Search Holiday Rentals in Historic Route 66

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
22 Jul - 23 Jul
Tomorrow
23 Jul - 24 Jul
This weekend
25 Jul - 27 Jul
Next weekend
1 Aug - 3 Aug

Top Holiday Rentals in Historic Route 66

Sentral Michigan Avenue
Relax in a spacious area with comfortable seating and lush greenery.

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (841)
"We would stay here again. Very happy with our stay "
The price is ₹16,065
₹21,391 total
includes taxes & fees
17 Aug - 18 Aug
Sentral Michigan Avenue
Junipine Resort
Relax in a serene outdoor space with a round table and six comfortable chairs, surrounded by trees and a wooden railing.

Junipine Resort

3.5 star property
9.2 out of 10, Wonderful, (2141)
"Very clean excellent location"
The price is ₹12,544
₹14,413 total
includes taxes & fees
18 Aug - 19 Aug
Junipine Resort
Sonder by Marriott Bonvoy Market Hall Apartments West Loop
Enjoy a minimalist retreat with a large bed, desk, and compact kitchenette.

Sonder by Marriott Bonvoy Market Hall Apartments West Loop

3.5 star property
8.4 out of 10, Very good, (328)
"Super cool spot in a great part of the city."
The price is ₹12,397
₹14,553 total
includes taxes & fees
17 Aug - 18 Aug
Sonder by Marriott Bonvoy Market Hall Apartments West Loop
Level Chicago – Old Town
Located in a bustling urban area, this high-rise building offers stunning city views.

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (331)
"Hotel was nice"
The price is ₹24,559
₹30,756 total
includes taxes & fees
19 Aug - 20 Aug
Level Chicago – Old Town
Kasa Magnificent Mile Chicago
Relax on the spacious balcony with a city view, featuring a sofa, armchair, and outdoor seating area.

Kasa Magnificent Mile Chicago

4.0 star property
9.4 out of 10, Exceptional, (447)
"Nice views and convenient location to transit and dining"
Kasa Magnificent Mile Chicago
Sonder by Marriott Bonvoy South Wabash Apartments South Loop
Enjoy a city view from the large window, with a comfortable sofa and potted plant adding to the inviting atmosphere.

Sonder by Marriott Bonvoy South Wabash Apartments South Loop

3.5 star property
8.8 out of 10, Excellent, (584)
"Great place and location. "
The price is ₹15,771
₹18,514 total
includes taxes & fees
21 Aug - 22 Aug
Sonder by Marriott Bonvoy South Wabash Apartments South Loop
Sonder by Marriott Bonvoy The Plymouth Apartments Loop
Enjoy the city view from this stylish balcony with a sofa, chair, and table.

Sonder by Marriott Bonvoy The Plymouth Apartments Loop

3.5 star property
8.0 out of 10, Very good, (121)
"Super convenient location. Lots of parking options and able to walk to all sites in this area."
The price is ₹12,030
₹14,122 total
includes taxes & fees
4 Aug - 5 Aug
Sonder by Marriott Bonvoy The Plymouth Apartments Loop
Kasa South Loop Chicago
Enjoy the city view from this balcony with a comfortable Adirondack chair and a small table.

Kasa South Loop Chicago

4.0 star property
9.4 out of 10, Exceptional, (320)
"I definitely enjoyed my stay and roof deck was the highlight. "
Kasa South Loop Chicago
Sonder by Marriott Bonvoy The Burnham Apartments Loop
Relax in style with plush armchairs and a natural centerpiece, surrounded by a contemporary design.

Sonder by Marriott Bonvoy The Burnham Apartments Loop

3.5 star property
9.0 out of 10, Wonderful, (196)
"Fantastically located snd brilliantly appointed aparthotel. Absolutely perfect for our stay, where we were competing at the HYROX world championships. The room was super spacious and had all amenities you could wish for. "
The price is ₹18,926
₹22,217 total
includes taxes & fees
17 Aug - 18 Aug
Sonder by Marriott Bonvoy The Burnham Apartments Loop
Fort Marcy Hotel Suites by All Seasons Resort Lodging
Stroll through lush gardens to a traditional building with a serene atmosphere.

Fort Marcy Hotel Suites by All Seasons Resort Lodging

3.0 star property
8.8 out of 10, Excellent, (2187)
"Great place, great stay! Strongly recommend giving this place a try. "
The price is ₹9,928
₹16,865 total
includes taxes & fees
11 Aug - 12 Aug
Fort Marcy Hotel Suites by All Seasons Resort Lodging
The Gem Museum Suites
Kitchen area with dining space, featuring a refrigerator, round table, and two chairs.

The Gem Museum Suites

3.5 star property
9.4 out of 10, Exceptional, (79)
"Excellent hotel. Would stay again."
The price is ₹19,503
₹22,328 total
includes taxes & fees
12 Aug - 13 Aug
The Gem Museum Suites
The Neighborhood Hotel-Little Italy
Welcome to The Neighborhood Hotel, where guests enter through a distinctive black brick facade with the hotel's name prominently displayed.

The Neighborhood Hotel-Little Italy

4.0 star property
9.8 out of 10, Exceptional, (177)
"Very nice and convenient option for a larger group that needs more beds. Walkable to an easy train to downtown. Plenty of food options on the block. Nice Kitchen and Laundry were very useful. "
The Neighborhood Hotel-Little Italy
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
Relax in this stylish living room with a sofa, armchair, and coffee table, offering a view of the city outside.

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 ₹13,864
₹16,275 total
includes taxes & fees
17 Aug - 18 Aug
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
Grand Canyon RV Glamping
Modern kitchen and living area with central island, stainless steel appliances, and a comfortable black leather sofa.

Grand Canyon RV Glamping

1.5 star property
9.0 out of 10, Wonderful, (561)
"Love staying at this property. "
The price is ₹7,340
₹15,268 total
includes taxes & fees
31 Jul - 1 Aug
Grand Canyon RV Glamping
Kasa River North Chicago
Meetings take place around a large, rectangular table surrounded by six chairs with chrome legs.

Kasa River North Chicago

4.0 star property
9.6 out of 10, Exceptional, (156)
"Great location and very clean! Will definitely be staying again. "
Kasa River North Chicago
Sonder by Marriott Bonvoy The Opal Apartments River North
Enjoy a panoramic city view from this rooftop terrace, featuring a round table, wicker chairs, and a sofa with a throw blanket.

Sonder by Marriott Bonvoy The Opal Apartments River North

3.5 star property
8.6 out of 10, Excellent, (42)
"Our stay was amazing. "
The price is ₹13,864
₹16,275 total
includes taxes & fees
21 Aug - 22 Aug
Sonder by Marriott Bonvoy The Opal Apartments River North
Arizona Mountain Inn and Cabins
Situated in a forested area, this cabin features a wooden deck and stone foundation, surrounded by tall pine trees.

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 ₹12,864
₹14,303 total
includes taxes & fees
4 Aug - 5 Aug
Arizona Mountain Inn and Cabins
MainStay Suites Springfield South - Battlefield Rd
Relax in a stylish room with a large bed, two bedside tables, and a comfortable sofa.

MainStay Suites Springfield South - Battlefield Rd

2.0 star property
8.6 out of 10, Excellent, (65)
"It is in a nice area with plenty of shopping, dining, coffee options. Our 2 bed, 2 bath room with a loft was perfect for a family of 4 with kids who are old enough to need privacy but too young for their own hotel room."
The price is ₹9,463
₹10,741 total
includes taxes & fees
28 Jul - 29 Jul
MainStay Suites Springfield South - Battlefield Rd
Comfort Inn Chicago Southland I-80 & I-294 Near Casino
Two single beds with white linens, a small armchair, and a bedside table with a lamp.

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

2.5 star property
3.6 out of 10, (48)
"the property is under renovation it should not be open. There were no amenities, i.e., ice. The room was clean. "
The price is ₹7,379
₹8,336 total
includes taxes & fees
23 Jul - 24 Jul
Comfort Inn Chicago Southland I-80 & I-294 Near Casino
All Towne Suites
Experience the elegant architecture of this multi-story hotel, featuring a symmetrical design and beautifully maintained surroundings.

All Towne Suites

2.0 star property
9.2 out of 10, Wonderful, (245)
"Great stay, lovely family owned property "
The price is ₹6,759
₹7,585 total
includes taxes & fees
24 Jul - 25 Jul
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Historic Route 66 Hotel Reviews

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

10/10 Excellent
"Great spacious suites for hubby & I. Clean hotel. Walking distance to mostly everywhere downtown. Kind & helpful staff. Would definitely stay here again."
Cheryl 4-night trip
Posted 20 hours ago
Hilton Chicago/Magnificent Mile Suites