Historic Route 66 Vacation Rentals

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Check prices for these dates

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Aug 12 - Aug 13
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Aug 13 - Aug 14
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Aug 15 - Aug 17
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Aug 22 - Aug 24

Vacation Rentals in Historic Route 66

Sentral Michigan Avenue
Interior

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (874)
"Great stay!"
The price is P9,654
P13,007 total
includes taxes & fees
Sep 2 - Sep 3
Sentral Michigan Avenue
Junipine Resort
Terrace/patio

Junipine Resort

3.5 star property
9.2 out of 10, Wonderful, (2163)
"Staff and natures beauty around hotel! "
The price is P10,387
P11,935 total
includes taxes & fees
Aug 24 - Aug 25
Junipine Resort
Sonder by Marriott Bonvoy Market Hall Apartments West Loop
1 bedroom, individually decorated, individually furnished, desk

Sonder by Marriott Bonvoy Market Hall Apartments West Loop

3.5 star property
8.2 out of 10, Very Good, (340)
"The property canceled on us 4 hours prior to check in"
The price is P7,225
P8,482 total
includes taxes & fees
Aug 25 - Aug 26
Sonder by Marriott Bonvoy Market Hall Apartments West Loop
Level Chicago – Old Town
Front of property - evening/night

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (337)
"A lot of good food options walkable distance. "
Level Chicago – Old Town
The Neighborhood Hotel-Little Italy
Front of property

The Neighborhood Hotel-Little Italy

4.0 star property
9.6 out of 10, Exceptional, (188)
"Property was extremely comfortable in a great area."
The Neighborhood Hotel-Little Italy
Kasa Magnificent Mile Chicago
49-inch Smart TV with digital channels, TV, streaming services

Kasa Magnificent Mile Chicago

4.0 star property
9.4 out of 10, Exceptional, (465)
"Great location and great property will stay again "
Kasa Magnificent Mile Chicago
Sonder by Marriott Bonvoy South Wabash Apartments South Loop
36-inch flat-screen TV with digital channels, TV

Sonder by Marriott Bonvoy South Wabash Apartments South Loop

3.5 star property
8.8 out of 10, Excellent, (611)
"I would stay again. "
The price is P6,258
P7,346 total
includes taxes & fees
Sep 4 - Sep 5
Sonder by Marriott Bonvoy South Wabash Apartments South Loop
Fort Marcy Hotel Suites by All Seasons Resort Lodging
Property grounds

Fort Marcy Hotel Suites by All Seasons Resort Lodging

3.0 star property
8.8 out of 10, Excellent, (2193)
"Great location to activities in the area. We would stay here again. "
The price is P6,780
P11,430 total
includes taxes & fees
Aug 24 - Aug 25
Fort Marcy Hotel Suites by All Seasons Resort Lodging
Kasa South Loop Chicago
Balcony

Kasa South Loop Chicago

4.0 star property
9.4 out of 10, Exceptional, (329)
"Great stay"
Kasa South Loop Chicago
Sonder by Marriott Bonvoy The Burnham Apartments Loop
Lobby

Sonder by Marriott Bonvoy The Burnham Apartments Loop

3.5 star property
9.0 out of 10, Wonderful, (203)
"Clean, new, spacious "
The price is P8,500
P9,979 total
includes taxes & fees
Aug 17 - Aug 18
Sonder by Marriott Bonvoy The Burnham Apartments Loop
The Gem Museum Suites
Private kitchen

The Gem Museum Suites

3.5 star property
9.4 out of 10, Exceptional, (83)
"Super nice hotel and staff "
The price is P12,584
P14,407 total
includes taxes & fees
Sep 2 - Sep 3
The Gem Museum Suites
Sonder by Marriott Bonvoy The Plymouth Apartments Loop
Property amenity

Sonder by Marriott Bonvoy The Plymouth Apartments Loop

3.5 star property
7.8 out of 10, Good, (129)
"Super convenient location. Lots of parking options and able to walk to all sites in this area."
The price is P6,013
P7,059 total
includes taxes & fees
Aug 25 - Aug 26
Sonder by Marriott Bonvoy The Plymouth Apartments Loop
Grand Canyon RV Glamping
Private kitchen

Grand Canyon RV Glamping

1.5 star property
9.0 out of 10, Wonderful, (572)
"Love staying at this property. "
The price is P4,760
P5,612 total
includes taxes & fees
Aug 25 - Aug 26
Grand Canyon RV Glamping
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
50-inch flat-screen TV with digital channels, TV

Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

3.5 star property
8.2 out of 10, Very Good, (171)
"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 P7,713
P9,055 total
includes taxes & fees
Sep 1 - Sep 2
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
Wrigleyville Suites
Living area

Wrigleyville Suites

2.0 star property
9.6 out of 10, Exceptional, (13)
"Excellent location and very clean! Would stay again!"
The price is P4,161
P7,738 total
includes taxes & fees
Aug 14 - Aug 15
Wrigleyville Suites
All Towne Suites
Exterior

All Towne Suites

2.0 star property
9.2 out of 10, Wonderful, (257)
"Friendly staff, clean room, and comfortable bed."
The price is P4,621
P5,186 total
includes taxes & fees
Aug 18 - Aug 19
All Towne Suites
Kasa River North Chicago
Business center

Kasa River North Chicago

4.0 star property
9.6 out of 10, Exceptional, (161)
"Great location and very clean! Will definitely be staying again. "
Kasa River North Chicago
Arizona Mountain Inn and Cabins
Iron/ironing board, bed sheets

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 P9,345
P10,389 total
includes taxes & fees
Aug 15 - Aug 16
Arizona Mountain Inn and Cabins
Sonder by Marriott Bonvoy The Opal Apartments River North
1 bedroom, individually furnished, desk, iron/ironing board

Sonder by Marriott Bonvoy The Opal Apartments River North

3.5 star property
8.4 out of 10, Very Good, (46)
"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 P7,713
P9,055 total
includes taxes & fees
Sep 3 - Sep 4
Sonder by Marriott Bonvoy The Opal Apartments River North
Comfort Inn Chicago Southland I-80 & I-294 Near Casino
1 bedroom, desk, laptop workspace, blackout drapes

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

2.5 star property
3.6 out of 10, (51)
"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 P4,826
P5,453 total
includes taxes & fees
Aug 18 - Aug 19
Comfort Inn Chicago Southland I-80 & I-294 Near Casino
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

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

10/10 Excellent
"So amazing we booked a Christmas trip while we were there! The only thing we could say negatively was the pillows were very uncomfortable and when we called for additional or firmer pillows there were none available. But the rest of the experience was so good we’ll try to bring our own pillows next time."
Andrew 3-night trip
Posted 6 hours ago
Fairmont Chicago at Millennium Park