Highland Park Vacation Rentals

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Vacation Rentals in Highland Park

Great 3 bedroom rental unit near Logan Square

Chicago IL

With a stay at this vacation home, you'll be centrally located in Chicago, within a 15-minute drive of Wrigley Field and United Center.

Kitchen

Washer

Spacious 3BR Duplex for Groups-Near Airport & Downtown-Cozy & Quiet

Chicago IL

With a stay at this vacation home in Chicago (Jefferson Park), you'll be within a 15-minute drive of Wrigley Field and Chicago Riverwalk.

Kitchen

Washer

Wrigley Field/Lakeview -Entire Home- Large Groups!

Chicago IL

With a stay at this vacation home, you'll be centrally located in Chicago, within a 5-minute drive of Wrigley Field and Lake Michigan.

Kitchen

Washer

Insta Worthy ^Prime Spot ^Patio ^Parking ^Fireplace

Chicago IL

With a stay at this vacation home, you'll be centrally located in Chicago, within a 5-minute drive of Michigan Avenue and Lake Michigan.

Kitchen

Washer

Lake/Beach Getaway (Remodeled)

Round Lake Beach IL

When you stay at this vacation home in Round Lake Beach, you'll be within a 10-minute drive of College of Lake County and Jones Island Beach.

Washer

Dryer

Belmont House, Classy & Chic/walk to Wrigley Field

Chicago IL

With a stay at this vacation home in Chicago (Lakeview), you'll be a 2-minute drive from Wrigley Field and 5 minutes from Lake Michigan.

Kitchen

Washer

WINTER DISCOUNTED! Relax with family in a super Lux Custom SFH. West town.

Chicago IL

With a stay at this vacation home in Chicago (West Town), you'll be within a 5-minute drive of United Center and State Street.

Kitchen

Washer

Historic luxury townhouse on Chicago's Gold Coast

Chicago IL

With a stay at this vacation home, you'll be centrally located in Chicago, steps from Michigan Avenue and 8 minutes by foot from Lake Michigan.

Kitchen

Washer

Cozy 3-bedroom house in family-oriented Melrose Park.

Melrose Park IL

Located in Franklin Park, this vacation home is within a 15-minute drive of Donald E. Stephens Convention Center and Allstate Arena.

Hot Tub

Kitchen

Entire 3 Bedroom Cozy Unit

Waukegan IL

With a stay at this vacation home in Waukegan, you'll be a 5-minute drive from Lake Michigan and 9 minutes from Naval Base Great Lakes.

Kitchen

Washer

Urban Farmhouse near O’Hare Airport

Des Plaines IL

When you stay at this vacation home in Des Plaines, you'll be on a river, within a 10-minute drive of Allstate Arena and Donald E. Stephens Convention Center.

Kitchen

Washer

EAST VILLAGE 4-LEVEL-HOUSE WITH 5 BATHS & COVERED ATTACHED GARAGE

Chicago IL

With a stay at this vacation home, you'll be centrally located in Chicago, within a 5-minute drive of United Center and Michigan Avenue.

Kitchen

Washer

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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.