Apartments in Historic Route 66 for Rent

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Compare 45 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)
"Very comfortable and laid back. It was nice to find a place where we felt safe right in the city. "
The price is ¥12,656
¥24,414 total
includes taxes & fees
Mar 2 - Mar 3
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, (275)
"In town for an event, the amenities and neighbourhood were very nice, the only down side was the noise considering that a we had early morning obligations"
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, (124)
"Clearly a lot of thought went into preparing the property and provided a beautiful place to come back to after being out all day. "
1F Chicago's Little italy Graystone nearDowntown

Lakeview/LincolnPark 2BR/1BA Updated Vintage Apartment in walkable neighborhood

9.8 out of 10, Exceptional, (130)
"We stayed two nights when in town to visit our daughter who attends college in Chicago. From start to finish we thoroughly enjoyed our stay! This is a beautiful property and a great location. The property managers were amazing throughout our stay. Simply gorgeous and can’t wait to come back."
Lakeview/LincolnPark 2BR/1BA Updated Vintage Apartment in walkable neighborhood

Historic Downtown Carriage House

10.0 out of 10, Exceptional, (165)
"Very Nice Accommodation! Comfortable and Convenient!"
The price is ¥13,285
¥27,648 total
includes taxes & fees
Feb 23 - Feb 24
Historic Downtown Carriage House

PREMIER LOCATION: HEART OF THE ITALIAN NBRHD, THE HILL, Dining&Shops Steps Away

10.0 out of 10, Exceptional, (213)
"The property was so very comfortable! This location was absolutely perfect with access to great restaurants and shops in The Hill. The street was surprisingly quiet given proximity to bars and houses. The church bells were not disturbing for us early risers. Only improvement would be blackout curtains on the bedroom windows to combat the street lights. "
PREMIER LOCATION: HEART OF THE ITALIAN NBRHD, THE HILL, Dining&Shops Steps Away

Cozy Soulard 2BR w/ Free Parking

9.6 out of 10, Exceptional, (41)
"We had a great 4 night stay at this property. From the time of booking through our stay, Joe was on top of making sure we had what we needed. He answered any questions we had right away and even came by to restock the coffee and get the tv signed back into the many streaming services he provides. Finding the place was super easy and we really appreciated the off street parking.There are lots of fun places to grab food and drinks within walking distance. When we ventured further, Ubers were...
The price is ¥10,300
¥25,479 total
includes taxes & fees
Feb 23 - Feb 24
Cozy Soulard 2BR w/ Free Parking

The Lofts of North Main Street

9.6 out of 10, Exceptional, (124)
"Spent 3 days in St Charles. This was our second visit to St. Charles, just a different season. An ice sculpture event was taking place on our first day. We loved the location. So close to everything we wanted to do. Able to walk everywhere. The condo was perfect for us. The 2 bathrooms, 2 bedrooms, gave us the privacy we needed. The open living room, kitchen area was very nice. The hosts were great to work with. Communication was quick and helpful. I would definitely rent this unit again. "
The price is ¥19,256
¥39,827 total
includes taxes & fees
Feb 24 - Feb 25
The Lofts of North Main Street

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

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

10.0 out of 10, Exceptional, (168)
"Hosts were responsive to our needs. Perfect location for our stay"
Roscoe Village Inn -Guesthouse - Walk to Chicago's Wrigley Field

Remodeled West Loop Apartment Near United Center

9.2 out of 10, Wonderful, (33)
"Beautiful apartment! We really enjoyed our time in Chicago. We ended up just parking across the street. It was easier, and there was always a spot available. There are many stairs leading up to the third floor apartment, so keep that in mind if you have mobility issues. The host texts you right back if you have concerns or questions."
Remodeled West Loop Apartment Near United Center

Apartment in the Heart of Downtown above an amazing Brewery!

9.8 out of 10, Exceptional, (21)
"The apartment is in a great location. The brewery downstairs has a decent menu and the designated parking spot is very close to the unit. I would stay here again. "
The price is ¥23,734
¥44,863 total
includes taxes & fees
Feb 24 - Feb 25
Apartment in the Heart of Downtown above an amazing Brewery!

The Sister Suite in Historic Downtown Flagstaff #4

9.8 out of 10, Exceptional, (71)
"I was visiting my son in college, and we had a great time together sharing this apartment for Veteran’s Day weekend. I loved not having keys and using door codes. It made check-in super easy the evening of our arrival. The apartment was cute, clean, and equipped with everything we needed. It was quiet and the thermostat was just right (keeping us warm). Great location too. Highly recommended!"
The price is ¥11,165
¥23,696 total
includes taxes & fees
Mar 3 - Mar 4
The Sister Suite in Historic Downtown Flagstaff #4

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

10.0 out of 10, Exceptional, (222)
"I’ve stayed at this host’s properties several times, and the places are all lovely and welcoming with lots of extra touches and conveniences!"
3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place

Entire Below Level Studio w/ Private Sauna

10.0 out of 10, Exceptional, (31)
"We loved the area and the place was easy to navigate as well as clean. LOVE the sauna. We will definitely be reaching back out when we visit in the spring."
Entire Below Level Studio w/ Private Sauna

Large, sunny 3 bedroom apartment two blocks from down town Oak Park.

10.0 out of 10, Exceptional, (102)
"Stayed with my husband and our two preteens. I grew up in Oak Park and chose this based off of location and it was perfect. Walkable neighborhood, close to the El and downtown Oak Park. The house was clean and comfortable, on top of having the quintessential Oak Park / Chicago vibe Communication was easy so was check in and out. I would choose to stay here again for sure!"
Large, sunny 3 bedroom apartment two blocks from down town Oak Park.

Stylish FoxPark 3BR, King Master

9.8 out of 10, Exceptional, (45)
"Would definitely consider this place again. Great host! Clean!"
The price is ¥10,150
¥26,795 total
includes taxes & fees
Feb 23 - Feb 24
Stylish FoxPark 3BR, King Master

The Music Studio, Historic FLG, Sleeps 3, Private & A/C!

9.6 out of 10, Exceptional, (28)
"Close to everything, cozy and the offsite laundry makes this one a great stay. Flagstaff is wonderful!"
The price is ¥10,467
¥24,379 total
includes taxes & fees
Feb 24 - Feb 25
The Music Studio, Historic FLG, Sleeps 3, Private & A/C!

Luxury Cozy Loft Downtown STL

9.6 out of 10, Exceptional, (14)
"We had a joyous and peaceful time! The place is spacious and looks just like the pictures. We had a minor issue with parking however, she was just one phone call away and she fixed it immediately. We called her on Christmas night with the issue and she was so kind and polite even though it was extremely late at night. Great communication skills!"
The price is ¥32,093
¥51,652 total
includes taxes & fees
Feb 23 - Feb 24
Luxury Cozy Loft Downtown STL

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
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, (681)
"This is a great hotel. The rooms have a kitchenette and the staff is wonderful! Beautiful hotel, great amenities. "
The price is ¥16,367
¥23,595 total
includes taxes & fees
Feb 24 - Feb 25
Sentral Michigan Avenue

Sonder South Wabash

3.5 star property
9.0 out of 10, Wonderful, (432)
"Loved the app and process for checking-in and out. The property itself could use some TLC, there were lots of scuff marks and scratches in the walls due to prior tenants. Our unit could have used a painting. There also wasn't a space to get extra toiletries per the app, would take this out if it's not really an option. "
The price is ¥14,323
¥16,814 total
includes taxes & fees
Mar 23 - Mar 24
Sonder South Wabash

Junipine Resort

3.5 star property
9.2 out of 10, Wonderful, (1973)
"It’s just a beautiful area "
The price is ¥27,963
¥32,129 total
includes taxes & fees
Feb 24 - Feb 25
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.