Historic Route 66 Vacation Rentals

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Vacation Rentals in Historic Route 66

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (846)
"We would stay here again. Very happy with our stay "
The price is P9,741
P13,124 total
includes taxes & fees
Aug 4 - Aug 5
Sentral Michigan Avenue

Junipine Resort

3.5 star property
9.2 out of 10, Wonderful, (2150)
"Great place"
The price is P8,323
P9,564 total
includes taxes & fees
Aug 11 - Aug 12
Junipine Resort

Sonder by Marriott Bonvoy Market Hall Apartments West Loop

3.5 star property
8.2 out of 10, Very Good, (335)
"The property canceled on us 4 hours prior to check in"
The price is P7,293
P8,561 total
includes taxes & fees
Aug 17 - Aug 18
Sonder by Marriott Bonvoy Market Hall Apartments West Loop

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (332)
"Finding a park is hard and the process of getting a room is very tedious but still very beautiful I’ve been twice "
Level Chicago – Old Town

Sonder by Marriott Bonvoy South Wabash Apartments South Loop

3.5 star property
8.8 out of 10, Excellent, (593)
"I would stay again. "
The price is P8,664
P10,170 total
includes taxes & fees
Aug 25 - Aug 26
Sonder by Marriott Bonvoy South Wabash Apartments South Loop

Kasa Magnificent Mile Chicago

4.0 star property
9.4 out of 10, Exceptional, (453)
"Nice views and convenient location to transit and dining"
Kasa Magnificent Mile Chicago

Sonder by Marriott Bonvoy The Plymouth Apartments Loop

3.5 star property
7.8 out of 10, Good, (124)
"Super convenient location. Lots of parking options and able to walk to all sites in this area."
The price is P7,538
P8,849 total
includes taxes & fees
Aug 25 - Aug 26
Sonder by Marriott Bonvoy The Plymouth Apartments Loop

Kasa South Loop Chicago

4.0 star property
9.4 out of 10, Exceptional, (323)
"Great stay"
Kasa South Loop Chicago

Sonder by Marriott Bonvoy The Burnham Apartments Loop

3.5 star property
9.0 out of 10, Wonderful, (200)
"Clean, new, spacious "
The price is P12,139
P14,250 total
includes taxes & fees
Aug 24 - Aug 25
Sonder by Marriott Bonvoy The Burnham Apartments Loop

Fort Marcy Hotel Suites by All Seasons Resort Lodging

3.0 star property
8.8 out of 10, Excellent, (2192)
"Great location to activities in the area. We would stay here again. "
The price is P6,815
P11,489 total
includes taxes & fees
Aug 12 - Aug 13
Fort Marcy Hotel Suites by All Seasons Resort Lodging

The Gem Museum Suites

3.5 star property
9.4 out of 10, Exceptional, (80)
"Had a good and comfortable stay "
The price is P11,868
P13,587 total
includes taxes & fees
Aug 12 - Aug 13
The Gem Museum Suites

The Neighborhood Hotel-Little Italy

4.0 star property
9.8 out of 10, Exceptional, (181)
"Great suite"
The Neighborhood Hotel-Little Italy

Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

3.5 star property
8.2 out of 10, Very Good, (169)
"Great location. Clean (very clean) and comfortable apartments with everything you need. Cons: soundproofing from the city center is weak, all sounds are heard quite well. In terms of price per room ratio - a super option. I will book next time, and I recommend it to everyone."
The price is P9,251
P10,860 total
includes taxes & fees
Aug 17 - Aug 18
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

Grand Canyon RV Glamping

1.5 star property
9.0 out of 10, Wonderful, (564)
"Love staying at this property. "
The price is P5,760
P6,791 total
includes taxes & fees
Aug 3 - Aug 4
Grand Canyon RV Glamping

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

2.5 star property
3.6 out of 10, (50)
"Property is advertised as a Comfort Inn, but is actually undergoing the transformation of becoming a Comfort Inn. It is still very much so operating as a motel on the south side of Chicago. Be safe. "
The price is P4,852
P5,481 total
includes taxes & fees
Aug 4 - Aug 5
Comfort Inn Chicago Southland I-80 & I-294 Near Casino

Wrigleyville Suites

2.0 star property
10.0 out of 10, Exceptional, (11)
"Excellent location and very clean! Would stay again!"
Wrigleyville Suites

Kasa River North Chicago

4.0 star property
9.6 out of 10, Exceptional, (157)
"Great location and very clean! Will definitely be staying again. "
Kasa River North Chicago

Sonder by Marriott Bonvoy The Opal Apartments River North

3.5 star property
8.6 out of 10, Excellent, (43)
"Great location. Apartment had all the amenities needed. Felt safe. Only not so good part was that being in downtown, it wasn't super quiet at times. Would stay here again without a doubt."
The price is P8,223
P9,653 total
includes taxes & fees
Aug 17 - Aug 18
Sonder by Marriott Bonvoy The Opal Apartments River North

Arizona Mountain Inn and Cabins

3.0 star property
8.4 out of 10, Very Good, (239)
"Unique property in the woods , staff were great and breakfast was awesome "
The price is P9,394
P10,444 total
includes taxes & fees
Aug 3 - Aug 4
Arizona Mountain Inn and Cabins

All Towne Suites

2.0 star property
9.2 out of 10, Wonderful, (249)
"Great stay, lovely family owned property "
The price is P4,094
P4,595 total
includes taxes & fees
Aug 2 - Aug 3
All Towne 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 Historic Route 66 Hotel Reviews