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Our top choices for Historic Route 66 apartments

Ground-Floor Forest Park Studio | Parking, Washer/Dryer & Fast Wi-Fi

Ground-Floor Forest Park Studio | Parking, Washer/Dryer & Fast Wi-Fi
Maplewood
9.0 out of 10, Wonderful, (2)
"There were parks and streets that I walked my dog but there was no enclosed pet area as listed.Otherwise the place was exactly as listed and convenient location. Nice neighborhood, nice place."
United States
ann r.
The price is AED 279
AED 598 total
includes taxes & fees
22 Dec - 23 Dec
Ground-Floor Forest Park Studio | Parking, Washer/Dryer & Fast Wi-Fi

ENVITAE Hotel 4 Bedroom Luxury Apartments

ENVITAE Hotel 4 Bedroom Luxury Apartments
2.0 star property
Near North Side
10.0 out of 10, Exceptional, (8)
"We loved at our stay at this property. It was one of the best stays we have had on vacation."
United States
Javeria
The price is AED 3,237
AED 4,572 total
includes taxes & fees
18 Dec - 19 Dec
ENVITAE Hotel 4 Bedroom Luxury Apartments

Gold Coast Living: Modern Studio Unit

Gold Coast Living: Modern Studio Unit
Downtown Chicago
10.0 out of 10, Exceptional, (4)
"The communication was really effective and made for a smooth check in and check out process. Host was friendly and made great recommendations, 10/10 would stay again!"
United States
Seynabou
The price is AED 253
AED 608 total
includes taxes & fees
1 Jan - 2 January 2026
Gold Coast Living: Modern Studio Unit

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)
"The neighborhood was so clean and quiet. Friendly neighbors. Perfect location, not far from everything downtown. "
United States
Shederia P.
The price is AED 290
AED 756 total
includes taxes & fees
16 Dec - 17 Dec
Twice as Nice: Chic 2BR Stay with Style & Space

West Loop Living – Bright 1BR

West Loop Living – Bright 1BR
Downtown Chicago
10.0 out of 10, Exceptional, (4)
"Well-outfitted, nice apartment. Nearby (walkable) Jewel-Osco grocery, restaurants, and pay-parking. Moderate noise from nearby Chicago "L" Green Line."
United States
Jeffrey
The price is AED 231
AED 619 total
includes taxes & fees
4 Jan - 5 January 2026
West Loop Living – Bright 1BR

Modern West Loop Gem-City Views & Prime Location 4

Modern West Loop Gem-City Views & Prime Location 4
2.0 star property
Downtown Chicago
10.0 out of 10, Exceptional, (2)
"Amazing accommodation"
United States
Jiri N.
The price is AED 499
AED 1,353 total
includes taxes & fees
22 Dec - 23 Dec
Modern West Loop Gem-City Views & Prime Location 4

Sun-Drenched 1BR Apartment

Sun-Drenched 1BR Apartment
Downtown Chicago
10.0 out of 10, Exceptional, (2)
"Host was very friendly and informative. Place was clean and close to lots of fun. Trains loud and busy but knew that going in. "
United States
Tyler B.
The price is AED 231
AED 619 total
includes taxes & fees
6 Jan - 7 January 2026
Sun-Drenched 1BR Apartment

The One: A 1BR Stay That Feels Like Home

The One: A 1BR Stay That Feels Like Home
Downtown Chicago
8.4 out of 10, Very Good, (5)
"Very nice condo in a quiet neighborhood"
Canada
Patrick
The price is AED 231
AED 619 total
includes taxes & fees
1 Jan - 2 January 2026
The One: A 1BR Stay That Feels Like Home

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 AED 231
AED 619 total
includes taxes & fees
1 Jan - 2 January 2026
Stylish 1BR in West Loop

Your Chicago get Away

Your Chicago get Away
Downtown Chicago
8.4 out of 10, Very Good, (8)
"Clean, simple space close to the parks at the waterfront (Millennium, Grant, etc) and several spots for coffee. A bit of an odd building location (it's in a dorm tower with a laundry space next door! Not noisy tho) but easy to access at all hours, nice view as pictured."
United States
Pip M.
The price is AED 648
AED 1,403 total
includes taxes & fees
15 Dec - 16 Dec
Your Chicago get Away

Sleek 1BR Apt w/ Laundry

Sleek 1BR Apt w/ Laundry
Downtown Chicago
10.0 out of 10, Exceptional, (1)
"I was a little hesitant since I didn’t see any reviews, and was bit nervous. However, all that was put to rest when we arrived. Everything was as described and the photos were accurate. It was clean and minimalistic. Nice space for two for a week. Having the full kitchen was great. About 15 min walk to the brown line and 25 to the blue Line and not a lot of restaurants close by is about the only complaint. Bed could have been more comfortable too."
United States
Anonymous traveler
The price is AED 231
AED 619 total
includes taxes & fees
4 Jan - 5 January 2026
Sleek 1BR Apt w/ Laundry

Spacious 4BR Central Apartment w/ Skyline Views

Spacious 4BR Central Apartment w/ Skyline Views
Near North Side
10.0 out of 10, Exceptional, (8)
"Great stay. Very clean. Comfortable beds. Great location "
United States
shannon u.
The price is AED 2,310
AED 4,129 total
includes taxes & fees
18 Dec - 19 Dec
Spacious 4BR Central Apartment w/ Skyline Views

Modern West Loop Gem-City Views & Prime Location 3

Modern West Loop Gem-City Views & Prime Location 3
2.0 star property
Downtown Chicago
10.0 out of 10, Exceptional, (1)
"The host communicated everything very well. The short videos sent giving info about all the things you'd need to know were super helpful!"
United States
Laurie A.
The price is AED 562
AED 1,435 total
includes taxes & fees
30 Dec - 31 Dec
Modern West Loop Gem-City Views & Prime Location 3

Modern West Loop Gem-City Views & Prime Location 5

Modern West Loop Gem-City Views & Prime Location 5
2.0 star property
Downtown Chicago
8.0 out of 10, Very Good, (1)
"Great location, plenty of space and clean home. "
United States
Brittany T.
The price is AED 492
AED 1,344 total
includes taxes & fees
29 Dec - 30 Dec
Modern West Loop Gem-City Views & Prime Location 5

River North Private Deck With In and Out Parking

River North Private Deck With In and Out Parking
Downtown Chicago
10.0 out of 10, Exceptional, (3)
"The property was exactly as advertised; clean, good neighborhood, and the views of the city were great. The private outdoor patio access was fantastic."
United States
Rich G.
The price is AED 1,366
AED 2,540 total
includes taxes & fees
26 Dec - 27 Dec
River North Private Deck With In and Out Parking

Crossroads Studio: Steps Away from Historic Rt. 66 and Carthage Square

Crossroads Studio: Steps Away from Historic Rt. 66 and Carthage Square
Carthage
10.0 out of 10, Exceptional, (72)
"Great hosts "
United States
Leanna Z.
The price is AED 345
AED 545 total
includes taxes & fees
19 Dec - 20 Dec
Crossroads Studio: Steps Away from Historic Rt. 66 and Carthage Square

Cozy Studio in Heart of OKC Plaza District!

Cozy Studio in Heart of OKC Plaza District!
3.0 star property
Central Oklahoma City
10.0 out of 10, Exceptional, (1)
"We even left something behind, and they were happy to coordinate the forwarding. Very above and beyond."
United States
Kevin
The price is AED 165
AED 436 total
includes taxes & fees
15 Dec - 16 Dec
Cozy Studio in Heart of OKC Plaza District!

Stylish South City King 1BR Apt

Stylish South City King 1BR Apt
2.0 star property
Marine Villa
10.0 out of 10, Exceptional, (9)
"Great location, great accommodations, great host."
United States
Scott W.
The price is AED 294
AED 656 total
includes taxes & fees
21 Dec - 22 Dec
Stylish South City King 1BR Apt

Charming Farmhouse Loft with access to hot tub.

Charming Farmhouse Loft with access to hot tub.
3.5 star property
Claremore
10.0 out of 10, Exceptional, (17)
"Wonderful stay"
United States
Kathryn
The price is AED 261
AED 361 total
includes taxes & fees
18 Dec - 19 Dec
Charming Farmhouse Loft with access to hot tub.

The Courtyard Suite, Pool is open May to August

The Courtyard Suite, Pool is open May to August
Joplin
9.0 out of 10, Wonderful, (25)
"The Courtyard was so peaceful and cozy that I didn't want to come home!"
United States
Amy
The price is AED 220
AED 486 total
includes taxes & fees
18 Dec - 19 Dec
The Courtyard Suite, Pool is open May to August
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