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Check prices for these dates

Next weekend
9 May - 11 May
In two weeks
16 May - 18 May
In one month
30 May - 1 Jun
In two months
27 Jun - 29 Jun

Featured Condo Rentals in Historic Route 66

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

Stunning 3 BR in prime Chicago location

9.8 out of 10, Exceptional, (94)
"We fully enjoyed our stay - location, space, communication were all excellent!"
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, (410)
"Great location, easy check-in and check-out, clean, comfortable and quiet. We thoroughly enjoyed staying here for our ski trip to Ski Santa Fe and will stay here again!"
Visitors Love the Location, I Love the View!
NEW LUXURY PENTHOUSE CONDO
Terrace/patio

NEW LUXURY PENTHOUSE CONDO

10.0 out of 10, Exceptional, (176)
"This property was great, would definitely return sometime. Has everything you need and then some. Property management was very easy to work with."
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, (32)
"Excellent stay. Great location."
Left Frame Lofts 210, Where history meets Luxury
Urban Chicago Vacation Rental Condo Near Beach!
Beach nearby

Urban Chicago Vacation Rental Condo Near Beach!

9.2 out of 10, Wonderful, (19)
"Great place to stay. Close to everything. Nice and clean "
Urban Chicago Vacation Rental Condo Near Beach!
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, (32)
"It was a great place to stay and very spacious!"
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, (67)
"We had a great stay at the rental. Stacy was an amazing host. We would definitely stay there again. "
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, (30)
"Easy check in and lovely stay- thank you!"
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, (225)
"Loved this place. It was quiet and clean and within minutes of everything we wanted to do. "
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, (144)
"This property was even better than advertised, per my adult children, who stayed there. It is not far from Santa Fe's central plaza and quite close to DeVargas Center, which is handy for grocery shopping."
Charming Santa Fe condo
Experience Chicago living near United Center
Fridge, microwave, oven, stovetop

Experience Chicago living near United Center

9.2 out of 10, Wonderful, (15)
"The place was amazing. The area is questionable but we didn't experience any problems while we stayed. "
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, (158)
"Very nice property—definitely would stay again"
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, (55)
"Clean and cozy"
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, (14)
"Great location near Southport corridor between two nearby stops on brown line. Good living space and clean. Host provided clear information about check-in and check-out with an information binder of nearby attractions. "
The price is NZ$752
includes taxes & fees
4 May - 5 May
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, (91)
"Great location and condo will definitely be back !"
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 enjoyed our stay in Rogers Park. The property was nice and a welcome retreat at the end of the day. "
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)
"Really nice condo, clean, comfy and accurate to vrbo ad. We would stay here again for sure. "
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
Unique to Santa Fe, this industrial condo is 5 mins to Railyard, 7 mins to Plaza
Fridge, microwave, oven, stovetop

Unique to Santa Fe, this industrial condo is 5 mins to Railyard, 7 mins to Plaza

10.0 out of 10, Exceptional, (11)
"Excellent accommodation with quick responses from the host"
Unique to Santa Fe, this industrial condo is 5 mins to Railyard, 7 mins to Plaza
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, (739)
"Great family place to stay. "
The price is NZ$333
includes taxes & fees
26 May - 27 May
Sentral Michigan Avenue
Sonder South Wabash
Superior Apartment, 1 Bedroom, Balcony, City View | Living area

Sonder South Wabash

3.5 star property
9.0 out of 10, Wonderful, (486)
"Great stay "
The price is NZ$216
includes taxes & fees
26 May - 27 May
Sonder South Wabash
Junipine Resort
Terrace/patio

Junipine Resort

3.5 star property
9.2 out of 10, Wonderful, (2060)
"Beautiful area Great restaurant "
The price is NZ$392
includes taxes & fees
27 May - 28 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.