Apartments in Historic Route 66

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Featured Apartments in Historic Route 66

White House at Grand Central

4.0 star property
8.8 out of 10, Excellent, (97)
"We realized that we have become adjusted to a king size bed. We missed having bedside tables as well. "
The price is AU$314
includes taxes & fees
30 Dec - 31 Dec
White House at Grand Central

Wrigley/Southport Corridor Garden Oasis +parking!

9.8 out of 10, Exceptional, (68)
"Very clean and comfortable place!"
Wrigley/Southport Corridor Garden Oasis +parking!

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

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

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

9.4 out of 10, Exceptional, (38)
"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

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

10.0 out of 10, Exceptional, (267)
"Clean, comfortable and communication was great. Would recommend. "
Bella Villa on Taylor Street Chicago’s Little Italy 1 mile west the Loop & UIC

Historic Downtown Adobe Apartment near everything you want

9.8 out of 10, Exceptional, (140)
"A thoughtfully furnished home for guests. We enjoyed our stay."
The price is AU$371
includes taxes & fees
6 Jan - 7 Jan 2025
Historic Downtown Adobe Apartment near everything you want

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

Cozy Soulard 2BR w/ Free Parking

9.6 out of 10, Exceptional, (37)
"Great location close to the expressway , also had many places to eat and drink in walking distance. "
The price is AU$277
includes taxes & fees
7 Jan - 8 Jan 2025
Cozy Soulard 2BR w/ 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

Historic Downtown Carriage House

10.0 out of 10, Exceptional, (159)
"I recently had the pleasure of staying at a historic carriage house in downtown Flagstaff, Arizona, and it was an absolutely delightful experience. The location was perfect, within walking distance to all the attractions downtown, and just a short stroll to a local playhouse where we enjoyed a fantastic performance of Elf the Musical. The property itself was impeccably clean and beautifully furnished with super cute antiques that added a unique charm to the space. The hosts were incredibly nice...
The price is AU$329
includes taxes & fees
6 Jan - 7 Jan 2025
Historic Downtown Carriage House

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

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

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

10.0 out of 10, Exceptional, (246)
"We stayed in the lower unit a couple years ago and stayed in the upper unit this time. Great place and hosts, just as we expected. Super easy to get in and check out. Perfect location for us too! Thank you. "
The price is AU$249
includes taxes & fees
14 Jan - 15 Jan 2025
StL's ‘The Hill' NBHD. Famous for all things Italian. Cozy & clean 2nd fl apt.

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 AU$216
includes taxes & fees
2 Jan - 3 Jan 2025
Hummingbird House (Unit B)

The Lofts of North Main Street

9.6 out of 10, Exceptional, (116)
"Loved the vibe, location couldn’t have been better. The unit was clean and had everything we needed. "
The price is AU$429
includes taxes & fees
30 Dec - 31 Dec
The Lofts of North Main Street

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

Historic Oak Park Residence

2.0 star property
9.4 out of 10, Exceptional, (6)
"This was quite a charming home. The access to public transportation was great. One mile walk or drive to parking garage. We ventured into the city every day but could have easily stayed in Oak Park."
The price is AU$394
includes taxes & fees
9 Jan - 10 Jan 2025
Historic Oak Park Residence

Cozy modern unit w/ easy access to downtown Chi

9.4 out of 10, Exceptional, (37)
"Me and my sons were in town for a football game and enjoyed our stay in this comfortable basement apartment. Oak Park is a great little suburb of Chicago with a great selections of restaurants and nearby shopping. The hosts were easy to communicate with when our code to get in the apartment didn’t work. World recommend this place for smaller parties 3-4 people and would stay here again."
Cozy modern unit w/ easy access to downtown Chi
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, (629)
"I have stayed at this property 3 times now and every time has been amazing. They have become the only place I will stay at in the city. The location is great with a parking garage around the corner at is very cheap. You get so many more amenities than a hotel and is an overall great experience. I highly recommend."
The price is AU$253
includes taxes & fees
8 Jan - 9 Jan 2025
Sentral Michigan Avenue

Junipine Resort

3.5 star property
9.2 out of 10, Wonderful, (1940)
"Amazing stay at a beautiful property. Far exceeded our expectations. Beautiful views"
The price is AU$388
includes taxes & fees
5 Jan - 6 Jan 2025
Junipine Resort

Kasa Magnificent Mile Chicago

4.0 star property
9.2 out of 10, Wonderful, (343)
"The property location was great. The room was very spacious. The only knock was there was not a tv in the bedroom."
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.