Search Apartment Rentals in Historic Route 66

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Check prices for these dates

Next weekend
Jan 31 - Feb 2
In two weeks
Feb 7 - Feb 9
In one month
Feb 21 - Feb 23
In two months
Mar 21 - Mar 23

Browse Select Historic Route 66 Apartments

White House at Grand Central
Comfort Apartment

White House at Grand Central

4.0 star property
8.6 out of 10, Excellent, (98)
"We realized that we have become adjusted to a king size bed. We missed having bedside tables as well. "
The price is CA $115
CA $306 total
includes taxes & fees
Jan 27 - Jan 28
White House at Grand Central
Bella Villa on Taylor Street Chicago’s Little Italy 1 mile west the Loop & UIC
Aerial view

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

10.0 out of 10, Exceptional, (271)
"Loved this hip 3 bedroom! Lots of art prints and tasteful decor. Well stocked kitchen and comfy beds. Neighborhood had many restaurant offerings."
Bella Villa on Taylor Street Chicago’s Little Italy 1 mile west the Loop & UIC
1F Chicago's Little italy Graystone nearDowntown
Exterior

1F Chicago's Little italy Graystone nearDowntown

10.0 out of 10, Exceptional, (123)
"Nice 3 bedroom, 2 bath in a quiet neighborhood The three of us loved this clean and cozy apartment. "
1F Chicago's Little italy Graystone nearDowntown
Historic Downtown Carriage House
Exterior

Historic Downtown Carriage House

10.0 out of 10, Exceptional, (163)
"Comfortable and cute"
The price is CA $120
CA $258 total
includes taxes & fees
Jan 23 - Jan 24
Historic Downtown Carriage House
The Lofts of North Main Street
Dining

The Lofts of North Main Street

9.6 out of 10, Exceptional, (121)
"Stayed for five nights while visiting family over the holidays. Plenty of space for 4 of us. Location was great…walking distance to shops, restaurants and bars. Place was clean. Checkout time was earlier than we are used to but owner did try to accommodate. Would stay again."
The price is CA $156
CA $335 total
includes taxes & fees
Jan 28 - Jan 29
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, (39)
"Great location close to the expressway , also had many places to eat and drink in walking distance. "
The price is CA $99
CA $244 total
includes taxes & fees
Jan 28 - Jan 29
Cozy Soulard 2BR w/ Free Parking
Wrigley/Southport Corridor Garden Oasis +parking!
Exterior

Wrigley/Southport Corridor Garden Oasis +parking!

9.8 out of 10, Exceptional, (70)
"convienent location "
Wrigley/Southport Corridor Garden Oasis +parking!
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, (167)
"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
Chic & Historic Apartment Steps from Mag Mile
Fridge, microwave, oven, stovetop

Chic & Historic Apartment Steps from Mag Mile

9.8 out of 10, Exceptional, (31)
"Great amenities, great location, spacious and comfortable. Check in a few days prior was difficult as the owner/manager didn’t message me or email me back… I had to call VRBO to have them investigate. Once they were made aware, smooth sailing from then on. Also, they listed a jacuzzi on site which was an error,and that was disappointing as I planned on that. Overall, despite these two things, great place ti stay! "
Chic & Historic Apartment Steps from Mag Mile
3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place
Point of interest

3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place

10.0 out of 10, Exceptional, (219)
"We had a group of couples coming to Chicago from different locations, and this was the perfect spot for us to be all together, but also have our own rooms and spaces. Everything was easy, and when we had a question on parking when we arrived later in the evening, John was very prompt in responding and helping us right away. "
3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place
Stylish FoxPark 3BR, King Master
Fridge, microwave, oven, stovetop

Stylish FoxPark 3BR, King Master

9.8 out of 10, Exceptional, (44)
"the property was clean "
The price is CA $97
CA $257 total
includes taxes & fees
Jan 23 - Jan 24
Stylish FoxPark 3BR, King Master
Spacious Bronzeville Gem Garden lvl Near Downtown, University of Chicago, Museum
Smart TV

Spacious Bronzeville Gem Garden lvl Near Downtown, University of Chicago, Museum

9.6 out of 10, Exceptional, (69)
"Nice place, not alot of parking "
Spacious Bronzeville Gem Garden lvl Near Downtown, University of Chicago, Museum
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, (39)
"This was a great place to celebrate the holidays. Kitchen was well stocked with cookware and utensils to make Christmas dinner and we had plenty of room to gather for game night. Beds were comfy and all amenities were in good condition. The apartment looks brand new! Loved the shampoo/conditioner/soap dispensers in the shower! Will definitely be back next Christmas. Thanks for the hospitality!"
The Holiday Lake House - 2br 2bth - 50 steps from the beach!
Chic, Cozy home, by Blue Line Train Stop + Free parking
Interior

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

9.4 out of 10, Exceptional, (42)
"Just as described and fit our needs perfectly. Super clean"
Chic, Cozy home, by Blue Line Train Stop + Free parking
2 New Construction Suites Same Place
TV

2 New Construction Suites Same Place

9.2 out of 10, Wonderful, (19)
"Great place to stay. Parking was great. Nice to have both places and the whole floor!"
2 New Construction Suites Same Place
Cozy modern unit w/ easy access to downtown Chi
Exterior detail

Cozy modern unit w/ easy access to downtown Chi

9.4 out of 10, Exceptional, (38)
"Wesley was super easy to work with. The area is great; the space is great; no complaints at all.Thanks again!"
Cozy modern unit w/ easy access to downtown Chi
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, (144)
"We loved how this location is under 15 minutes to Plaza. Great single story duplex. Clean and great host. "
Historic Downtown Adobe Apartment near everything you want
Historic Oak Park Residence
Exclusive Room, Private Bathroom, Garden View (2nd Floor) | Lounge

Historic Oak Park Residence

2.0 star property
9.6 out of 10, Exceptional, (7)
"A little difficult to find the driveway in the dark, but otherwise great. "
The price is CA $199
CA $360 total
includes taxes & fees
Feb 6 - Feb 7
Historic Oak Park Residence
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, (73)
"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
Bright Garden Studio
1 bedroom, desk, iron/ironing board, travel crib

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 $140
CA $371 total
includes taxes & fees
Feb 19 - Feb 20
Bright Garden Studio
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, (661)
"We stayed at Sentral after a trip to the Shedd with the kids. We had a great day and evening in the city and when we finally got to our room, we couldn't believe it! It was so spacious, we could have stayed for a week. Full kitchen, stocked with appliances, utensils, plates and glasses. Two full baths, two bedrooms and more closet space than we could have possibly used. Location was close to everything you'd need. We'll definitely be back."
The price is CA $157
CA $226 total
includes taxes & fees
Feb 3 - Feb 4
Sentral Michigan Avenue
Sonder South Wabash
Superior Apartment, 1 Bedroom, Balcony, City View | Living area

Sonder South Wabash

3.5 star property
9.0 out of 10, Wonderful, (418)
"I liked it a lot. The only detail that is important to me is the blackout on the windows, it let in a lot of light in the morning. For those who like to sleep in the dark, this is important. But there is nothing to criticize. We liked it a lot, we will definitely come back."
The price is CA $157
CA $185 total
includes taxes & fees
Jan 28 - Jan 29
Sonder South Wabash
Junipine Resort
Terrace/patio

Junipine Resort

3.5 star property
9.2 out of 10, Wonderful, (1956)
"Super clean, really nice place"
The price is CA $268
CA $305 total
includes taxes & fees
Jan 23 - Jan 24
Junipine Resort
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.