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Willow Springs Holiday Rentals

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Our top choices for Willow Springs holiday rentals

Holiday Home in Willow Springs

Coziest estate home 20 minutes to downtown
8.8 out of 10, Excellent, (16)
"We liked the home, it had everything we needed. We loved having the pool table to play on, that was a hit! The backyard was clean and large, with lots of room! We had the privacy that we needed!"
United States
Gabriela N.
The price is NZ$685
includes taxes & fees
1 Jan - 2 Jan 2026
Coziest estate home 20 minutes to downtown

ENVITAE Hotel 4 Bedroom Luxury Apartments

ENVITAE Hotel 4 Bedroom Luxury Apartments
2.0 star property
10.0 out of 10, Exceptional, (8)
"We loved at our stay at this property. It was one of the best stays we have had on vacation."
United States
Javeria
The price is NZ$2,154
includes taxes & fees
5 Jan - 6 Jan 2026
ENVITAE Hotel 4 Bedroom Luxury Apartments

Aparthotel in Downtown Chicago

Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (1026)
"My favorite place to stay hands-down"
United States
Michele
The price is NZ$286
includes taxes & fees
13 Jan - 14 Jan 2026
Sentral Michigan Avenue

Aparthotel in Downtown Chicago

Chicago luxury home suites
2.0 star property
10.0 out of 10, Exceptional, (4)
"Amazing stay! The location is very central and close to everything. The room was spotless, and the mattress was very comfortable. I really appreciated that the property is pet friendly. I was able to bring my dog along, which made the trip even better. The view was absolutely stunning. The hosts were very responsive and helpful throughout our stay. Highly recommend!"
Canada
Alex
The price is NZ$266
includes taxes & fees
4 Jan - 5 Jan 2026
Chicago luxury home suites

Aparthotel in Downtown Chicago

Kasa River North Chicago
4.0 star property
9.6 out of 10, Exceptional, (182)
"Awesome stay "
United States
Sally
Kasa River North Chicago

Apartment in Downtown Chicago

1BR Modern Luxe Apt with In-Unit Laundry
10.0 out of 10, Exceptional, (1)
"Great experience for me and my wife I would definitely come back "
United States
ShowtimeFam1
The price is NZ$290
includes taxes & fees
1 Jan - 2 Jan 2026
1BR Modern Luxe Apt with In-Unit Laundry
9.8 out of 10, Exceptional, (16)
"The neighborhood was so clean and quiet. Friendly neighbors. Perfect location, not far from everything downtown. "
United States
Shederia P.
The price is NZ$328
includes taxes & fees
1 Jan - 2 Jan 2026
Twice as Nice: Chic 2BR Stay with Style & Space

Aparthotel in Downtown Chicago

Level Chicago – Old Town
4.0 star property
9.0 out of 10, Wonderful, (407)
"Great location, clean room and friendly staff!"
United States
Scott
Level Chicago – Old Town

Apartment in Downtown Chicago

Stylish 1BR in West Loop
10.0 out of 10, Exceptional, (10)
"Great host comfortable bed close to restaurants and parks"
United States
Alana C.
The price is NZ$290
includes taxes & fees
1 Jan - 2 Jan 2026
Stylish 1BR in West Loop

Apartment in Downtown Chicago

Gold Coast Living: Modern Studio Unit
10.0 out of 10, Exceptional, (5)
"The communication was really effective and made for a smooth check in and check out process. Host was friendly and made great recommendations, 10/10 would stay again!"
United States
Seynabou
The price is NZ$285
includes taxes & fees
4 Jan - 5 Jan 2026
Gold Coast Living: Modern Studio Unit

Apartment in Downtown Chicago

3BR Luxury Suite w/Gym and Balcony
2.0 star property
9.4 out of 10, Exceptional, (20)
"The apartment was clean and in an easily accessible location just a short walk to public transport. We stayed three nights on a business trip and would definitely stay again. "
United States
Ryan S.
The price is NZ$1,073
includes taxes & fees
3 Jan - 4 Jan 2026
3BR Luxury Suite w/Gym and Balcony

Apartment in Downtown Chicago

West Loop Living – Bright 1BR
10.0 out of 10, Exceptional, (6)
"Well-outfitted, nice apartment. Nearby (walkable) Jewel-Osco grocery, restaurants, and pay-parking. Moderate noise from nearby Chicago "L" Green Line."
United States
Jeffrey
The price is NZ$290
includes taxes & fees
4 Jan - 5 Jan 2026
West Loop Living – Bright 1BR

Apartment in Downtown Chicago

Sun-Drenched 1BR Apartment
10.0 out of 10, Exceptional, (2)
"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 NZ$290
includes taxes & fees
4 Jan - 5 Jan 2026
Sun-Drenched 1BR Apartment
2.0 star property
The price is NZ$290
includes taxes & fees
5 Jan - 6 Jan 2026
Chicago-Themed 1BR in a Central Spot near Downtown
9.6 out of 10, Exceptional, (4)
"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 NZ$541
includes taxes & fees
5 Jan - 6 Jan 2026
River North Rooftop With In and Out Parking 3

Apartment in Downtown Chicago

The One: A 1BR Stay That Feels Like Home
8.4 out of 10, Very good, (5)
"Very nice condo in a quiet neighborhood"
Canada
Patrick
The price is NZ$290
includes taxes & fees
7 Jan - 8 Jan 2026
The One: A 1BR Stay That Feels Like Home

Apartment in Downtown Chicago

Complete 1BR Home Sum
The price is NZ$290
includes taxes & fees
1 Jan - 2 Jan 2026
Complete 1BR Home Sum

Apartment in Downtown Chicago

Sleek 1BR Apt w/ Laundry
10.0 out of 10, Exceptional, (1)
"I was a little hesitant since I didn’t see any reviews, and was bit nervous. However, all that was put to rest when we arrived. Everything was as described and the photos were accurate. It was clean and minimalistic. Nice space for two for a week. Having the full kitchen was great. About 15 min walk to the brown line and 25 to the blue Line and not a lot of restaurants close by is about the only complaint. Bed could have been more comfortable too."
United States
Anonymous traveller
The price is NZ$290
includes taxes & fees
21 Jan - 22 Jan 2026
Sleek 1BR Apt w/ Laundry
2.0 star property
The price is NZ$328
includes taxes & fees
4 Jan - 5 Jan 2026
Stylish Japanese-Themed 2BR Apt Close to Downtown

Aparthotel in Lakeview

Wrigleyville Suites
2.0 star property
9.6 out of 10, Exceptional, (27)
"Nice place "
United States
Barry
The price is NZ$222
includes taxes & fees
6 Jan - 7 Jan 2026
Wrigleyville Suites
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 Willow Springs Hotel Reviews

Find out more about Willow Springs

Everything you need to know about Willow Springs 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 Willow Springs 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 Willow Springs holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Willow Springs holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Willow Springs. 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 Willow Springs 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 Willow Springs holiday rentals we have selected for you start as low as NZ$148 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Willow Springs rentals

At Expedia, we put the best Willow Springs 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 Willow Springs 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 Willow Springs 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 Willow Springs. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Willow Springs?

Yes, there are holiday rentals close to the most popular sights in Willow Springs, or you can select a more secluded option if you're looking for a relaxing stay. Willow Springs is known for its shopping and restaurants.

What are some of the best holiday rentals that Willow Springs has to offer?

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed: This holiday home rental outside of Willow Springs offers a patio, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop and a microwave.

What’s there to see and do in Willow Springs?

Explore the area and family-friendly sights such as Galloping Ghost, or get out into nature at a spot like Millennium Park. You’ll find favourite places to visit such as Michigan Avenue and United Center in the wider area.

What’s a holiday rental in Willow Springs like?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Willow Springs. Holiday rentals offer amenities such as laundry facilities and kitchens so you'll have everything you want. If you're concerned about a clean environment, holiday rentals can offer a sense of safety away from public hotel lifts and busy reception areas while still allowing you to travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular choice for a family getaway.