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Check prices for these dates

Next weekend
Aug 8 - Aug 10
In two weeks
Aug 15 - Aug 17
In one month
Aug 29 - Aug 31
In two months
Sep 26 - Sep 28

Browse Select Historic Route 66 Apartments

Clean & Equipped 1BR Apt
1 bedroom, iron/ironing board, WiFi, bed sheets

Clean & Equipped 1BR Apt

8.4 out of 10, Very good, (7)
The price is CA $131
CA $258 total
includes taxes & fees
Aug 5 - Aug 6
Clean & Equipped 1BR Apt
Lakeview 2BR Apartment
Fridge, microwave, oven, stovetop

Lakeview 2BR Apartment

9.4 out of 10, Exceptional, (6)
The price is CA $131
CA $286 total
includes taxes & fees
Aug 11 - Aug 12
Lakeview 2BR Apartment
White House at Grand Central
Comfort Apartment

White House at Grand Central

4.0 star property
8.6 out of 10, Excellent, (114)
"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 $148
CA $262 total
includes taxes & fees
Aug 3 - Aug 4
White House at Grand Central
Luxurious 3 Bedroom Apartment in Chicago
Microwave, oven, stovetop, dishwasher

Luxurious 3 Bedroom Apartment in Chicago

9.6 out of 10, Exceptional, (14)
"Great property! Would visit again!"
Luxurious 3 Bedroom Apartment in Chicago
Cozy studio in Andersonville Chicago
1 bedroom, iron/ironing board, free WiFi, bed sheets

Cozy studio in Andersonville Chicago

9.2 out of 10, Wonderful, (14)
"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 $124
CA $235 total
includes taxes & fees
Aug 11 - Aug 12
Cozy studio in Andersonville Chicago
Charming 2BR in Vibrant Lakeview
2 bedrooms, iron/ironing board, travel crib, WiFi

Charming 2BR in Vibrant Lakeview

9.8 out of 10, Exceptional, (6)
The price is CA $135
CA $290 total
includes taxes & fees
Aug 11 - Aug 12
Charming 2BR in Vibrant Lakeview
2-bedroom apartment just 2 minutes drive to Wrigley Field
Exterior

2-bedroom apartment just 2 minutes drive to Wrigley Field

2.0 star property
9.4 out of 10, Exceptional, (32)
"Easy to find, slept like a baby. "
The price is CA $222
CA $499 total
includes taxes & fees
Aug 12 - Aug 13
2-bedroom apartment just 2 minutes drive to Wrigley Field
Wrigley/Lakeview Gem- Walk to Wrigley Field/ Parking available!
Fridge, microwave, oven, stovetop

Wrigley/Lakeview Gem- Walk to Wrigley Field/ Parking available!

8.8 out of 10, Excellent, (33)
"It was what I thought it would be "
Wrigley/Lakeview Gem- Walk to Wrigley Field/ Parking available!
Michigan Ave 2BR: Balcony, Exclusive Access
Pool

Michigan Ave 2BR: Balcony, Exclusive Access

9.6 out of 10, Exceptional, (11)
"Roomy 2 bedroom with great hideaway beds.Excellent location easy to get everywhere. Super responsive hosts Nice building with gym and parking option for visitors "
Michigan Ave 2BR: Balcony, Exclusive Access
Spacious 3-bedroom apartment in gorgeous Chicago with WiFi, AC
Interior

Spacious 3-bedroom apartment in gorgeous Chicago with WiFi, AC

6.0 out of 10, (2)
"The property was great and exactly what we needed for our stay. We had 2 kids and 3 adults. The space was well laid out and the neighborhood was perfect. We could walk easily to grab coffee/snacks plus a grocery store with a park right around the corner. The property manager made check in and out very easy and was easily reached if there were questions!"
Spacious 3-bedroom apartment in gorgeous Chicago with WiFi, AC
Spacious 3-bedroom apartment near downtown, FREE PARKING
Private kitchen

Spacious 3-bedroom apartment near downtown, FREE PARKING

10.0 out of 10, Exceptional, (1)
"Extremely clean space that was perfect for our group. We didn't spend a lot of time in the home during our stay, but when we did it was fantastic. Only minor gripe would be the upstairs neighbors, they were occasionally quite loud and woke us up a few times in the middle of the night. Would absolutely stay here again, if/when we come back to the area."
The price is CA $137
CA $529 total
includes taxes & fees
Aug 4 - Aug 5
Spacious 3-bedroom apartment near downtown, FREE PARKING
Stylish City Reno Retreat!
Private kitchen

Stylish City Reno Retreat!

7.4 out of 10, Good, (6)
Stylish City Reno Retreat!
TOP RATED! FANTASTIC LOCATION! St. Louis near Delmar LOOP, WASHU, Forest Park!!!
2 bedrooms, iron/ironing board, WiFi, bed sheets

TOP RATED! FANTASTIC LOCATION! St. Louis near Delmar LOOP, WASHU, Forest Park!!!

9.6 out of 10, Exceptional, (8)
"Stayed with a girl group. Conveniently within walking distance of the loop and extremely comfortable for a group! Would highly recommend "
The price is CA $187
CA $456 total
includes taxes & fees
Aug 4 - Aug 5
TOP RATED! FANTASTIC LOCATION! St. Louis near Delmar LOOP, WASHU, Forest Park!!!
Charming Wrigleyville Home Close to the Cubs!
Exterior detail

Charming Wrigleyville Home Close to the Cubs!

9.4 out of 10, Exceptional, (25)
"Great neighborhood. Free and easy parking. "
Charming Wrigleyville Home Close to the Cubs!
Studio, sleeps 4, patio, short drive to Ski Resort, Six Flags & concert venues
Interior

Studio, sleeps 4, patio, short drive to Ski Resort, Six Flags & concert venues

2.0 star property
7.4 out of 10, Good, (20)
"The property was quiet and as expected. They were incredibly responsive and helpful with everything. "
The price is CA $93
CA $190 total
includes taxes & fees
Aug 3 - Aug 4
Studio, sleeps 4, patio, short drive to Ski Resort, Six Flags & concert venues
Cozy studio in charming Santa Fe
Property grounds

Cozy studio in charming Santa Fe

10.0 out of 10, Exceptional, (11)
"Spacious studio and comfy bed!!"
The price is CA $138
CA $269 total
includes taxes & fees
Aug 6 - Aug 7
Cozy studio in charming Santa Fe
Cozy 2-bedroom apartment in welcoming Chicago in the Wicker Park area
Smart TV

Cozy 2-bedroom apartment in welcoming Chicago in the Wicker Park area

9.0 out of 10, Wonderful, (7)
"We had a great time this weekend. Nice place to stay and close to our parking garage for Fan Fest. Might add some washcloths with the large bathroom towels. Would stay again. Thanks."
Cozy 2-bedroom apartment in welcoming Chicago in the Wicker Park area
Cozy Comfy Clean 420 Compliant FREE Parking QUIET Neighborhood A GUEST FAVORITE!
Pool

Cozy Comfy Clean 420 Compliant FREE Parking QUIET Neighborhood A GUEST FAVORITE!

10.0 out of 10, Exceptional, (104)
"We had an amazing stay at Jamie’s place. Quiet location, great host, and lovely accommodations. If you’re visiting Chicago, highly recommend staying at Jamie’s. "
Cozy Comfy Clean 420 Compliant FREE Parking QUIET Neighborhood A GUEST FAVORITE!
Elegant 3 Bedroom and 1 Bath Apartment
3 bedrooms, desk, iron/ironing board, free WiFi

Elegant 3 Bedroom and 1 Bath Apartment

9.2 out of 10, Wonderful, (12)
"Very nice place - can easily fit quite a few people! Host was very accommodating, place was clean and comfortable. My friends and I had a great time! "
Elegant 3 Bedroom and 1 Bath Apartment
3 Bedroom Loft overlooking water
Outdoor dining

3 Bedroom Loft overlooking water

9.6 out of 10, Exceptional, (110)
"We really enjoyed staying at this property; it was fantastic!"
3 Bedroom Loft overlooking water
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

Hyatt Regency Chicago

Hyatt Regency Chicago

10/10 Excellent
"A most enjoyable stay at this hotel"
Suzanne 2-night trip
Posted 17 hours ago
Hyatt Regency Chicago