Search Apartment Rentals in Historic Route 66

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Browse Select Historic Route 66 Apartments

White House at Grand Central
Comfort Apartment
White House at Grand Central
3.5 star property
8.6 out of 10, Excellent, (94)
"Nice place only thing I wish the housekeepers start mopping the floors "
The price is CA $93
CA $276 total
includes taxes & fees
Nov 19 - Nov 20
White House at Grand Central
1F Chicago's Little italy Graystone nearDowntown
Exterior
1F Chicago's Little italy Graystone nearDowntown
10.0 out of 10, Exceptional, (118)
"Great location walking distance of restaurants and some nightlife. Good neighborhood very safe college kids walking the streets not occasion. Are you really lazy lots of amenities more than usual in places like this and enjoyed our state would stay there again"
1F Chicago's Little italy Graystone nearDowntown
Historic Downtown Carriage House
Exterior
Historic Downtown Carriage House
10.0 out of 10, Exceptional, (157)
"The property is magical! The apartment is charming and had everything that we needed. The location is right downtown with easy access to all that historic Flagstaff has to offer. Highly recommend this stunning historic building to anyone looking for a beautiful space."
The price is CA $153
CA $296 total
includes taxes & fees
Dec 3 - Dec 4
Historic Downtown Carriage House
Cozy modern unit w/ easy access to downtown Chi
Exterior detail
Cozy modern unit w/ easy access to downtown Chi
9.6 out of 10, Exceptional, (33)
"Clean, exactly as described and reasonably priced. Also a great location to access public transit & lots of restaurants nearby. Had a great stay!"
Cozy modern unit w/ easy access to downtown Chi
Roscoe Village Inn | Guesthouse | Walk to Chicago's Wrigley Field
Exterior
Roscoe Village Inn | Guesthouse | Walk to Chicago's Wrigley Field
10.0 out of 10, Exceptional, (163)
"The location is close to the bus, and then easy to the Metro. It was about a 40ish min travel to the Art Institute when we were there. Roscoe Village is picturesque. There is a Starbucks at the end of the street if you want your pumpkin spice latte, but they've also got plenty of local talent- the owner of Rudy's Bakery (try the butter cookies YUM!!)-was lovely. There were plenty of other places--we just didn't have time! We arrived on Halloween; the entire neighborhood came out on their front...
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.
Terrace/patio
StL's ‘The Hill' NBHD. Famous for all things Italian. Cozy & clean 2nd fl apt.
10.0 out of 10, Exceptional, (242)
"We had a nice night in the comfortable property."
The price is CA $112
CA $215 total
includes taxes & fees
Nov 19 - Nov 20
StL's ‘The Hill' NBHD. Famous for all things Italian. Cozy & clean 2nd fl apt.
Chic & Historic Apartment Steps from Mag Mile
Fridge, microwave, oven, stovetop
Chic & Historic Apartment Steps from Mag Mile
9.8 out of 10, Exceptional, (25)
"This property was perfect for our weekend in Chicago. The surrounding area was cute and had lots of restaurant options. We were in town for the marathon so I appreciated being close by to a grocery store and the red line. The stop to the red line was a short walk and made getting to the start line a breeze."
Chic & Historic Apartment Steps from Mag Mile
Wrigley/Southport Corridor Garden Oasis +parking!
Exterior
Wrigley/Southport Corridor Garden Oasis +parking!
9.8 out of 10, Exceptional, (65)
"Property was very clean and well maintained. Great location! "
Wrigley/Southport Corridor Garden Oasis +parking!
The Lofts of North Main Street
Dining
The Lofts of North Main Street
9.6 out of 10, Exceptional, (112)
"Loved the vibe, location couldn’t have been better. The unit was clean and had everything we needed. "
The price is CA $181
CA $373 total
includes taxes & fees
Nov 20 - Nov 21
The Lofts of North Main Street
Cozy Soulard 2BR w/ Free Parking
Interior
Cozy Soulard 2BR w/ Free Parking
9.6 out of 10, Exceptional, (34)
"Thank you Joe for such a wonder stay!!!"
The price is CA $97
CA $239 total
includes taxes & fees
Nov 19 - Nov 20
Cozy Soulard 2BR w/ Free Parking
Chic, Cozy home, by Blue Line Train Stop + Free parking
Interior
Chic, Cozy home, by Blue Line Train Stop + Free parking
9.6 out of 10, Exceptional, (34)
"The house & the apartment were very clean & cute. Neighborhood was nice & felt safe. My only complaints were that we would’ve liked more than 2 bath towels for two people for 3 days. Also, it was very warm in the apartment (no air conditioning), but who could’ve known it would be 80 degrees in mid-October. Thank goodness there was one fan provided."
Chic, Cozy home, by Blue Line Train Stop + Free parking
Stylish FoxPark 3BR, King Master
Fridge, microwave, oven, stovetop
Stylish FoxPark 3BR, King Master
10.0 out of 10, Exceptional, (42)
"Week long stay, no complaints. Comfy beds, well stocked, clean, responsive host. Agree on rough stairs access but the city in general is not well maintained so watch for the potholes outside. "
The price is CA $98
CA $254 total
includes taxes & fees
Nov 19 - Nov 20
Stylish FoxPark 3BR, King Master
Stay in “STYLE” Apartment, close to CHI downtown
Fridge, microwave, oven, dishwasher
Stay in “STYLE” Apartment, close to CHI downtown
9.8 out of 10, Exceptional, (69)
"Clean space. Neighborhood felt safe. Beds are super hard though so not ideal for everyone. Also the blinds in the bedrooms don’t block out light very well so be prepared to be up when the sun is up if you stay here"
Stay in “STYLE” Apartment, close to CHI downtown
Spacious Bronzeville Gem Garden lvl Near Downtown, University of Chicago, Museum
Smart TV
Spacious Bronzeville Gem Garden lvl Near Downtown, University of Chicago, Museum
9.8 out of 10, Exceptional, (66)
"Rented with Valane for the marathon weekend. It was clean, quiet, away from the hustle of the city. It was super easy to navigate to expo, start lines, and sites. Loved jot beong couped up in a hotel room for the weekend Highly recommend Thank you so much for the great stay"
Spacious Bronzeville Gem Garden lvl Near Downtown, University of Chicago, Museum
Remodeled Kirkwood Guest house
Exterior
Remodeled Kirkwood Guest house
10.0 out of 10, Exceptional, (67)
"Nice family neighborhood, very quiet, rental is immaculate clean and looks new. We will be back. "
Remodeled Kirkwood Guest house
Historic Downtown Adobe Apartment near everything you want
Fridge, microwave, oven, stovetop
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 $148
CA $318 total
includes taxes & fees
Nov 17 - Nov 18
Historic Downtown Adobe Apartment near everything you want
The Holiday Lake House - 2br 2bth - 50 steps from the beach!
Property grounds
The Holiday Lake House - 2br 2bth - 50 steps from the beach!
10.0 out of 10, Exceptional, (34)
"Very clean and well thought out/supplied apartment on a lovely street a 30 second walk to Lake Michigan. There are 2 bedrooms, one larger master with en suite bathroom, and a second full bathroom and smaller bedroom. The unit is on the bottom floor so windows are high. Diane is friendly and responsive. The walk along the beach & out to an old lighthouse was a bonus. The street has mature trees and people walking dogs. There is a 7-11 on the corner and several restaurants walking distance. ...
The Holiday Lake House - 2br 2bth - 50 steps from the beach!
Bright Garden Studio
1 bedroom, desk, iron/ironing board, travel crib
Bright Garden Studio
8.6 out of 10, Excellent, (14)
"easy and close transit access, Owner is quick to respond once your stay has started, will need to be a heavy sleeper with above tenants late/early morning entrance. Other than that clean, comfy studio"
The price is CA $78
CA $288 total
includes taxes & fees
Nov 18 - Nov 19
Bright Garden Studio
Modern 2 King BR Apt, Relax in Style!!
Fridge, microwave, oven, stovetop
Modern 2 King BR Apt, Relax in Style!!
9.8 out of 10, Exceptional, (40)
"We loved staying outside of the city in this quiet neighborhood. We were conveniently located within an easy distance to get to everything we wanted throughout our stay. The house was spacious and clean. We loved how quiet the one way street is and would book this spot again."
Modern 2 King BR Apt, Relax in Style!!
3BR Spacious Home Away From Home
Fridge, microwave, oven, stovetop
3BR Spacious Home Away From Home
10.0 out of 10, Exceptional, (28)
"Stayed here while I was running the Chicago marathon. Was perfect for my infant and toddler and everything we needed for the weekend. Nice neighborhood, easy parking, great communication through the stay. Would definitely stay here again."
3BR Spacious Home Away From Home
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
Interior
Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (587)
"It was beautiful,clean and quiet "
The price is CA $162
CA $232 total
includes taxes & fees
Dec 10 - Dec 11
Sentral Michigan Avenue
Junipine Resort
Terrace/patio
Junipine Resort
3.5 star property
9.2 out of 10, Wonderful, (1924)
"Restaurant was not available for dinner because it was reserved for private party. "
The price is CA $328
CA $374 total
includes taxes & fees
Dec 2 - Dec 3
Junipine Resort
Sonder Market Hall
Interior
Sonder Market Hall
3.5 star property
8.6 out of 10, Excellent, (203)
"Overall, we really enjoyed our stay! The area was lovely and quiet, so nice to sit at the park right beside! I was worried about the noise when it came to sleeping, but I was able to sleep soundly (i did have noise cancelling headphones on though). The bed was super comyfy! The walls are thin though, we could hear conversations and music. This place was very accommodating! They have everything as stated in their listing. The kitchenette is so great! Staff was very friendly whenever I had...
The price is CA $96
CA $113 total
includes taxes & fees
Dec 10 - Dec 11
Sonder Market Hall
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.