Northwest Chicago Holiday Rentals

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Holiday Rentals in Northwest Chicago

Barrington Meadows Wedding Venue & Farm: Where Dreams Come True

The price is AU$17,603
includes taxes & fees
6 Oct - 7 Oct
Barrington Meadows Wedding Venue & Farm: Where Dreams Come True

Sonder by Marriott Bonvoy Market Hall Apartments West Loop

3.5 star property
8.0 out of 10, Very good, (374)
"Great stay!"
The price is AU$225
includes taxes & fees
2 Nov - 3 Nov
Sonder by Marriott Bonvoy Market Hall Apartments West Loop

Sonder by Marriott Bonvoy The Burnham Apartments Loop

3.5 star property
8.8 out of 10, Excellent, (235)
"Great location and lovely amenities. "
The price is AU$255
includes taxes & fees
2 Nov - 3 Nov
Sonder by Marriott Bonvoy The Burnham Apartments Loop

The Neighborhood Hotel-Little Italy

4.0 star property
9.6 out of 10, Exceptional, (207)
"This place was perfect "
The Neighborhood Hotel-Little Italy

The Gem Museum Suites

3.5 star property
9.4 out of 10, Exceptional, (89)
"Super nice hotel and staff "
The price is AU$357
includes taxes & fees
28 Oct - 29 Oct
The Gem Museum Suites

Wrigleyville Suites

2.0 star property
9.6 out of 10, Exceptional, (19)
"Excellent location and very clean! Would stay again!"
The price is AU$188
includes taxes & fees
6 Oct - 7 Oct
Wrigleyville Suites

Stylish Apartment near Chicago Downtown

2.0 star property
The price is AU$514
includes taxes & fees
6 Oct - 7 Oct
Stylish Apartment near Chicago Downtown

Clean & Equipped 1BR Apt

9.4 out of 10, Exceptional, (25)
"Good experience. Would stay there again "
The price is AU$285
includes taxes & fees
3 Nov - 4 Nov
Clean & Equipped 1BR Apt

Art Villa

5.0 star property
10.0 out of 10, Exceptional, (2)
" "
The price is AU$954
includes taxes & fees
15 Oct - 16 Oct
Art Villa

Charming 2BR in Vibrant Lakeview

9.4 out of 10, Exceptional, (19)
"This place was great! Loved my stay!"
The price is AU$325
includes taxes & fees
6 Oct - 7 Oct
Charming 2BR in Vibrant Lakeview

Stylish 1BR in West Loop

10.0 out of 10, Exceptional, (5)
"We stayed for 4th of July weekend and had a wonderful time. Property is close to coffee shops, book stores, and within walking distance of nice restaurants. Easy paid parking nearby. The apartment was clean and everything we needed"
The price is AU$335
includes taxes & fees
15 Oct - 16 Oct
Stylish 1BR in West Loop

Relaxing Chicago Studio

10.0 out of 10, Exceptional, (17)
"Had a great stay. Great location. "
The price is AU$265
includes taxes & fees
4 Nov - 5 Nov
Relaxing Chicago Studio

Twice as Nice: Chic 2BR Stay with Style & Space

9.4 out of 10, Exceptional, (9)
"Had a very nice time in Chicago!"
The price is AU$376
includes taxes & fees
3 Nov - 4 Nov
Twice as Nice: Chic 2BR Stay with Style & Space

Sonder by Marriott Bonvoy Greektown Apartments

3.5 star property
8.6 out of 10, Excellent, (65)
"The kitchen had everything we needed, great space overall, safe location, clean, near everything we needed, access to bus and rail very close, we really enjoyed our stay. "
The price is AU$346
includes taxes & fees
2 Nov - 3 Nov
Sonder by Marriott Bonvoy Greektown Apartments

Bright & Modern Lakeview Studio

9.0 out of 10, Wonderful, (9)
"This is a great location to hit the Lakeview neighborhood with Wrigley Field just a couple blocks over. When trying to get the check-in instructions, there were a lot of hoops to jump through to get the payment to the management company for this property. I had to contact the host (management company) multiple times to get the links to the forms to upload a driver's license and selfie holding said driver's license. Another URL to get to the payment Venmo account. And another URL for the...
The price is AU$293
includes taxes & fees
3 Nov - 4 Nov
Bright & Modern Lakeview Studio

Lakeview 2BR Apartment

9.4 out of 10, Exceptional, (16)
"Great location, charming building. The photos in the listing are very accurate. Super close to the L and restaurants."
The price is AU$325
includes taxes & fees
4 Nov - 5 Nov
Lakeview 2BR Apartment

Ground Floor Studios in Chicago by 747 Lofts

2.0 star property
9.4 out of 10, Exceptional, (18)
"Its was in a good location for anyone who has family close by. Bed was wonderful. "
Ground Floor Studios in Chicago by 747 Lofts

Nice 1BR Spot, Unwind & Relax

10.0 out of 10, Exceptional, (17)
"This location was perfect for our nights in Chicago. We were within walking distance of great shopping and eating. "
The price is AU$276
includes taxes & fees
6 Oct - 7 Oct
Nice 1BR Spot, Unwind & Relax

Stylish 1BR in Lakeview Chicago

8.8 out of 10, Excellent, (18)
"Terrific overall stay. Great location and nice place. Highly recommend."
The price is AU$306
includes taxes & fees
3 Nov - 4 Nov
Stylish 1BR in Lakeview Chicago

Cozy studio in Andersonville Chicago

9.2 out of 10, Wonderful, (34)
"Great studio apartment. Needed just one night and worth the price. Would recommend."
The price is AU$246
includes taxes & fees
28 Oct - 29 Oct
Cozy studio in Andersonville Chicago
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 Northwest Chicago Hotel Reviews

Find out more about Northwest Chicago

Find out more about Northwest Chicago

Everything you need to know about Northwest 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 Northwest 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 Northwest Chicago holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Northwest Chicago holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Northwest 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Northwest 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 Northwest Chicago holiday rentals we have selected for you start as low as AU$188 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Northwest Chicago rentals

At Expedia, we put the best Northwest 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 Northwest 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 Northwest 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 Northwest 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.