Chicago Holiday Rentals

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Check prices for these dates

In two weeks
10 Apr - 12 Apr
In two months
22 May - 24 May
In three months
19 Jun - 21 Jun
In four months
17 Jul - 19 Jul

Our top choices for Chicago holiday rentals

Indoor pool

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,114 reviews)
"Clean spacious my go to vacation spot all year around "
United States
xavier
The price is HK$858
HK$1,237 total
includes taxes & fees
1 Apr - 2 Apr
Sentral Michigan Avenue
Full-sized fridge, microwave, oven, stovetop

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (451 reviews)
"Great value, friendly staff"
United States
Marcus
The price is HK$1,285
HK$1,702 total
includes taxes & fees
29 Mar - 30 Mar
Level Chicago – Old Town
TV, offices

Chicago-Themed 1BR in a Central Spot near Downtown

Chicago-Themed 1BR in a Central Spot near Downtown
Downtown Chicago
The price is HK$1,174
HK$2,194 total
includes taxes & fees
2 Apr - 3 Apr
Chicago-Themed 1BR in a Central Spot near Downtown
TV, offices

Sun-Drenched 1BR Apartment

Sun-Drenched 1BR Apartment
Downtown Chicago
10.0 out of 10, Exceptional, (2 reviews)
"Host was very friendly and informative. Place was clean and close to lots of fun. Trains loud and busy but knew that going in. "
United States
Tyler B.
The price is HK$1,135
HK$2,158 total
includes taxes & fees
29 Mar - 30 Mar
Sun-Drenched 1BR Apartment
Dining room

Kasa Magnificent Mile Chicago

Kasa Magnificent Mile Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (719 reviews)
"Great place "
United States
Lamees
Kasa Magnificent Mile Chicago
1 bedroom, iron/ironing board, travel cot, WiFi

West Loop Living – Bright 1BR

West Loop Living – Bright 1BR
Downtown Chicago
10.0 out of 10, Exceptional, (8 reviews)
"Great communication and hosts. Location and unit was perfect."
United States
Greg C.
The price is HK$1,049
HK$2,038 total
includes taxes & fees
29 Mar - 30 Mar
West Loop Living – Bright 1BR
Desk, iron/ironing board, travel cot, WiFi

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, (5 reviews)
"We had a wonderful stay at this Vrbo! The home was spotless, cozy, and exactly as described. The host was friendly, responsive, and made everything easy from check-in to check-out. We would absolutely stay here again. Highly recommend!"
United States
Brianna K.
The price is HK$885
HK$1,718 total
includes taxes & fees
29 Mar - 30 Mar
Chic Studio in the Heart of the Gold Coast
Interior

River North Rooftop With In and Out Parking 3

River North Rooftop With In and Out Parking 3
Downtown Chicago
9.6 out of 10, Exceptional, (4 reviews)
"We had a very comfortable stay here. The hosts are exceptionally communicative and helpful. Loved having a place to park my car, and the hosts set it up so my license plate was recognized at the gate so that parking was free. The unit was very clean and spacious. Note, the kitchen does not have pots or pans to cook, so plan on eating out!"
United States
Jennifer M.
The price is HK$1,252
HK$3,575 total
includes taxes & fees
14 Apr - 15 Apr
River North Rooftop With In and Out Parking 3
TV, offices

Modern Comfort: 1BR Unit w/ Laundry

Modern Comfort: 1BR Unit w/ Laundry
Downtown Chicago
9.4 out of 10, Exceptional, (16 reviews)
"Great host comfortable bed close to restaurants and parks"
United States
Alana C.
The price is HK$838
HK$1,761 total
includes taxes & fees
29 Mar - 30 Mar
Modern Comfort: 1BR Unit w/ Laundry
TV, offices

Modern West Loop Gem-City Views & Prime Location 4

Modern West Loop Gem-City Views & Prime Location 4
Downtown Chicago
10.0 out of 10, Exceptional, (8 reviews)
"Amazing accommodation"
United States
Jiri N.
Modern West Loop Gem-City Views & Prime Location 4
1 bedroom, WiFi, bed sheets

1BR Modern Luxe Apt with In-Unit Laundry

1BR Modern Luxe Apt with In-Unit Laundry
Downtown Chicago
8.0 out of 10, Very good, (2 reviews)
"Great experience for me and my wife I would definitely come back "
United States
ShowtimeFam1
The price is HK$1,276
HK$2,362 total
includes taxes & fees
8 Apr - 9 Apr
1BR Modern Luxe Apt with In-Unit Laundry
1 bedroom, iron/ironing board, travel cot, WiFi

LIVN West Loop Chicago Queen Superior Studio

LIVN West Loop Chicago Queen Superior Studio
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"The service was top notch at this property. The hosts were super responsive and professional. The location was incredible. Loved being able to cook in the apartment. The apartment was newly renovated and very urban chic. "
United States
Michelle R.
The price is HK$1,065
HK$1,443 total
includes taxes & fees
3 Apr - 4 Apr
LIVN West Loop Chicago Queen Superior Studio
TV, offices

Stylish Gold Coast 1BR with Vintage Flair

Stylish Gold Coast 1BR with Vintage Flair
Downtown Chicago
The price is HK$1,057
HK$2,037 total
includes taxes & fees
7 Apr - 8 Apr
Stylish Gold Coast 1BR with Vintage Flair
Interior

Near Lake and Museum • Modern • Game Area

Near Lake and Museum • Modern • Game Area
South Shore
The price is HK$1,096
HK$4,733 total
includes taxes & fees
26 Mar - 27 Mar
Near Lake and Museum • Modern • Game Area
Lounge

Kasa River North Chicago

Kasa River North Chicago
4.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (187 reviews)
"Nice area if you are renting a car, be aware that you would have to pay for street parking or go over a few blocks and park in a parking lot."
United States
Daysha
Kasa River North Chicago
TV, offices

Modern West Loop Gem-City Views & Prime Location 6

Modern West Loop Gem-City Views & Prime Location 6
Downtown Chicago
10.0 out of 10, Exceptional, (17 reviews)
"Great place"
United States
Daniel L.
The price is HK$1,542
HK$4,841 total
includes taxes & fees
29 Mar - 30 Mar
Modern West Loop Gem-City Views & Prime Location 6
Iron/ironing board, travel cot, WiFi, bed sheets

Cozy Well-Equipped Studio Apartment

Cozy Well-Equipped Studio Apartment
Hyde Park
10.0 out of 10, Exceptional, (1 review)
"Wow, this is a wonderful Place to stay. The host Is very responsive and friendly The apartment is immaculate I recommend this place highly . "
United States
pnina
The price is HK$564
HK$1,323 total
includes taxes & fees
26 Mar - 27 Mar
Cozy Well-Equipped Studio Apartment
Interior

10 Minutes to Downtown Chicago - Sleeps 12 - King Beds - Games and Arcades

10 Minutes to Downtown Chicago - Sleeps 12 - King Beds - Games and Arcades
Lawndale
8.8 out of 10, Excellent, (3 reviews)
"Great stay, perfect for our group of 6, everyone had there own room! Necessities right around the corner if needed Cermack rd a few feet away, gets you about everywhere! We wanted a real life Chicago experience, and it was great. Owner very responsive! Permit on street parking pretty accessible most times. Definitely will stay again!"
United States
Beth
The price is HK$845
HK$2,617 total
includes taxes & fees
1 Apr - 2 Apr
10 Minutes to Downtown Chicago - Sleeps 12 - King Beds - Games and Arcades
Property grounds

2-bedroom apartment just 2 minutes drive to Wrigley Field

2-bedroom apartment just 2 minutes drive to Wrigley Field
North Center
9.6 out of 10, Exceptional, (65 reviews)
"Nice property, great location, super helpful host!"
United States
Carin O.
The price is HK$1,050
HK$2,590 total
includes taxes & fees
29 Mar - 30 Mar
2-bedroom apartment just 2 minutes drive to Wrigley Field
Interior

Your Perfect 2BR Home

Your Perfect 2BR Home
Near West Side
8.4 out of 10, Very good, (15 reviews)
"Great location! "
United States
Kourtney K.
The price is HK$689
HK$1,734 total
includes taxes & fees
26 Mar - 27 Mar
Your Perfect 2BR Home
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 Wade

The Wade

10/10 Excellent
"Great place to stay. Staff is very friendly "
Dequan 2-night trip
Posted 1 hour ago
The Wade

Find out more about Chicago

Search for holiday rentals in Chicago on Expedia! You can easily find your home rentals, villas, holiday apartments in Chicago using one of the methods below:

  • View our selection of featured holiday rentals in Chicago
  • Use the map to find apartments and other holiday homes in the Chicago neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chicago while they last

Look no further and take a look at our great range of rental properties in Chicago!

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 art 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?

A Home Away From Home!: This highly rated holiday home rental in Chicago offers a fireplace, a garden and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop and a microwave. Other favourite homes for rent in Chicago are HUGE 1700 sqft 3bd West Loop Penthouse w/ Balcony and Comfy 4 bedroom Apartment in the center of CHICAGO! 15 mins from Downtown!.

How many holiday rentals are there in Chicago?

With 939 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 Michigan Avenue and Wrigley Field.

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.