Search Condo Rentals in Historic Route 66

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Check prices for these dates

Next weekend
11 Apr - 13 Apr
In two weeks
18 Apr - 20 Apr
In one month
2 May - 4 May
In two months
30 May - 1 Jun

Compare 27 Condo Rentals in Historic Route 66 with updated reviews, rates, and availability.

Stunning 3 BR in prime Chicago location
Fridge, microwave, oven, stovetop

Stunning 3 BR in prime Chicago location

9.8 out of 10, Exceptional, (89)
"Accurate description of property. Host was very easy to communicate with. Would recommend!"
Stunning 3 BR in prime Chicago location
Visitors Love the Location, I Love the View!
Miscellaneous

Visitors Love the Location, I Love the View!

10.0 out of 10, Exceptional, (404)
"The condo was in a great location. Very comfortable for three people. "
Visitors Love the Location, I Love the View!
Modern Condo-Obama & University of Chicago Area
Fridge, microwave, oven, stovetop

Modern Condo-Obama & University of Chicago Area

9.4 out of 10, Exceptional, (6)
"Good area clean"
Modern Condo-Obama & University of Chicago Area
NEW LUXURY PENTHOUSE CONDO
Terrace/patio

NEW LUXURY PENTHOUSE CONDO

10.0 out of 10, Exceptional, (171)
"The property was clean, comfortable, and a great location. While the weather was not great during our visit, we tried to find as many pockets of time as possible to sit on the rooftop and take in the skyline. The parking spot in the garage was a huge added bonus. "
NEW LUXURY PENTHOUSE CONDO
Left Frame Lofts 210, Where history meets Luxury
Interior

Left Frame Lofts 210, Where history meets Luxury

9.6 out of 10, Exceptional, (27)
"A few small issues, but very quick response and was fixed. Very clean place and close to activities. Having a parking garage was nice. The view was amazing and the place very clean. Places to eat and get drinks within walking distance. "
The price is AED 584
AED 1,192 total
includes taxes & fees
13 Apr - 14 Apr
Left Frame Lofts 210, Where history meets Luxury
Pet-Friendly Urban Chicago Vacation Rental Condo
Beach nearby

Pet-Friendly Urban Chicago Vacation Rental Condo

9.0 out of 10, Wonderful, (16)
"This apartment was so cute, quiet and a great stay for my family and I. The host was able to accommodate extra blankets and towels for us during our stay. As well with it being a pet friendly property our dog enjoyed his stay and a little bit of the city life. Dinner is walkable as well as access to the main transit system. This is definitely a good spot for a girls trip or even a single that wanted to different kind of stay in Chicago!"
Pet-Friendly Urban Chicago Vacation Rental Condo
Experience Chicago living near United Center -
Fridge, microwave, oven, stovetop

Experience Chicago living near United Center -

9.2 out of 10, Wonderful, (24)
"overall place is good, the only bad thing is the location!"
Experience Chicago living near United Center -
Spacious 4BRCondo near Wrigley/Dtwn +FreeParking
Exterior

Spacious 4BRCondo near Wrigley/Dtwn +FreeParking

9.8 out of 10, Exceptional, (28)
"Specious and comfy. The balcony was not available, but we just needed the place for a few nights. Clean and nicely done"
Spacious 4BRCondo near Wrigley/Dtwn +FreeParking
Classic Lincoln Park 2 bedroom condo- parking included
Point of interest

Classic Lincoln Park 2 bedroom condo- parking included

9.8 out of 10, Exceptional, (64)
"I lived in Chicago for years and this was the first time I brought my son. It was exactly what I was hoping for. Walk up in an old building, restaurant on the bottom floor, transit a quick walk away."
Classic Lincoln Park 2 bedroom condo- parking included
3BR Modern Condo near Wrigley/Dwtn +Free Parking
Miscellaneous

3BR Modern Condo near Wrigley/Dwtn +Free Parking

9.4 out of 10, Exceptional, (28)
"I stayed here with my friends for my bachelorette weekend. We all had such a good time. It was a comfortable stay, the furniture was cute and clean. We had plenty of space. The beds and mattresses and pillows were so comfy. The listing was exactly as displayed online. Highly recommend!!!"
3BR Modern Condo near Wrigley/Dwtn +Free Parking
Perfect location for everything Santa Fe has to offer! Cool air conditioning
Exterior

Perfect location for everything Santa Fe has to offer! Cool air conditioning

9.8 out of 10, Exceptional, (222)
"Excellent property. Everything we needed and great location."
Perfect location for everything Santa Fe has to offer! Cool air conditioning
Charming Santa Fe condo
Fridge, microwave, oven, stovetop

Charming Santa Fe condo

10.0 out of 10, Exceptional, (142)
"The apartment was very comfortable. We lacked for nothing. Very tastefully decorated in southwest decor right down to the silverware. Extremely satisfied overall!"
Charming Santa Fe condo
Experience Chicago living near United Center
Fridge, microwave, oven, stovetop

Experience Chicago living near United Center

9.4 out of 10, Exceptional, (13)
"Everything was as advertised. Neighbors with dogs barking in the night and car honking/other outside elements can be disruptive if you're a light sleeper. Very quick and fast communication with host even at 2am. Would recommend."
Experience Chicago living near United Center
NEW LUXURY CONDO WITH PATIO DECK
Fridge, microwave, oven, stovetop

NEW LUXURY CONDO WITH PATIO DECK

10.0 out of 10, Exceptional, (157)
"This is the perfect place for you to stay when you’re in Chicago. We have stayed here at least four or five times already the place is immaculate. If you need any help someone is there for you ASAP. "
NEW LUXURY CONDO WITH PATIO DECK
Heart of Santa Fe - Charming 1 Bd/1 Bth Condo Casita with Private Courtyard!
Outdoor spa tub

Heart of Santa Fe - Charming 1 Bd/1 Bth Condo Casita with Private Courtyard!

9.8 out of 10, Exceptional, (54)
"Loved our stay there! The home was perfect and had everything we needed! Perfect communication with property manager. Street is very narrow but manageable! "
Heart of Santa Fe - Charming 1 Bd/1 Bth Condo Casita with Private Courtyard!
Chic Urban Retreat Near Wrigley Field w/Parking
Miscellaneous

Chic Urban Retreat Near Wrigley Field w/Parking

10.0 out of 10, Exceptional, (11)
"This was a great home base for our short family getaway to Chicago. Perfect amount of space for family of 4 to crash at the end of each day touristing around Chicago. Very clean. Great communication from hosts. Loved it."
Chic Urban Retreat Near Wrigley Field w/Parking
Wrigleyville Condo, Sleeps 10, 1/2 block from Wrigley Field
Smart TV, fireplace, printers

Wrigleyville Condo, Sleeps 10, 1/2 block from Wrigley Field

10.0 out of 10, Exceptional, (88)
"Property perfectly located near Wrigley Field, superbly clean and appointed."
Wrigleyville Condo, Sleeps 10, 1/2 block from Wrigley Field
Walking distance to restaurants, shops and Lake Michigan,
Exterior

Walking distance to restaurants, shops and Lake Michigan,

9.6 out of 10, Exceptional, (175)
"We were very pleased with the property. Stayed there over the Thanksgiving holiday & weekend while visiting my older daughter. Nice neighborhood & easy location to get to other parts of the city. Everything was as depicted in the description and communication with management was excellent. Would stay here again."
Walking distance to restaurants, shops and Lake Michigan,
Flagstaff Condo < 1 Mi to Golfing & Hiking!
Fridge, microwave, stovetop, dishwasher

Flagstaff Condo < 1 Mi to Golfing & Hiking!

9.8 out of 10, Exceptional, (47)
"Clean and quiet. Felt like home"
Flagstaff Condo < 1 Mi to Golfing & Hiking!
Spacious 3-bedroom, 2-bath condo, free parking/Oak Park
Fridge, microwave, oven, stovetop

Spacious 3-bedroom, 2-bath condo, free parking/Oak Park

9.0 out of 10, Wonderful, (26)
"Stayed here for my niece's bah mitzvah. There were 6 of us and it was the perfect size."
Spacious 3-bedroom, 2-bath condo, free parking/Oak Park
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
Interior

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (722)
"I like the view of this place, had a good few of the park and could see Michigan lake in the distance. Pretty cool that it had a wash and dryer, was not expecting that when we came. Like that it’s in walking distance from the museums, made traveling easy. Employees were also very helpful. "
The price is AED 403
AED 581 total
includes taxes & fees
7 Apr - 8 Apr
Sentral Michigan Avenue
Sonder South Wabash
Superior Apartment, 1 Bedroom, Balcony, City View | Living area | 36-inch flat-screen TV with digital channels, TV

Sonder South Wabash

3.5 star property
9.0 out of 10, Wonderful, (463)
"Great!"
The price is AED 403
AED 473 total
includes taxes & fees
16 Apr - 17 Apr
Sonder South Wabash
Junipine Resort
Terrace/patio

Junipine Resort

3.5 star property
9.2 out of 10, Wonderful, (2031)
"Many times we've stayed at Junipine, and without exception, we have a great time and the property is certainly part of our enjoyment. Having decks on every unit is part of the allure for us. The resort is mature but well maintained. We'll be back."
The price is AED 1,058
AED 1,215 total
includes taxes & fees
5 May - 6 May
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.