Indian Head Park Vacation Rentals

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Check prices for these dates

Tonight
Dec 4 - Dec 5
Tomorrow
Dec 5 - Dec 6
This weekend
Dec 5 - Dec 7
Next weekend
Dec 12 - Dec 14

Vacation Rentals in Indian Head Park

Indoor pool
Sentral Michigan Avenue

Sentral Michigan Avenue

4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (997)
"Loved my stay! Staff was amazing and the apartment had everything to make you feel like home. "
United States
Nicole
The price is ￥15,627
￥22,896 total
includes taxes & fees
Dec 7 - Dec 8
Sentral Michigan Avenue
Front of property - evening/night
Level Chicago – Old Town

Level Chicago – Old Town

4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (393)
"Clean room cool staff enjoyed my stay will come stay again. "
United States
Donald
Level Chicago – Old Town
49-inch Smart TV with digital channels, TV, streaming services
Kasa Magnificent Mile Chicago

Kasa Magnificent Mile Chicago

4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (642)
"Clean facilities, great staff, good location "
United States
Emily
Kasa Magnificent Mile Chicago
Deluxe Apartment, 1 Bedroom, Non Smoking, Balcony (Self Check-in with Virtual Front Desk) | Balcony
Kasa South Loop Chicago

Kasa South Loop Chicago

4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (380)
"A very clean and spacious apartment with a great view. The parking garage right next to the building is very convenient. If the water pressure be improved, that will be perfect."
United States
Tammy
Kasa South Loop Chicago
Property entrance
The Neighborhood Hotel-Little Italy

The Neighborhood Hotel-Little Italy

4.0 star property
Near West Side
9.6 out of 10, Exceptional, (221)
"Staff was courteous. Great location."
United States
Pamela
The Neighborhood Hotel-Little Italy
Free WiFi, bed sheets
Chicago luxury home suites

Chicago luxury home suites

2.0 star property
Downtown Chicago
10.0 out of 10, Exceptional, (2)
"Great service and communication throughout my entire stay. Very clean and easy to access to everything that i needed. Even though it was a short stay but had a comfortable and pleasant stay. Everything was available for me before i arrived. Thank you really. Great job."
Canada
pouya
The price is ￥20,414
￥23,962 total
includes taxes & fees
Dec 7 - Dec 8
Chicago luxury home suites
Living area
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 ￥13,120
￥15,403 total
includes taxes & fees
Dec 9 - Dec 10
Wrigleyville Suites
Business center
Kasa River North Chicago

Kasa River North Chicago

4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (180)
"Awesome stay "
United States
Sally
Kasa River North Chicago
1 bedroom, iron/ironing board, WiFi, bed sheets
Clean & Equipped 1BR Apt

Clean & Equipped 1BR Apt

Lakeview
9.0 out of 10, Wonderful, (38)
"Perfect for our needs, clean, convenient and great value. "
United States
Lisa B.
The price is ￥9,305
￥25,582 total
includes taxes & fees
Dec 8 - Dec 9
Clean & Equipped 1BR Apt
Comfort Double Room | Desk, laptop workspace, blackout drapes, free WiFi
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
3.8 out of 10, (67)
"Good "
United States
Abel
The price is ￥12,066
￥13,633 total
includes taxes & fees
Dec 5 - Dec 6
Comfort Inn Chicago Southland I-80 & I-294 Near Casino
Terrace/patio
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
Classic Apartment | Private kitchen
Stylish Apartment near Chicago Downtown

Stylish Apartment near Chicago Downtown

2.0 star property
Bridgeport
The price is ￥37,650
￥60,218 total
includes taxes & fees
Dec 7 - Dec 8
Stylish Apartment near Chicago Downtown
Microwave, oven, stovetop, coffee/tea maker
Cozy Studio in Hyde Park-Walk to Lake & University

Cozy Studio in Hyde Park-Walk to Lake & University

Hyde Park
8.8 out of 10, Excellent, (15)
"This place was nice and clean and close to what I needed to do. I appreciated that it was affordable. "
United States
Nancy
The price is ￥9,305
￥24,031 total
includes taxes & fees
Dec 7 - Dec 8
Cozy Studio in Hyde Park-Walk to Lake & University
Fridge, microwave, oven, stovetop
Lakeview 2BR Apartment

Lakeview 2BR Apartment

Lakeview
9.2 out of 10, Wonderful, (27)
"The apartment was as described and the customer service was amazing! "
United States
Michael M.
The price is ￥9,305
￥28,102 total
includes taxes & fees
Dec 8 - Dec 9
Lakeview 2BR Apartment
Interior
Art Villa

Art Villa

5.0 star property
West Town
10.0 out of 10, Exceptional, (2)
" "
United States
tomonobu
Art Villa
Fridge, microwave, oven, stovetop
Stylish 1BR in West Loop

Stylish 1BR in West Loop

Downtown Chicago
10.0 out of 10, Exceptional, (10)
"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"
United States
Jacob D.
The price is ￥9,770
￥26,128 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Stylish 1BR in West Loop
Outdoor dining
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, (269)
"Beautiful property fully loaded with amenities."
United States
Allie P.
3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place
Interior
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)
"Host was easy to communicate with and very thoughtful. We were in town for a concert and they gifted us with ear protection for us all. Location was great too "
United States
Tiffany N.
The price is ￥9,615
￥28,273 total
includes taxes & fees
Dec 7 - Dec 8
Twice as Nice: Chic 2BR Stay with Style & Space
Fridge, microwave, oven, stovetop
LakeHouse

LakeHouse

South Shore
9.4 out of 10, Exceptional, (24)
"This was a cute place with a lot of space. Nice backyard with areas to chill. The grand piano is beautiful and in tune!"
United States
Kenna C.
LakeHouse
Terrace/patio
Chicago Luxury Penthouse Gold Coast Best Location

Chicago Luxury Penthouse Gold Coast Best Location

Downtown Chicago
10.0 out of 10, Exceptional, (3)
"I used to live in Chicago and have a short term rental in Ohio myself. This place is legit. This property is in the best location close to beach restaurants and bars. Perfect for college reunion. Rooftop was awesome place for us to catch up over coffee and plan the day. The kitchen has everything we needed. Speakers throughout was a nice touch. I can’t be more complementary of the hosts responsiveness and helpfulness. We would definitely stay here again."
United States
Justin F.
Chicago Luxury Penthouse Gold Coast Best Location
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 Indian Head Park Hotel Reviews

Congress Plaza Hotel

Congress Plaza Hotel

10/10 Excellent
"Great"
Valentina 1-night trip
Posted 5 hours ago
Congress Plaza Hotel

Find out more about Indian Head Park

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

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Frequently asked questions

Can I find a vacation rental in Indian Head Park?

Yes, we offer vacation rentals near well known sights in Indian Head Park, or you can go with a more remote option if you want a relaxing place to stay. Indian Head Park is known for its shopping and restaurants.

What are some of the best vacation home rentals that Indian Head Park has to offer?

LakeHouse: Visitors like this Indian Head Park vacation home rental. It is located on the beach and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

What’s there to see and do in Indian Head Park?

While exploring the area, visit family-friendly sights like Galloping Ghost, or get outside and enjoy nature at Millennium Park. In the larger area, you’ll find popular places like United Center and Soldier Field.

What’s a vacation rental in Indian Head Park like?

A vacation rental is a private property where you can stay for a long or short time in Indian Head Park. Vacation rentals feature extras like laundry facilities and kitchens to help you enjoy your stay. If you're concerned about cleanliness, a vacation rental can offer a sense of safety away from public hotel elevators and busy lobbies while still allowing you to 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 an attractive option for families.