Search Holiday Rentals in Historic Route 66

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Top Holiday Rentals in Historic Route 66

Sentral Michigan Avenue
Interior
Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (417)
"Great location for museum campus area!!!"
The price is ₹15,646
₹20,810 total
includes taxes & fees
16 Jun - 17 Jun
Sentral Michigan Avenue
Sonder Market Hall
Interior
Sonder Market Hall
3.5 star property
8.4 out of 10, Very good, (88)
"Really pleased with my stay at the Market Hall. The process was extremely easy to reserve and access the room. The room was better than expected. I would definitely stay here again. Thanks Sonder!! "
The price is ₹11,296
₹13,262 total
includes taxes & fees
16 Jun - 17 Jun
Sonder Market Hall
Sonder South Wabash
City view from property
Sonder South Wabash
3.5 star property
8.8 out of 10, Excellent, (302)
"Everything was great!"
The price is ₹16,137
₹18,945 total
includes taxes & fees
5 Jun - 6 Jun
Sonder South Wabash
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Kasa Magnificent Mile Chicago
49-inch Smart TV with digital channels, TV, streaming services
Kasa Magnificent Mile Chicago
4.0 star property
9.2 out of 10, Wonderful, (243)
"Host was easily accessible. We had a relaxing stay and the apartment is very comfortable as well as clean. Definitely will stay here again."
The price is ₹21,706
₹33,881 total
includes taxes & fees
7 Jun - 8 Jun
Kasa Magnificent Mile Chicago
Junipine Resort
Terrace/patio
Junipine Resort
3.5 star property
9.2 out of 10, Wonderful, (1799)
"Enjoy Sedona's beautiful scenery up close during our stay at the Junipine Resort."
The price is ₹16,836
₹19,176 total
includes taxes & fees
5 Jun - 6 Jun
Junipine Resort
Level Chicago – Old Town
Front of property – evening/night
Level Chicago – Old Town
4.0 star property
8.8 out of 10, Excellent, (209)
"Nice"
The price is ₹32,251
₹39,277 total
includes taxes & fees
4 Jun - 5 Jun
Level Chicago – Old Town
Grand Canyon RV Glamping
Superior Loft | Private kitchen | Full-sized fridge, microwave, oven, stovetop
Grand Canyon RV Glamping
1.5 star property
9.0 out of 10, Wonderful, (429)
"Overall great experience! Just wish if the hot water in the shower could run for more than 10 minutes each time."
The price is ₹5,311
₹12,636 total
includes taxes & fees
2 Jun - 3 Jun
Grand Canyon RV Glamping
Found Chicago powered by Sonder
Interior
Found Chicago powered by Sonder
3.5 star property
7.6 out of 10, Good, (130)
"I enjoyed the fact that everything was close. The hotel was cleaned but I never saw a personal member. The code to enter didn't work and people inside had to help fellow clients to enter."
The price is ₹15,530
₹18,232 total
includes taxes & fees
27 Jun - 28 Jun
Found Chicago powered by Sonder
Sonder The Burnham
Exterior
Sonder The Burnham
3.5 star property
9.0 out of 10, Wonderful, (65)
" Cozy "
The price is ₹19,671
₹23,093 total
includes taxes & fees
12 Jun - 13 Jun
Sonder The Burnham
The Neighborhood Hotel-Little Italy
50-inch Smart TV with satellite channels
The Neighborhood Hotel-Little Italy
2.0 star property
10.0 out of 10, Exceptional, (33)
"Great property, very clean, staff was only a message away and very friendly. Definitely recommend and would stay again. "
The Neighborhood Hotel-Little Italy
Village Camp Flagstaff
Lobby sitting area
Village Camp Flagstaff
2.0 star property
9.4 out of 10, Exceptional, (56)
"Andrew, Sabrina were very attentive staff. Made us feel right at home, pleasant attitudes and great service! We arrived later evening Friday and our water was not working. We called and got after hours who was polite and sent maintenance straight over. Josh arrived and instantly fixed the problem and even circled back around to make sure we had hot water. Would definitely come back just to visit the atmosphere and staff. "
Village Camp Flagstaff
Kasa River North Chicago
Exterior
Kasa River North Chicago
4.0 star property
9.6 out of 10, Exceptional, (67)
"The building was clean and attractive. Security on site. Breakfast options close by. All the best sites walking distance. Units was amazing. Kasa very engaged and accessible. River Walk, boat excursions etc. Tours etc. Right there. Rooftop pool and all amenities on site wow!"
Kasa River North Chicago
Sonder Jewelers Row
Exterior
Sonder Jewelers Row
3.5 star property
8.2 out of 10, Very good, (104)
"Loved it "
The price is ₹18,377
₹21,575 total
includes taxes & fees
18 Jun - 19 Jun
Sonder Jewelers Row
WoodSpring Suites Chicago Addison
1 bedroom, premium bedding, pillow-top beds, desk
WoodSpring Suites Chicago Addison
2.5 star property
6.0 out of 10, (184)
"ITS A VERY NICE AND UPBEAT ESTABLISHMENT.......I ENJOYED THE STAY ONLY THING I DIDNT LIKE WAS THERE HOUSE KEEPING SCHEDULE BUT OTHER THAN THAT ITS A NICE QUIET LOCATION WITH NICE PEOPLE"
The price is ₹7,485
₹7,935 total
includes taxes & fees
30 May - 31 May
WoodSpring Suites Chicago Addison
Fort Marcy Hotel Suites by All Seasons Resort Lodging
2-Bedroom Condominium | Private kitchen | Fridge, microwave, oven, stovetop
Fort Marcy Hotel Suites by All Seasons Resort Lodging
3.0 star property
8.8 out of 10, Excellent, (2122)
"The unit was right across the street from the White Cross of the Martyrs monument and the trail from there down to town below. The view from the unit was spectacular! The unit itself was okay - fine for our needs and what we wanted in a unit, but nevertheless is a bit run down - water stains on a wall, average facilities, construction next door. "
The price is ₹14,732
₹21,520 total
includes taxes & fees
30 May - 31 May
Fort Marcy Hotel Suites by All Seasons Resort Lodging
White House at Grand Central
Comfort Apartment | Individually decorated, individually furnished, desk, laptop workspace
White House at Grand Central
3.0 star property
9.0 out of 10, Wonderful, (71)
"Great and stay nice and quiet, clean comfortable will book again soon"
The price is ₹5,870
₹16,783 total
includes taxes & fees
6 Jun - 7 Jun
White House at Grand Central
Arbor Suites at the Mall
Premium bedding, blackout curtains, iron/ironing board, free WiFi
Arbor Suites at the Mall
2.0 star property
7.4 out of 10, Good, (2121)
"This was an amazing property!! So clean and fresh and it felt like a being in an apartment. It sleeps at least 4 adults 2 kids. (We had the two king beds and the pullout couch) plus it had a full sized refrigerator and a stove and dishwasher!! Separate bathrooms between the upstairs bedroom and the downstairs bedroom made it nice too. Plus the blackout curtains were great!! 10/10!!!"
The price is ₹7,786
₹8,859 total
includes taxes & fees
30 May - 31 May
Arbor Suites at the Mall
Historic, Renovated Fire Station Vacation Rental!
Interior
Historic, Renovated Fire Station Vacation Rental!
3.5 star property
Historic, Renovated Fire Station Vacation Rental!
Kasa South Loop Chicago
Family Apartment, 3 Bedrooms, Non Smoking, Balcony | Living area | Smart TV, streaming services
Kasa South Loop Chicago
4.0 star property
9.4 out of 10, Exceptional, (161)
"Highly recommend! Amazing view of the city and the lake, clean and quiet yet close to everything. Thoughtfully furnished with nice surprises like power strips, white noise machine in bedroom, electric kettle etc. It was ideal and we’d stay there again. "
Kasa South Loop Chicago
Sonder The Plymouth
City view from property
Sonder The Plymouth
3.5 star property
8.4 out of 10, Very good, (67)
"Great place to stay and visit Chicago on foot. The property was exactly what we hoped for. "
The price is ₹17,743
₹20,831 total
includes taxes & fees
19 Jun - 20 Jun
Sonder The Plymouth
Don't see what you're looking for?
See all available properties in Historic Route 66
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.

Other types of properties in Historic Route 66 you may be interested in

Club Quarters Hotel, Central Loop, Chicago
Exterior
Club Quarters Hotel, Central Loop, Chicago
4.0 star property
8.6 out of 10, Excellent, (3063)
"Great"
The price is ₹13,438
₹15,776 total
includes taxes & fees
16 Jun - 17 Jun
Club Quarters Hotel, Central Loop, Chicago
Central Loop Hotel
Exterior
Central Loop Hotel
4.0 star property
8.6 out of 10, Excellent, (1617)
"Nice restaurant downstairs, great location, safe and walkable. Rooms are on the smaller side but clean with nice staff. The only issue is the room temperature for an older hotel, warmer then was comfortable. Wifi was good."
The price is ₹13,438
₹15,776 total
includes taxes & fees
16 Jun - 17 Jun
Central Loop Hotel
The Aquarius Casino Resort, BW Premier Collection
Outdoor pool
The Aquarius Casino Resort, BW Premier Collection
3.5 star property
8.0 out of 10, Very good, (5873)
"good"
The price is ₹4,076
₹6,551 total
includes taxes & fees
2 Jun - 3 Jun
The Aquarius Casino Resort, BW Premier Collection
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.

Holiday Rentals in Historic Route 66

Search for holiday rentals in Historic Route 66 on Expedia.co.uk! You can easily find your home rentals, villas, holiday apartments in Historic Route 66 using one of the methods below:

  • View our selection of featured holiday rentals in Historic Route 66
  • Use the map to find apartments and other holiday homes in the Historic Route 66 neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Historic Route 66 while they last

Look no further and take a look at our great range of rental properties in Historic Route 66!

Recent reviews of Historic Route 66 properties
Expedia verified reviews

Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

5/5 Excellent
"Location is excellent and walkable. Parking is expensive at $79 a night however so is parking everywhere in Chicago. Walls are pretty thin, you can hear a lot through them. Continental breakfast and complimentary cocktails in the evening were great. Rooms and property are all very clean and well maintained. Would stay again "
A verified traveller stayed at Embassy Suites by Hilton Chicago Downtown River North
Posted 17 hours ago
Embassy Suites by Hilton Chicago Downtown River North