Photo by Ed Sochacki

Willow Springs Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Willow Springs vacation rentals

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1011)
"This place made a great landing spot for a holiday weekend w family. Clean, great location, loved the holiday decorations and indoor pool / outside hot tub. Will stay again! "
United States
Deidre
The price is ¥18,288
¥26,009 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Sentral Michigan Avenue

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (401)
"Great location, clean room and friendly staff!"
United States
Scott
Level Chicago – Old Town

Kasa Magnificent Mile Chicago

Kasa Magnificent Mile Chicago
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (650)
"Great location and place "
United States
Robert
Kasa Magnificent Mile Chicago

Kasa South Loop Chicago

Kasa South Loop Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (390)
"Would certainly stay again. The business center was an unexpected bonus, along with the great view. "
Canada
Mark
Kasa South Loop Chicago

Chicago luxury home suites

Chicago luxury home suites
2.0 star property
Downtown Chicago
7.4 out of 10, Good, (3)
"Do not book. This is a scam you will be asking to zelle a several hundred dollar security deposit after paying in full and before check in. You’ll receive sketchy FaceTime audio calls and messages from several different numbers requesting this. "
United States
Brooke
The price is ¥25,803
¥30,291 total
includes taxes & fees
Dec 20 - Dec 21
Chicago luxury home suites

The Neighborhood Hotel-Little Italy

The Neighborhood Hotel-Little Italy
4.0 star property
Near West Side
9.6 out of 10, Exceptional, (225)
"great place- excellent rooms and near tons of dining "
United States
chris
The Neighborhood Hotel-Little Italy

Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
9.6 out of 10, Exceptional, (26)
"Excellent location and very clean! Would stay again!"
United States
Jacob
The price is ¥19,734
¥23,166 total
includes taxes & fees
Dec 19 - Dec 20
Wrigleyville Suites

Kasa River North Chicago

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

Clean & Equipped 1BR Apt

Clean & Equipped 1BR Apt
Lakeview
9.0 out of 10, Wonderful, (41)
"Great location, apartment was clean, staff was very helpful."
United States
Steve H.
The price is ¥9,331
¥25,653 total
includes taxes & fees
Dec 21 - Dec 22
Clean & Equipped 1BR Apt

Comfort Inn Chicago Southland I-80 & I-294 Near Casino

Comfort Inn Chicago Southland I-80 & I-294 Near Casino
3.0 star property
Harvey
4.0 out of 10, (68)
"Good "
United States
Abel
The price is ¥11,833
¥13,368 total
includes taxes & fees
Dec 22 - Dec 23
Comfort Inn Chicago Southland I-80 & I-294 Near Casino

NEW LUXURY PENTHOUSE CONDO

NEW LUXURY PENTHOUSE CONDO
West Town
10.0 out of 10, Exceptional, (200)
"Great house with a great rooftop. "
United States
Francisco
NEW LUXURY PENTHOUSE CONDO

Lakeview 2BR Apartment

Lakeview 2BR Apartment
Lakeview
9.2 out of 10, Wonderful, (27)
"Great place and area!"
United States
Thomas J.
The price is ¥9,331
¥27,986 total
includes taxes & fees
Dec 21 - Dec 22
Lakeview 2BR Apartment

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

Twice as Nice: Chic 2BR Stay with Style & Space
Downtown Chicago
9.6 out of 10, Exceptional, (14)
"The neighborhood was so clean and quiet. Friendly neighbors. Perfect location, not far from everything downtown. "
United States
Shederia P.
The price is ¥12,227
¥31,298 total
includes taxes & fees
Dec 21 - Dec 22
Twice as Nice: Chic 2BR Stay with Style & Space

Stylish Apartment near Chicago Downtown

Stylish Apartment near Chicago Downtown
2.0 star property
Bridgeport
Stylish Apartment near Chicago Downtown

3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place

3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place
Near West Side
10.0 out of 10, Exceptional, (270)
"Wonderful place, great location! Communication was easy and everything met and exceeded our expectations."
United States
Kathleen N.
3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place

Modern West Loop Gem-City Views & Prime Location 6

Modern West Loop Gem-City Views & Prime Location 6
2.0 star property
Downtown Chicago
10.0 out of 10, Exceptional, (7)
"Great place. Very comfortable & really nice location- loved the corner coffee shop "
United States
Sandra
Modern West Loop Gem-City Views & Prime Location 6

Art Villa

Art Villa
5.0 star property
West Town
10.0 out of 10, Exceptional, (2)
Art Villa

55-56 Mag Mile Penthouse

55-56 Mag Mile Penthouse
Downtown Chicago
10.0 out of 10, Exceptional, (300)
"Great location, great property, great views. "
United States
Mark D.
55-56 Mag Mile Penthouse

Urban Farm Fun with Goats 10 Minutes To Downtown!

Urban Farm Fun with Goats 10 Minutes To Downtown!
East Garfield Park
7.8 out of 10, Good, (9)
"Great space, inside and out. Very kind friendly hosts. This was an amazing experience and we are grateful to Nicky and Drew for being so welcoming. "
United States
Jamie A.
Urban Farm Fun with Goats 10 Minutes To Downtown!

Charming 2-bedroom apartment in marvelous Blue Island with WiFi

Charming 2-bedroom apartment in marvelous Blue Island with WiFi
Blue Island
7.6 out of 10, Good, (4)
"Only issue was the water pressure in the bathroom was very very low. "
United States
Derrick M.
The price is ¥22,844
¥52,752 total
includes taxes & fees
Dec 19 - Dec 20
Charming 2-bedroom apartment in marvelous Blue Island with WiFi
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Willow Springs Hotel Reviews

Find out more about Willow Springs

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

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

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

Frequently asked questions

Can I find vacation rentals in Willow Springs?

Yes, you can find vacation rentals near well known local attractions in Willow Springs, or you can choose a more remote option if you're looking for relaxation. Willow Springs is known for its shopping and restaurants.

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

Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars: Visitors like this Willow Springs vacation home rental. It is located on a lake and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a private yard and a selection of games.

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 favorite places to visit like Michigan Avenue and United Center in the larger area.

What’s a vacation rental in Willow Springs like?

Vacation rentals are privately owned accommodations you can book for several days or longer in Willow Springs. Vacation rentals feature amenities such as laundry facilities and kitchens so you'll have all the conveniences of home. If you're concerned about a clean environment, a vacation rental can provide a sense of privacy away from public hotel elevators and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive option for family trips.