Apartments in Historic Route 66 for Rent

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Compare 36 Apartments in Historic Route 66 with updated reviews, rates, and availability.

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 ¥12,536
¥33,181 total
includes taxes & fees
Jan 28 - Jan 29
White House at Grand Central

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

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

10.0 out of 10, Exceptional, (163)
"Comfortable and cute"
The price is ¥13,082
¥27,980 total
includes taxes & fees
Jan 23 - Jan 24
Historic Downtown Carriage House

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 ¥16,922
¥36,336 total
includes taxes & fees
Jan 23 - Jan 24
The Lofts of North Main Street

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 ¥10,712
¥26,499 total
includes taxes & fees
Jan 28 - Jan 29
Cozy Soulard 2BR w/ Free Parking

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

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

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

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

9.8 out of 10, Exceptional, (44)
"the property was clean "
The price is ¥10,557
¥27,869 total
includes taxes & fees
Feb 6 - Feb 7
Stylish FoxPark 3BR, King Master

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!

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

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

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

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

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

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 ¥21,609
¥39,040 total
includes taxes & fees
Feb 10 - Feb 11
Historic Oak Park Residence

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

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 ¥15,215
¥40,271 total
includes taxes & fees
Feb 12 - Feb 13
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.
Don't see what you're looking for?
See all available properties in Historic Route 66
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Historic Route 66

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 ¥17,023
¥24,540 total
includes taxes & fees
Jan 27 - Jan 28
Sentral Michigan Avenue

Sonder South Wabash

3.5 star property
9.0 out of 10, Wonderful, (419)
"Great place to spend a few days. "
The price is ¥17,106
¥20,081 total
includes taxes & fees
Jan 28 - Jan 29
Sonder South Wabash

Junipine Resort

3.5 star property
9.2 out of 10, Wonderful, (1956)
"Excellent just a few insects here and there it’s a cabin so whatever but the screen on the front door didn’t work which was a little strange. Over all excellent experience very relaxing."
The price is ¥29,124
¥33,172 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.