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Chicago Holiday Rentals

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Check prices for these dates

In two weeks
7 Aug - 9 Aug
In two months
18 Sept - 20 Sept
In three months
16 Oct - 18 Oct
In four months
13 Nov - 15 Nov

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, (1,229 reviews)
"Great location. Great views of the lake. Great pool, lounge area. Great restaurants right next door."
United States
Patricia
The price is HK$1,249
HK$1,696 total
includes taxes & fees
9 Aug - 10 Aug
Sentral Michigan Avenue
1 bedroom, iron/ironing board, travel cot, WiFi

LIVN West Loop Chicago Queen Superior Studio

LIVN West Loop Chicago Queen Superior Studio
Downtown Chicago
9.2 out of 10, Wonderful, (14 reviews)
"Highly recommend! Will be staying here again."
United States
Sheila M.
The price is HK$3,772
HK$5,048 total
includes taxes & fees
30 Jul - 31 Jul
LIVN West Loop Chicago Queen Superior Studio
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, (508 reviews)
"We only stayed one night but we definitely want to go back and stay at least two nights. It really was beautiful, clean and very secure."
United States
Martha
The price is HK$2,181
HK$2,754 total
includes taxes & fees
17 Aug - 18 Aug
Level Chicago – Old Town
TV, offices

LIVN Millennium Park Downtown Chicago 1 BR

LIVN Millennium Park Downtown Chicago 1 BR
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"Great location to sights, shops, and food."
United States
Adrianna W.
The price is HK$4,015
HK$5,372 total
includes taxes & fees
2 Aug - 3 Aug
LIVN Millennium Park Downtown Chicago 1 BR
Fitness facility

South Loop Rooftop With In & Out Parking 1

South Loop Rooftop With In & Out Parking 1
Downtown Chicago
9.0 out of 10, Wonderful, (2 reviews)
"We loved the property! It was well kept, clean, with a seamless check in and check out process! I wish the parking garage would have been closer but otherwise everything was great! Shout out to the host for his promptness with all my questions! I would recommend this place if they are looking for a place to stay! "
United States
Bridney K.
The price is HK$1,835
HK$4,394 total
includes taxes & fees
29 Jul - 30 Jul
South Loop Rooftop With In & Out Parking 1
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, (26 reviews)
"Great location. "
United States
Tom S.
The price is HK$3,106
HK$7,085 total
includes taxes & fees
2 Aug - 3 Aug
Modern West Loop Gem-City Views & Prime Location 6
Interior

River North Rooftop With In and Out Parking 3

River North Rooftop With In and Out Parking 3
Downtown Chicago
9.8 out of 10, Exceptional, (8 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.
The price is HK$2,078
HK$4,743 total
includes taxes & fees
19 Aug - 20 Aug
River North Rooftop With In and Out Parking 3
Property grounds

ENVITAE Hotel, 4BR Luxury Modern Apartments

ENVITAE Hotel, 4BR Luxury Modern Apartments
Near North Side
9.4 out of 10, Exceptional, (19 reviews)
"The property was clean and the location was great."
United States
Steven C.
The price is HK$4,706
HK$8,545 total
includes taxes & fees
30 Jul - 31 Jul
ENVITAE Hotel, 4BR Luxury Modern Apartments
Interior

Premium Urban 4BR - Perfect Mix of Comfort & Location

Premium Urban 4BR - Perfect Mix of Comfort & Location
Near North Side
10.0 out of 10, Exceptional, (4 reviews)
"Clean, comfortable, and stylish!"
United States
Maurya K.
The price is HK$5,262
HK$9,204 total
includes taxes & fees
30 Jul - 31 Jul
Premium Urban 4BR - Perfect Mix of Comfort & Location
TV, offices

LIVN West Loop Chicago 2 BR City View

LIVN West Loop Chicago 2 BR City View
Downtown Chicago
9.2 out of 10, Wonderful, (9 reviews)
"We spent most of this trip discussing our NEXT trip - this stay was one of the simplest, easiest, and most satisfying we've ever experienced with a short-term rental. Hands-down will stay again!Unit incredibly clean, close proximity to the areas we needed to be in, and the host was next-level communicative and kind! Thank you for making it so easy for us!"
United States
Stephanie G.
The price is HK$6,172
HK$8,330 total
includes taxes & fees
1 Aug - 2 Aug
LIVN West Loop Chicago 2 BR City View
1 bedroom, iron/ironing board, travel cot, WiFi

LIVN West Loop Chicago Classic Queen Studio

LIVN West Loop Chicago Classic Queen Studio
Downtown Chicago
10.0 out of 10, Exceptional, (6 reviews)
"check-in was a mess , everything else was fabulous"
United States
HollyAnn N.
The price is HK$2,086
HK$2,788 total
includes taxes & fees
3 Aug - 4 Aug
LIVN West Loop Chicago Classic Queen Studio
Dining

LIVN Millennium Park Downtown Chicago Prem Studio

LIVN Millennium Park Downtown Chicago Prem Studio
Downtown Chicago
10.0 out of 10, Exceptional, (3 reviews)
"The check in and out process was very quick. Communication with the host was great. "
United States
Raquel W.
LIVN Millennium Park Downtown Chicago Prem Studio
TV, offices

LIVN Millennium Park Downtown Chicago 2BR

LIVN Millennium Park Downtown Chicago 2BR
Downtown Chicago
10.0 out of 10, Exceptional, (5 reviews)
"Excellent location... Very cleaned....it is perfect"
United States
Granada
The price is HK$1,992
HK$2,697 total
includes taxes & fees
28 Jul - 29 Jul
LIVN Millennium Park Downtown Chicago 2BR
TV, offices

LIVN Millennium Park Downtown Chicago Superior 1BR

LIVN Millennium Park Downtown Chicago Superior 1BR
Downtown Chicago
10.0 out of 10, Exceptional, (2 reviews)
"Excelente, well located. Recommended."
United States
Sandra S.
LIVN Millennium Park Downtown Chicago Superior 1BR
Dining

LIVN Millennium Park Downtown Chicago Studio

LIVN Millennium Park Downtown Chicago Studio
Downtown Chicago
9.2 out of 10, Wonderful, (5 reviews)
"Great location, lovely furnishings and amenities."
United States
Georgina E.
The price is HK$1,945
HK$2,632 total
includes taxes & fees
28 Jul - 29 Jul
LIVN Millennium Park Downtown Chicago Studio
TV, offices

LIVN Millennium Park Downtown Chicago Superior 2 BR

LIVN Millennium Park Downtown Chicago Superior 2 BR
Downtown Chicago
9.4 out of 10, Exceptional, (6 reviews)
"We loved the location."
United States
Nicoll M.
LIVN Millennium Park Downtown Chicago Superior 2 BR
TV, offices

Modern West Loop Gem-City Views & Prime Location 4

Modern West Loop Gem-City Views & Prime Location 4
Downtown Chicago
9.6 out of 10, Exceptional, (12 reviews)
"Amazing accommodation"
United States
Jiri N.
The price is HK$2,910
HK$6,804 total
includes taxes & fees
9 Aug - 10 Aug
Modern West Loop Gem-City Views & Prime Location 4
Interior

Peaceful Cozy Beach View| 13 mins DT | 4 mins Lake

Peaceful Cozy Beach View| 13 mins DT | 4 mins Lake
Uptown
9.2 out of 10, Wonderful, (17 reviews)
"I don’t know if I recommend that place! ends up charging fees that make the total cost much higher than the nightly room rate."
United States
flor
The price is HK$1,035
HK$2,767 total
includes taxes & fees
28 Jul - 29 Jul
Peaceful Cozy Beach View| 13 mins DT | 4 mins Lake
Interior

Modern West Loop Gem-City Views & Prime Location 3

Modern West Loop Gem-City Views & Prime Location 3
Downtown Chicago
10.0 out of 10, Exceptional, (7 reviews)
"Loved the place 4 bedroom & 4 bathrooms was ideal for our stayGreat locationLoved the well stocked convenience store a block away "
United States
Tina Y.
Modern West Loop Gem-City Views & Prime Location 3
TV, offices

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, (4 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.
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

Warwick Allerton - Chicago

Warwick Allerton - Chicago

8/10 Good
"Other than a few things that were out of the staff’s control, it was an overall positive experience."
Colton 2-night trip
Posted 2 hours ago
Warwick Allerton - Chicago

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!

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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?

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 ENVITAE Hotel, 4BR Luxury Modern Apartments and Comfy 4 bedroom Apartment in the center of CHICAGO! 15 mins from Downtown!.

How many holiday rentals are there in Chicago?

With 936 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 Soldier 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.