Search Apartment Rentals in Historic Route 66

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Browse Select Historic Route 66 Apartments

White House at Grand Central

4.0 star property
8.8 out of 10, Excellent, (96)
"We realized that we have become adjusted to a king size bed. We missed having bedside tables as well. "
The price is CA $99
CA $287 total
includes taxes & fees
Jan 19 - Jan 20, 2025
White House at Grand Central

1F Chicago's Little italy Graystone nearDowntown

10.0 out of 10, Exceptional, (119)
"John had the apartment well stocked with coffee, teas, candy, towels, toiletries, and warm robes. Bed were comfy with nice bedding. We would stay here again!! "
1F Chicago's Little italy Graystone nearDowntown

Wrigley/Southport Corridor Garden Oasis +parking!

9.8 out of 10, Exceptional, (67)
"Very clean and comfortable place!"
Wrigley/Southport Corridor Garden Oasis +parking!

Vintage Graystone in Little Italy near the loop UIC United Ct & McCormick Place

10.0 out of 10, Exceptional, (216)
"What a beautiful apartment...and the Christmas decorations were so lovely."
Vintage Graystone in Little Italy near the loop UIC United Ct & McCormick Place

Bella Villa on Taylor Street Chicago’s Little Italy 1 mile west the Loop & UIC

10.0 out of 10, Exceptional, (266)
"Clean, comfortable and communication was great. Would recommend. "
Bella Villa on Taylor Street Chicago’s Little Italy 1 mile west the Loop & UIC

Roscoe Village Inn | Guesthouse | Walk to Chicago's Wrigley Field

10.0 out of 10, Exceptional, (166)
"Fantastic location and an outstanding host! I had an amazing stay. The space was ideal for my needs, offering a comfortable and convenient setting to assist my daughter with her wedding preparations. It had everything I was looking for—well-equipped with great amenities and in a prime location. The property was spotless, peaceful, and provided everything needed for a smooth and enjoyable experience. Easy street parking was always available! I highly recommend this place to anyone looking for a...
Roscoe Village Inn | Guesthouse | Walk to Chicago's Wrigley Field

Historic Downtown Adobe Apartment near everything you want

9.8 out of 10, Exceptional, (139)
"A thoughtfully furnished home for guests. We enjoyed our stay."
The price is CA $152
CA $329 total
includes taxes & fees
Dec 25 - Dec 26
Historic Downtown Adobe Apartment near everything you want

Stay in “STYLE” Apartment, close to CHI downtown

9.8 out of 10, Exceptional, (72)
"This is the 3rd time I’ve booked this Ukrainian Village apartment. It’s comfortable and has everything needed for visits into the city. "
Stay in “STYLE” Apartment, close to CHI downtown

Cozy Soulard 2BR w/ Free Parking

9.6 out of 10, Exceptional, (37)
"Great location!!! "
The price is CA $99
CA $244 total
includes taxes & fees
Jan 14 - Jan 15, 2025
Cozy Soulard 2BR w/ Free Parking

Chic, Cozy home, by Blue Line Train Stop + Free parking

9.6 out of 10, Exceptional, (37)
"I'd stay again, it was nice. Only issue was the upstairs neighbor must have been doing remodeling because the entire day was filled with hammers, drills, stomping etc. But all in all I enjoyed it."
Chic, Cozy home, by Blue Line Train Stop + Free parking

PET FRIENDLY! Unique Converted Storefront Stay - Great Neighborhood! by AllSet Turnover

9.4 out of 10, Exceptional, (26)
"Nice open space with large bedrooms. Quiet and clean! Perfect location to walk to local restaurants and shops "
PET FRIENDLY! Unique Converted Storefront Stay - Great Neighborhood! by AllSet Turnover

StL's ‘The Hill' NBHD. Famous for all things Italian. Cozy & clean 2nd fl apt.

10.0 out of 10, Exceptional, (245)
"Very nice stay in The HIll. This property is located very close to Cunetto's which is one of my favorite spots. The apartment is super nice and exactly as represented. Parking is easy which is saying something in the Hill. "
The price is CA $115
CA $220 total
includes taxes & fees
Jan 5 - Jan 6, 2025
StL's ‘The Hill' NBHD. Famous for all things Italian. Cozy & clean 2nd fl apt.

The Lofts of North Main Street

9.6 out of 10, Exceptional, (115)
"Loved the vibe, location couldn’t have been better. The unit was clean and had everything we needed. "
The price is CA $187
CA $383 total
includes taxes & fees
Dec 30 - Dec 31
The Lofts of North Main Street

Chic & Historic Apartment Steps from Mag Mile

9.8 out of 10, Exceptional, (29)
"We very much enjoyed our stay at this property! We were visiting Chicago for a fun weekend trip to celebrate our anniversary. The location was on a quiet street but within close walking distance to plenty of restaurants and shopping. The apartment was clean and very quiet in a beautiful, historic building. We highly recommend Tempo Cafe for breakfast. On our last morning in town, we actually saw Larry David, Jeff Garlin and Susie Essman at brunch there! "
Chic & Historic Apartment Steps from Mag Mile

Stylish FoxPark 3BR, King Master

10.0 out of 10, Exceptional, (43)
"the property was clean "
The price is CA $101
CA $263 total
includes taxes & fees
Jan 6 - Jan 7, 2025
Stylish FoxPark 3BR, King Master

Bright Garden Studio

8.8 out of 10, Excellent, (16)
"We had a great stay in this Evanston lower level studio apartment while in town for our reunion and Homecoming weekend at Northwestern. The studio is clean, nicely decorated, good amenities, and conveniently located to both the NU campus and downtown Chicago. Having a dedicated parking spot was awesome too, as the off-street parking fills up quickly in the evening. My only recommendation would be replacing the really firm mattress with a softer one, or a memory foam topper. All in all we had...
The price is CA $192
CA $433 total
includes taxes & fees
Jan 5 - Jan 6, 2025
Bright Garden Studio

Historic Second floor 2 Bedroom Apartment

9.4 out of 10, Exceptional, (30)
"The property is exactly how it is described in the listing. We rented the property for a weekend with our boys before school started. The property is an easy quick drive to all the attractions. We visited the Arch and went to a Card’s game and it was only an 8 minute drive to each. Great communication with host and very thankful for a late check out. We would definitely rent again. "
Historic Second floor 2 Bedroom Apartment

Hummingbird House (Unit B)

9.2 out of 10, Wonderful, (15)
"Fab place with everything we needed in sweet neighbourhood. Would stay again."
The price is CA $68
CA $192 total
includes taxes & fees
Jan 2 - Jan 3, 2025
Hummingbird House (Unit B)

3BR Spacious Home Away From Home

10.0 out of 10, Exceptional, (29)
"Everything was very nicely laid out and organized. Everything was pretty clean. We did not realize that it was just the one floor though and that there would be people above us. That could be better advertised in the description of the property. Other than that it was very good. "
3BR Spacious Home Away From Home

Remodeled Kirkwood Guest house

10.0 out of 10, Exceptional, (69)
"Really nice place. Private, clean, and comfortable. "
Remodeled Kirkwood Guest house
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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Other property types in Historic Route 66

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (623)
"We stayed at the Sentral with friends to take in the holiday sights around Chicago. The room was spacious and clean, though a little worn in areas. Having a kitchen, plus a washer & dryer was great. And the city views were incredible. The amenities (pool, gym, game room) on the 7th floor were phenomenal! We found cheaper parking in a nearby garage, but the valet option is nice. And having restaurants and a grocery nearby was super convenient."
The price is CA $166
CA $237 total
includes taxes & fees
Jan 12 - Jan 13, 2025
Sentral Michigan Avenue

Junipine Resort

3.5 star property
9.2 out of 10, Wonderful, (1937)
"Absolutely beautiful property"
The price is CA $399
CA $455 total
includes taxes & fees
Dec 22 - Dec 23
Junipine Resort

Kasa Magnificent Mile Chicago

4.0 star property
9.2 out of 10, Wonderful, (342)
"Good location. Full kitchen and clothes washer/dryer in suite were awesome amenities! Blinds were missing a few blades which was annoying. Tub could use a reglaze parking is close by but having a deal with the lot would be nice"
Kasa Magnificent Mile Chicago
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.