigleyville."
United States
Kate
The price is NZ$327
includes taxes & fees
3 Nov - 4 Nov
Wrigleyville Suites
A modern living room with a fireplace, a flat-screen TV, a sofa, and a dining area.

10. Chic Urban Retreat Near Wrigley Field w/Parking

Chic Urban Retreat Near Wrigley Field w/Parking
Lakeview
10.0 out of 10, Exceptional, (68 reviews)
"Hosts were great, location is great, and it was a great stay."
United States
Ryan G.
The price is NZ$422
includes taxes & fees
13 Oct - 14 Oct
Chic Urban Retreat Near Wrigley Field w/Parking
A modern kitchen with a marble island, wooden cabinets, and a dining area with a table and chairs.

11. River North Rooftop With In and Out Parking 3

River North Rooftop With In and Out Parking 3
Downtown Chicago
9.0 out of 10, Wonderful, (10 reviews)
"Not a bad thing to say about this experience. Host was extremely responsive and helpful, looked exactly like the pictures, had everything we needed, location was perfect and the included parking was such a perk! Highly recommend staying here. I hope to be back! "
United States
Kara B.
River North Rooftop With In and Out Parking 3
A rooftop terrace with a brick wall, large windows, and a metal railing.

12. 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$519
includes taxes & fees
12 Oct - 13 Oct
Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
A rooftop terrace with a fire pit, seating area, and a city skyline view.

13. 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.
Penthouse and Private Rooftop with Skyline Views, Grill, and Fire Pit - Sleeps 6
A bedroom with a bed, bedside tables, a ceiling fan, framed pictures, and a window.

14. Stylish Gold Coast 1BR with Vintage Flair

Stylish Gold Coast 1BR with Vintage Flair
Downtown Chicago
The price is NZ$608
includes taxes & fees
9 Nov - 10 Nov
Stylish Gold Coast 1BR with Vintage Flair
A modern kitchen with white cabinets, a stainless steel refrigerator, a built-in oven, and a window above the sink.

15. Flexhome East Village • Modern 2BR • Quiet Street

Flexhome East Village • Modern 2BR • Quiet Street
West Town
9.6 out of 10, Exceptional, (26 reviews)
"Great location! "
United States
Andrea B.
Flexhome East Village • Modern 2BR • Quiet Street
A hotel room with a geometric-patterned wall, a bed with white bedding and a beige throw, two bedside lamps, and a window with blinds.

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$301
includes taxes & fees
2 Nov - 3 Nov
Flexhome Ukrainian Village • 2BR • Walkable + Private Balcony · Sleeps 6
A modern kitchen with white cabinets, a central island with stools, a microwave, and a refrigerator.

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.
The price is NZ$498
includes taxes & fees
19 Oct - 20 Oct
3BR Complete and Spacious Apartment in Ideal Spot
A hotel room with a bed, two bedside tables, and three wall-mounted paintings.

18. Stylish Japanese-Themed 2BR Apt Close to Downtown

Stylish Japanese-Themed 2BR Apt Close to Downtown
Downtown Chicago
The price is NZ$538
includes taxes & fees
2 Nov - 3 Nov
Stylish Japanese-Themed 2BR Apt Close to Downtown
A modern bedroom with a bed, a sofa, and a hanging plant.

19. Cozy studio in Andersonville Chicago

Cozy studio in Andersonville Chicago
Edgewater
9.6 out of 10, Exceptional, (102 reviews)
"Great location and amazing space! Perfect for visiting the city to apartment search for an upcoming move."
United States
Audrey A.
The price is NZ$248
includes taxes & fees
2 Nov - 3 Nov
Cozy studio in Andersonville Chicago
A hotel room with a bed, a view of a cityscape, and a window with curtains.

20. Elegant Style Loft Montrose|13 mins DT|4 mins Lake

Elegant Style Loft Montrose|13 mins DT|4 mins Lake
Uptown
8.6 out of 10, Excellent, (11 reviews)
"Great location and great place! "
United States
Ryinne P.
The price is NZ$406
includes taxes & fees
12 Oct - 13 Oct
Elegant Style Loft Montrose|13 mins DT|4 mins Lake
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
"Hotel was unique and enjoyed the location. Room was very basic but functional. Lobby was very welcoming."
Lindsey Marie 3-night trip
Posted 1 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$145 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.