Chicago Vacation Rentals

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Our top choices for Chicago vacation rentals

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,179 reviews)
"Great location"
United States
Karen
The price is ¥31,814
¥42,022 total
includes taxes & fees
Jul 2 - Jul 3
Sentral Michigan Avenue

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (484 reviews)
"Staff was amazing and the apartment building was phenomenally clean!"
United States
Seke
The price is ¥48,163
¥60,468 total
includes taxes & fees
Jun 30 - Jul 1
Level Chicago – Old Town

Gold Coast Hideaway | Vintage & Inviting Studio

Gold Coast Hideaway | Vintage & Inviting Studio
Downtown Chicago
The price is ¥28,191
¥48,082 total
includes taxes & fees
Jun 18 - Jun 19
Gold Coast Hideaway | Vintage & Inviting Studio

Stylish Japanese-Themed 2BR Apt Close to Downtown

Stylish Japanese-Themed 2BR Apt Close to Downtown
Downtown Chicago
The price is ¥53,196
¥85,877 total
includes taxes & fees
Jun 15 - Jun 16
Stylish Japanese-Themed 2BR Apt Close to Downtown

Modern 3BR Apartment Near North Ave Shops

Modern 3BR Apartment Near North Ave Shops
Near North Side
The price is ¥107,667
¥185,728 total
includes taxes & fees
Jun 12 - Jun 13
Modern 3BR Apartment Near North Ave Shops

Downtown Chicago Stay with Free In & Out Parking 1

Downtown Chicago Stay with Free In & Out Parking 1
Downtown Chicago
The price is ¥49,692
¥109,931 total
includes taxes & fees
Jul 1 - Jul 2
Downtown Chicago Stay with Free In & Out Parking 1

3BR Luxury Suite w/Gym and Balcony

3BR Luxury Suite w/Gym and Balcony
Downtown Chicago
9.4 out of 10, Exceptional, (28 reviews)
"The apartment is in a good location, close to restaurants and bars. There is a nice park not far away and we had a lovely stay. "
United States
shayna j.
The price is ¥154,492
¥258,054 total
includes taxes & fees
Jun 26 - Jun 27
3BR Luxury Suite w/Gym and Balcony

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, (23 reviews)
"Everything was walking distance and had everything needed for a comfortable stay "
United States
Daniel
The price is ¥44,914
¥118,731 total
includes taxes & fees
Jun 7 - Jun 8
Modern West Loop Gem-City Views & Prime Location 6

Spacious 4BR Central Apartment w/ Skyline Views

Spacious 4BR Central Apartment w/ Skyline Views
Near North Side
10.0 out of 10, Exceptional, (17 reviews)
"Great location, comfortable room, welcoming host."
United States
Treseanne A.
The price is ¥93,810
¥169,024 total
includes taxes & fees
Jun 18 - Jun 19
Spacious 4BR Central Apartment w/ Skyline Views

River North Rooftop With In and Out Parking 1

River North Rooftop With In and Out Parking 1
Downtown Chicago
9.8 out of 10, Exceptional, (6 reviews)
"Awesome location, great place would definitely recommend will hopefully return"
United States
lucas c.
River North Rooftop With In and Out Parking 1

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 ¥39,180
¥89,441 total
includes taxes & fees
Jun 28 - Jun 29
River North Rooftop With In and Out Parking 6

West Loop Living – Bright 1BR

West Loop Living – Bright 1BR
Downtown Chicago
10.0 out of 10, Exceptional, (11 reviews)
"Great spot next to the green line train a few restaurants and a Starbucks right up the street I will book again for sure "
United States
2k G.
The price is ¥28,828
¥51,600 total
includes taxes & fees
Jun 4 - Jun 5
West Loop Living – Bright 1BR

LIVN Millennium Park Downtown Chicago 2BR

LIVN Millennium Park Downtown Chicago 2BR
Downtown Chicago
10.0 out of 10, Exceptional, (2 reviews)
"Excellent location... Very cleaned....it is perfect"
United States
Granada
The price is ¥67,849
¥91,053 total
includes taxes & fees
Jun 2 - Jun 3
LIVN Millennium Park Downtown Chicago 2BR

LIVN West Loop Chicago 2 BR City View

LIVN West Loop Chicago 2 BR City View
Downtown Chicago
9.4 out of 10, Exceptional, (3 reviews)
"Super clean, great communication! Thanks for a great stay."
United States
Tracey L.
The price is ¥50,011
¥67,164 total
includes taxes & fees
Jun 4 - Jun 5
LIVN West Loop Chicago 2 BR City View

Sunlit 1BR Apartment | Warm & Welcoming Space

Sunlit 1BR Apartment | Warm & Welcoming Space
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 ¥21,979
¥42,004 total
includes taxes & fees
Jun 3 - Jun 4
Sunlit 1BR Apartment | Warm & Welcoming Space

1BR Modern Luxe Apt with In-Unit Laundry

1BR Modern Luxe Apt with In-Unit Laundry
Downtown Chicago
8.8 out of 10, Excellent, (3 reviews)
"Great experience for me and my wife I would definitely come back "
United States
ShowtimeFam1
The price is ¥28,191
¥50,855 total
includes taxes & fees
Jun 4 - Jun 5
1BR Modern Luxe Apt with In-Unit Laundry

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, (1 review)
"Nice place, clean property, great views "
United States
Zach L.
The price is ¥134,105
¥229,165 total
includes taxes & fees
Jun 26 - Jun 27
Premium Urban 4BR - Perfect Mix of Comfort & Location

ENVITAE Hotel, 4BR Luxury Modern Apartments

ENVITAE Hotel, 4BR Luxury Modern Apartments
Near North Side
10.0 out of 10, Exceptional, (11 reviews)
The price is ¥96,040
¥173,937 total
includes taxes & fees
Jun 25 - Jun 26
ENVITAE Hotel, 4BR Luxury Modern Apartments

Cozy 2BR with King Beds + Full Kitchen

Cozy 2BR with King Beds + Full Kitchen
Portage Park
2.0 out of 10, (1 review)
The price is ¥20,068
¥41,961 total
includes taxes & fees
Jun 10 - Jun 11
Cozy 2BR with King Beds + Full Kitchen

2BR Fitness Pad • Private Gym • Sleeps 7

2BR Fitness Pad • Private Gym • Sleeps 7
Irving Park
The price is ¥14,334
¥50,847 total
includes taxes & fees
Jun 3 - Jun 4
2BR Fitness Pad • Private Gym • Sleeps 7
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

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:

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

Frequently asked questions

Can I find vacation rentals in Chicago?

Yes, we give you a choice of vacation rentals in Chicago near Six Flags Great America, or you can choose a more secluded option if you want a relaxing stay. Tourists who visit Chicago like the notable monuments and entertainment choices. 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 vacation rentals in Chicago?

ENVITAE Hotel, 4BR Luxury Modern Apartments: This highly rated vacation home rental in Chicago is located in the city center and offers a barbecue grill, air-conditioning, and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Other favorite homes for rent in Chicago are Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed and Clean, Private, Cozy Urban Oasis Chicago Greystone In Heart of Logan Square.

How many vacation rentals are there in Chicago?

With 935 Expedia vacation rentals, you're sure 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 Wrigley Field and Michigan Avenue.

What are vacation rentals like in Chicago?

Vacation rentals are private properties you can stay in for a short or long stay in Chicago. Vacation rentals provide amenities like WiFi and washers and dryers so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, vacation rentals can provide a sense of security away from public hotel elevators and busy front desks while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great option for a family trip or a small group gathering.