A dirt path flanked by leafless trees, leading towards a distant building.

Willow Springs Vacation Rentals

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Check prices for these dates

In two weeks
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

Our top choices for Willow Springs vacation rentals

Indoor pool

1. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,240 reviews)
"Great property and location."
United States
Michael
The price is AED 585
AED 794 total
includes taxes & fees
30 Aug - 31 Aug
Sentral Michigan Avenue
Coffee/tea maker, fridge, microwave, oven

2. *The Comfy King Ranch*King Bed Suite*Fast Wi-Fi

*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
Worth
9.4 out of 10, Exceptional, (63 reviews)
"Checking in was easy, the place is as advertised, communication was easy as well, had no problems, will be staying there again. "
United States
Joe M.
The price is AED 681
AED 1,454 total
includes taxes & fees
9 Aug - 10 Aug
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
Lake

3. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
7.6 out of 10, Good, (11 reviews)
"Great location and super clean!"
United States
Erica
The price is AED 904
AED 1,293 total
includes taxes & fees
8 Sep - 9 Sep
Kasa Lake Shore Chicago
Full-size fridge, microwave, oven, stovetop

4. Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (514 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 AED 865
AED 1,106 total
includes taxes & fees
31 Aug - 1 Sep
Level Chicago – Old Town
Property grounds

5. Spacious and Inviting

Spacious and Inviting
Willowbrook
10.0 out of 10, Exceptional, (1 review)
"I had family in from the West Coast. I would recommend. Very well decorated and very cozy. Nice outside deck with plenty of seating and large yard! It was great to be able to have family over and visit. Communication was very good also! Thank you! "
United States
karin e.
Spacious and Inviting
Coffee/tea maker, fridge, microwave, oven

6. PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!

PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!
Westchester
9.6 out of 10, Exceptional, (21 reviews)
"Great location and the place was immaculate. Host was very nice."
United States
Carl M.
The price is AED 717
AED 1,707 total
includes taxes & fees
10 Aug - 11 Aug
PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!
Apartment, Private Bathroom | Lounge

7. At Home in Oak Park

At Home in Oak Park
3.5 star property
Oak Park
9.6 out of 10, Exceptional, (11 reviews)
"Great place, clean, and very accommodating! "
United States
Theresa
The price is AED 735
AED 1,249 total
includes taxes & fees
23 Aug - 24 Aug
At Home in Oak Park
Coffee/tea maker, fridge, microwave, oven

8. River North Rooftop With In and Out Parking 5

River North Rooftop With In and Out Parking 5
Downtown Chicago
9.8 out of 10, Exceptional, (6 reviews)
"Everything was amazing, property was even better than expected"
United States
Jacob
The price is AED 1,087
AED 2,183 total
includes taxes & fees
16 Aug - 17 Aug
River North Rooftop With In and Out Parking 5
Smart TV, video games, foosball, table tennis

9. Sleeps 10 + Coffee bar + Game Room + Train to CHGO - Holiday Home

Sleeps 10 + Coffee bar + Game Room + Train to CHGO - Holiday Home
Brookfield
10.0 out of 10, Exceptional, (12 reviews)
"Wonderful place to stay!"
United States
Chasity D.
The price is AED 1,074
AED 2,891 total
includes taxes & fees
23 Aug - 24 Aug
Sleeps 10 + Coffee bar + Game Room + Train to CHGO - Holiday Home
TV, offices

10. 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, (8 reviews)
"Awesome location, great place would definitely recommend will hopefully return"
United States
lucas c.
The price is AED 1,091
AED 2,187 total
includes taxes & fees
10 Aug - 11 Aug
River North Rooftop With In and Out Parking 1
TV, offices

11. 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.
The price is AED 676
AED 911 total
includes taxes & fees
9 Aug - 10 Aug
LIVN Millennium Park Downtown Chicago Superior 1BR
1 bedroom, iron/ironing board, travel crib, WiFi

12. LIVN West Loop Chicago King Studio

LIVN West Loop Chicago King Studio
Downtown Chicago
10.0 out of 10, Exceptional, (5 reviews)
"Amazing studio apartment style room, super clean, very helpful staff, and great location."
United States
William
The price is AED 654
AED 881 total
includes taxes & fees
9 Aug - 10 Aug
LIVN West Loop Chicago King Studio
Coffee/tea maker, fridge, microwave, oven

13. Cozy, Comfortable and Convenient apartment. Close to everything!

Cozy, Comfortable and Convenient apartment. Close to everything!
Oak Park
9.8 out of 10, Exceptional, (77 reviews)
"The host responded quickly to my requests. Apartment was clean. Kitchen well stocked with cooking, utensils, spices, etc. He registered my car so I coiud park on the street without any problem. Close to the Blue Line stop to take the "L" into downtown Chicago."
United States
Michael
The price is AED 469
AED 1,189 total
includes taxes & fees
18 Aug - 19 Aug
Cozy, Comfortable and Convenient apartment. Close to everything!
3 bedrooms, iron/ironing board, WiFi, bed sheets

14. Plymouth Collection: 3BD 2BA High Floor with Gym

Plymouth Collection: 3BD 2BA High Floor with Gym
Downtown Chicago
10.0 out of 10, Exceptional, (3 reviews)
"The suite was excellent. Clean and very well furnished. The building is located within walking distance to many of the things that we did. We would stay in this place again in a heartbeat. Very pleased with our experience"
United States
Derek M.
The price is AED 966
AED 2,109 total
includes taxes & fees
11 Aug - 12 Aug
Plymouth Collection: 3BD 2BA High Floor with Gym
Dining

15. LUXE 3 BR, 2 BA + Hot Tub

LUXE 3 BR, 2 BA + Hot Tub
Elmhurst
8.8 out of 10, Excellent, (53 reviews)
"Hot tub was very nice!"
United States
Jeff
The price is AED 735
AED 1,446 total
includes taxes & fees
7 Sep - 8 Sep
LUXE 3 BR, 2 BA + Hot Tub
Interior

16. Vintage Urban Retreat

Vintage Urban Retreat
Oak Park
10.0 out of 10, Exceptional, (15 reviews)
"It was a very nice neighborhood, with many restaurants and retail establishments in proximity. We really enjoyed our stay and our host was an excellent when it comes to communication."
United States
Tim P.
The price is AED 973
AED 2,313 total
includes taxes & fees
12 Aug - 13 Aug
Vintage Urban Retreat
Exclusive Room, Private Bathroom, Garden View (2nd Floor) | Exterior

17. Historic Oak Park Residence

Historic Oak Park Residence
2.0 star property
Oak Park
9.6 out of 10, Exceptional, (12 reviews)
"The house is in an amazing neighborhood, easy access to subway, extremely clean and great follow-up and follow through communication with owner!"
United States
Ann-Marie
The price is AED 1,632
AED 2,276 total
includes taxes & fees
9 Aug - 10 Aug
Historic Oak Park Residence
Exterior

18. ✽ Charming Cottage ✽ close to College/Town/Station

✽ Charming Cottage ✽ close to College/Town/Station
Wheaton
10.0 out of 10, Exceptional, (70 reviews)
"This was the perfect place for our short stay!"
United States
Laurie R.
The price is AED 661
AED 1,183 total
includes taxes & fees
17 Aug - 18 Aug
✽ Charming Cottage ✽ close to College/Town/Station
Interior

19. Chic 3bed 2bath Home with free parking close to United Center

Chic 3bed 2bath Home with free parking close to United Center
Oak Park
9.8 out of 10, Exceptional, (19 reviews)
"Overall just great lovely area and chill place, rooms was great and I love the Roku tvs to sit back In chill!"
United States
Chantrice A.
The price is AED 826
AED 2,494 total
includes taxes & fees
9 Aug - 10 Aug
Chic 3bed 2bath Home with free parking close to United Center
Smart TV

20. Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Maywood
8.0 out of 10, Very Good, (31 reviews)
"Pros: Quiet neighborhood, felt safe going in and out of the house. Upstairs bathroom shower was amazing. Cons: warmer in living room, stained pillows, couches and floors felt like dust mites all over( simple fix) All in all it was a good stay."
United States
Amal
The price is AED 545
AED 1,106 total
includes taxes & fees
10 Aug - 11 Aug
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
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

Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago

8/10 Good
"Was fine for a two night stay. Probably wouldn’t have booked if I had known the bathroom door was see through though. Not everyone is staying alone or sharing a room with someone they are comfortable with seeing almost everything through the door. So would not book again."
Emma 2-night trip
Posted 1 hour ago
Club Quarters Hotel, Central Loop, Chicago

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?

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line: Visitors like this Willow Springs vacation home rental. It is located in the city center and has a balcony, a barbecue grill, 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 you can cook with friends or family.

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 Grant Park. You’ll find favorite places to visit like United Center and Soldier Field 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.