Highland Park Vacation Rentals

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Vacation Rentals in Highland Park

AeroStay Retreat – 4BR Home Near O’Hare Airport!

Wood Dale IL

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

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Washer

Gilded Age Gold Coast Mansion with Parking, Deck, Fireplaces

Chicago IL

With a stay at this vacation home in Chicago (Downtown Chicago), you'll be within a 5-minute walk of Michigan Avenue and State Street.

Your Next Vacation Home

Des Plaines IL

$282 nightly

$302 total

Jan 5 - Jan 6, 2026

Total with taxes and fees

With a stay at this vacation home in Des Plaines (Oakton), you'll be a 3-minute drive from Allstate Arena and 7 minutes from Donald E. Stephens Convention Center.

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Washer

The Nicest House on VRBO in Chicago? Perhaps.. Custom Built 5 bdrm in 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.

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Washer

Family frndly TwnHm by navy base

Waukegan IL

With a stay at this vacation home in Waukegan, you'll be a 2-minute drive from Lake Michigan and 7 minutes from Naval Base Great Lakes.

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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

Beautiful Updated Home near Great Lakes Naval Base

Waukegan IL

With a stay at this vacation home in Waukegan, you'll be a 3-minute drive from Lake Michigan and 8 minutes from Naval Base Great Lakes.

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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.

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Breathtaking home close to Schaumburg, Chicago

Palatine IL

With a stay at this vacation home in Schaumburg, you'll be within a 5-minute drive of Schaumburg Convention Center and Woodfield Mall.

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Charming 3-bedroom house in Grayslake

Grayslake IL

With a stay at this vacation home in Grayslake (Gages Lake), you'll be within a 15-minute drive of Naval Base Great Lakes and Gurnee Mills.

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Updated Forest Park 3 BR Bungalow

Forest Park IL

With a stay at this vacation home in Forest Park, you'll be within a 15-minute drive of United Center and Millennium Park.

Paradise 4BR w/ Pool & Games

Schaumburg IL

With a stay at this vacation home in Schaumburg, you'll be within a 15-minute drive of Woodfield Mall and Schaumburg Convention Center.

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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.