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Chicago Holiday Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 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, (1,344 reviews)
"Great venue"
United States
Arthur Noel
The price is NZ$415
includes taxes & fees
26 Oct - 27 Oct
Sentral Michigan Avenue
Lake

2. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
8.4 out of 10, Very good, (45 reviews)
"Great location and room"
United States
Miriam
The price is NZ$477
includes taxes & fees
30 Sept - 1 Oct
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, (532 reviews)
"Location and facility was very nice"
United States
Brian
The price is NZ$666
includes taxes & fees
29 Oct - 30 Oct
Level Chicago – Old Town
A modern living room with a fireplace, a flat-screen TV, a sofa, and a dining area.

4. 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$491
includes taxes & fees
13 Oct - 14 Oct
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.

5. LIVN West Loop Chicago Queen Superior Studio

LIVN West Loop Chicago Queen Superior Studio
Downtown Chicago
9.6 out of 10, Exceptional, (25 reviews)
"Incredible location, very clean and easy! Would book again!"
United States
Andrea K.
The price is NZ$494
includes taxes & fees
1 Oct - 2 Oct
LIVN West Loop Chicago Queen Superior Studio
A modern living room with a sofa, a coffee table, a floor lamp, a television, and a black cabinet.

6. Modern 1BR in Prime West Loop Location

Modern 1BR in Prime West Loop Location
Downtown Chicago
The price is NZ$748
includes taxes & fees
29 Oct - 30 Oct
Modern 1BR in Prime West Loop Location
A compact laundry room with a front-loading washer and dryer, a framed picture on the wall, and a towel rack.

7. Plymouth Collection: 3BD 2BA High Floor with Gym

Plymouth Collection: 3BD 2BA High Floor with Gym
Downtown Chicago
9.6 out of 10, Exceptional, (4 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$759
includes taxes & fees
30 Sept - 1 Oct
Plymouth Collection: 3BD 2BA High Floor with Gym
A hotel room with a bed, two bedside lamps, a wall-mounted artwork, and a small table with a lamp.

8. 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$539
includes taxes & fees
27 Oct - 28 Oct
2BR Apt with 2 Baths & Laundry
A room with a round table, two chairs, a vase with flowers, a plate with food, and a window with blinds.

9. LIVN Millennium Park Downtown Chicago Studio

LIVN Millennium Park Downtown Chicago Studio
Downtown Chicago
9.4 out of 10, Exceptional, (11 reviews)
"Great location, lovely furnishings and amenities."
United States
Georgina E.
The price is NZ$524
includes taxes & fees
1 Oct - 2 Oct
LIVN Millennium Park Downtown Chicago Studio
A modern kitchen with a large island, a built-in refrigerator, and a view of the city through large windows.

10. 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$683
includes taxes & fees
12 Oct - 13 Oct
River North Private Balcony With In and Out Parking
A rooftop terrace with a brick wall, large windows, and a metal railing.

11. 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, (59 reviews)
"It was exactly what we were hoping for. Cute, clean, comfy. Great!!"
United States
Melissa M.
The price is NZ$476
includes taxes & fees
5 Oct - 6 Oct
Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
A modern living room with a brick wall, large windows, a flat-screen TV, a sofa, a coffee table, and a side table.

12. 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$1,571
includes taxes & fees
17 Oct - 18 Oct
River North Rooftop With In and Out Parking 6
Communal lounging

13. Cozy Studio Suite, Steps from River North & Shops

Cozy Studio Suite, Steps from River North & Shops
Near North Side
9.4 out of 10, Exceptional, (3 reviews)
"Clean apartment in cozy neighborhood"
United States
Susannah R.
Cozy Studio Suite, Steps from River North & Shops
A modern living room with a fireplace, a dining area with a wooden table and chairs, and a kitchen with a white railing.

14. Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
7.8 out of 10, Good, (61 reviews)
"We had a great stay! Perfect location for cubs games and hanging out in wrigleyville."
United States
Kate
The price is NZ$308
includes taxes & fees
30 Sept - 1 Oct
Wrigleyville Suites
A modern bedroom with a bed, a sofa, and a hanging plant.

15. Cozy studio in Andersonville Chicago

Cozy studio in Andersonville Chicago
Edgewater
9.6 out of 10, Exceptional, (99 reviews)
"The room was clean, comfortable, and well decorated. The location is walkable and safe. The hosts are very kind and accommodating. We would stay there again."
United States
Katie K.
The price is NZ$256
includes taxes & fees
26 Oct - 27 Oct
Cozy studio in Andersonville Chicago
A bedroom with a bed, a wardrobe, a bench, and a floor lamp.

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

Wabash 4BR - Pool, Free In & Out Parking 4
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"Nice place to stay."
United States
William H.
The price is NZ$1,212
includes taxes & fees
29 Sept - 30 Sept
Wabash 4BR - Pool, Free In & Out Parking 4
A modern kitchen with wooden cabinets, a stainless steel dishwasher, a microwave, a coffee maker, and a toaster.

17. Smart Simple and Spacious 4BR Apt

Smart Simple and Spacious 4BR Apt
Near South Side
8.2 out of 10, Very good, (12 reviews)
"Everything was exactly as described."
United States
Sydney D.
The price is NZ$687
includes taxes & fees
29 Sept - 30 Sept
Smart Simple and Spacious 4BR Apt
A modern apartment with a living area, kitchen, and large windows offering city views.

18. 3BR Luxury Suite w/Gym and Balcony

3BR Luxury Suite w/Gym and Balcony
Downtown Chicago
9.6 out of 10, Exceptional, (36 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
3BR Luxury Suite w/Gym and Balcony
A modern kitchen with white cabinets, a central island with stools, a microwave, and a refrigerator.

19. 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$419
includes taxes & fees
29 Sept - 30 Sept
3BR Complete and Spacious Apartment in Ideal Spot
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.
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

Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

10/10 Excellent
"Clean"
Kenda 2-night trip
Posted less than an hour ago
Hyatt Regency O'Hare 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$129 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 LUXE 3 BR, 2 BA + Hot Tub and Cozy 3-bedroom house in family-oriented Melrose Park..

How many holiday rentals are there in Chicago?

With 934 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.