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Browse Select Historic Route 66 Apartments

Our top choices for Historic Route 66 apartments

Clean & Equipped 1BR Apt

8.4 out of 10, Very good, (15)
"Good experience. Would stay there again "
The price is CA $127
CA $280 total
includes taxes & fees
Sep 1 - Sep 2
Clean & Equipped 1BR Apt

Charming 2BR in Vibrant Lakeview

9.0 out of 10, Wonderful, (11)
The price is CA $130
CA $312 total
includes taxes & fees
Sep 3 - Sep 4
Charming 2BR in Vibrant Lakeview

Stylish 1BR in Lakeview Chicago

8.6 out of 10, Excellent, (12)
"This is a great apartment. It was very clean, well equipped kitchen and comfortable bed. Close to restaurants, grocery store, Starbucks and Wrigley Field. We could not find any parking on the street where the apartment is. I do recommend that you get in touch with the property owners couple of days prior to your visit because there is a vetting process prior to getting the keys to the apartment. "
The price is CA $144
CA $303 total
includes taxes & fees
Sep 2 - Sep 3
Stylish 1BR in Lakeview Chicago

Cozy, Fully Set-Up 1BR Space

9.0 out of 10, Wonderful, (17)
"Great place! 15 min walk to Wrigley "
The price is CA $127
CA $280 total
includes taxes & fees
Sep 2 - Sep 3
Cozy, Fully Set-Up 1BR Space

White House at Grand Central

4.0 star property
8.6 out of 10, Excellent, (116)
"It was very clean and nicely decorated. The house is a cool old building. The AC worked great (important, as it was super muggy outside.) I was only there for a couple nights but I think it would have worked well for a longer stay. "
The price is CA $119
CA $229 total
includes taxes & fees
Aug 27 - Aug 28
White House at Grand Central

Homey 1BR Space Apartment

9.0 out of 10, Wonderful, (4)
"Great location. Very walkable to restaurants and bars. Awesome park nearby. Host was easy to communicate with. "
The price is CA $118
CA $269 total
includes taxes & fees
Sep 16 - Sep 17
Homey 1BR Space Apartment

Cozy studio in Andersonville Chicago

9.2 out of 10, Wonderful, (22)
"It was a great location, internet was a little spotty on streaming services but we were in walking distance to so much it was worth it "
The price is CA $118
CA $230 total
includes taxes & fees
Sep 2 - Sep 3
Cozy studio in Andersonville Chicago

Nice 1BR Spot, Unwind & Relax

10.0 out of 10, Exceptional, (13)
"Super clean. Cozy. SAFE. Short drive to nearly every big attraction! Host was very communicative and kind!!"
The price is CA $118
CA $269 total
includes taxes & fees
Sep 2 - Sep 3
Nice 1BR Spot, Unwind & Relax

Luxurious 3 Bedroom Apartment in Chicago

9.2 out of 10, Wonderful, (22)
"Great property! Would visit again!"
Luxurious 3 Bedroom Apartment in Chicago

Lakeview 2BR Apartment

9.2 out of 10, Wonderful, (12)
"Great experience overall. Check-in was easy and the unit was very well kept. Very happy that we were so close to so much public transportation. It is a little noisy for those who aren’t used to hearing the L train nearby. Parking is hard to find, but there is paid parking nearby and easy to access public transit. If you plan on parking your car for the full time you’re there."
The price is CA $127
CA $309 total
includes taxes & fees
Sep 3 - Sep 4
Lakeview 2BR Apartment

Bright & Roomy 4BR in Pilsen

7.8 out of 10, Good, (7)
The price is CA $163
CA $408 total
includes taxes & fees
Sep 2 - Sep 3
Bright & Roomy 4BR in Pilsen

Your Perfect 2BR Home w/ Parking

8.0 out of 10, Very good, (4)
"Great location, close to United Center. Our host was super and was able to help me when I couldn't follow the instructions (lol). Wish I could have had a longer stay."
The price is CA $152
CA $350 total
includes taxes & fees
Sep 1 - Sep 2
Your Perfect 2BR Home w/ Parking

Secure carport, amazing Views and Reviews! Private suite with patio.

9.8 out of 10, Exceptional, (128)
"Location was easy and close to everything we wanted to see and do. Clean, comfortable and view was amazing. "
The price is CA $149
CA $239 total
includes taxes & fees
Aug 27 - Aug 28
Secure carport, amazing Views and Reviews! Private suite with patio.

Chic apartment with fitness room and AC in beautiful Chicago

7.0 out of 10, Good, (2)
"This was a nice apartment and stay forThe price. Close to train station. However would be nice to add a microwave. I had to reach out by calling the host after no response about check in information on VRBO app. Received the check in information very late the night prior to my stay. Was charged 50 for early check in but when we arrived they were stillCleaning and we had to wait about 15-20minutes outside. Overall with all the inconveniences. It ended up being good stay for the price. "
The price is CA $76
CA $338 total
includes taxes & fees
Aug 26 - Aug 27
Chic apartment with fitness room and AC in beautiful Chicago

Stylish City Reno Retreat!

7.4 out of 10, Good, (8)
"This property was not as we expected. The floor was disgustingly dirty, the dishwasher had food particles in it and smelled horrible (plus no dishwashing detergent to run a cycle), 1 roll of toilet paper, no replacement garbage bags, and opened food packages in the kitchen cabinets. I communicated these things to the owner and although he took forever to get back to me he did have someone drop off toilet paper, garbage bags, and dishwasher pods. The floor was so dirty that we needed to wear...
Stylish City Reno Retreat!

2-bedroom apartment just 2 minutes drive to Wrigley Field

2.0 star property
9.6 out of 10, Exceptional, (39)
"Great place to stay when you’re in town for the Cubbies! "
The price is CA $148
CA $403 total
includes taxes & fees
Aug 25 - Aug 26
2-bedroom apartment just 2 minutes drive to Wrigley Field

Walk Everywhere! 5 mins to Magnificent Mile, River

10.0 out of 10, Exceptional, (2)
"Excellent "
Walk Everywhere! 5 mins to Magnificent Mile, River

Huge Projector and Designated Workspace - Near Wrigley!

The price is CA $95
CA $408 total
includes taxes & fees
Sep 1 - Sep 2
Huge Projector and Designated Workspace - Near Wrigley!

Large Executive 1st Floor Apartment with Chefs Kitchen!

9.0 out of 10, Wonderful, (15)
"This place is beautiful! Comfortable bed, big kitchen. Nice living room area. Quiet and safe. We liked it a lot. "
Large Executive 1st Floor Apartment with Chefs Kitchen!

Lovely 1BR Apt in Lakeview

9.6 out of 10, Exceptional, (5)
The price is CA $127
CA $280 total
includes taxes & fees
Sep 2 - Sep 3
Lovely 1BR Apt in Lakeview
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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Top Historic Route 66 Hotel Reviews