Apartments in Historic Route 66

  • 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

Featured Apartments in Historic Route 66

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 NZ$283
includes taxes & fees
10 Feb - 11 Feb
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, (273)
"The apartment was clean, well-stocked and very comfortable. The location was perfect for close proximity to restaurants, shops, and coffee/tea shops. I would definitely stay here again."
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, (129)
"This is a very comfortable apartment with 2 bedrooms, a functional kitchen, lovely dining room, living room, and a nice small craft/puzzle room. We enjoyed having it as our home base during a visit to family in Lincoln Park. We will come back! "
Lakeview/LincolnPark 2BR/1BA Updated Vintage Apartment in walkable neighborhood

Historic Downtown Carriage House

10.0 out of 10, Exceptional, (164)
"Very Nice Accommodation! Comfortable and Convenient!"
The price is NZ$329
includes taxes & fees
10 Feb - 11 Feb
Historic Downtown Carriage House

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

10.0 out of 10, Exceptional, (211)
"My husband and I decided to book a last minute weekend getaway to The Hill and this property might have been the best part of the whole weekend!! Debbie and Joe were great host and extremely accommodating and helpful! The property is spacious but felt very cozy! The property is in the absolute best location on the Hill within walking distance to multiple iconic bars and restaurants! It’s a quiet area as well and easy to access at all times! The property was also extremely clean and had...
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 NZ$302
includes taxes & fees
10 Feb - 11 Feb
Cozy Soulard 2BR w/ Free Parking

The Lofts of North Main Street

9.6 out of 10, Exceptional, (123)
"Great location for a visit to old at charles"
The price is NZ$466
includes taxes & fees
10 Feb - 11 Feb
The Lofts of North Main Street

Wrigley/Southport Corridor Garden Oasis +parking!

9.8 out of 10, Exceptional, (72)
"Great property, perfect for two people. Easy walk to Wrigley. Stayed there on a couple cold winter days, and being a basement unit, the heater couldn’t keep up very well, so it was a little colder than ideal, but nothing a sweatshirt or extra blanket couldn’t fix. Would definitely go back!"
Wrigley/Southport Corridor Garden Oasis +parking!

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 NZ$486
includes taxes & fees
10 Feb - 11 Feb
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 NZ$280
includes taxes & fees
11 Feb - 12 Feb
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, (221)
"Great experience and the host was very accommodation!"
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, (30)
"Great communication with the owners. Very clean and lovely stay in a quiet neighborhood. "
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 NZ$319
includes taxes & fees
10 Feb - 11 Feb
Stylish FoxPark 3BR, King Master

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

9.6 out of 10, Exceptional, (27)
"Overall the studio was great. Only issue would be that the blinds are a little beat up but that’s not going to stop me from coming back!!"
The price is NZ$288
includes taxes & fees
12 Feb - 13 Feb
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 NZ$618
includes taxes & fees
10 Feb - 11 Feb
Luxury Cozy Loft Downtown STL
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, (675)
"Really loved the Apartment style suites"
The price is NZ$279
includes taxes & fees
10 Feb - 11 Feb
Sentral Michigan Avenue

Junipine Resort

3.5 star property
9.2 out of 10, Wonderful, (1963)
"Very nice property my kids loved it"
The price is NZ$328
includes taxes & fees
10 Feb - 11 Feb
Junipine Resort

Sonder Market Hall

3.5 star property
8.6 out of 10, Excellent, (252)
"It was wonderful!"
The price is NZ$234
includes taxes & fees
6 Mar - 7 Mar
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.