Highland Park Vacation Rentals

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Vacation Rentals in Highland Park

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line

Chicago IL

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

ENVITAE Hotel, 4BR Luxury Modern Apartments

Chicago IL

$841 nightly

$1,038 total

Sep 16 - Sep 17

Total with taxes and fees

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

Kitchen

Washer

Charming Home in Portage Park

Chicago IL

With a stay at this vacation home in Chicago (Portage Park), you'll be within a 15-minute drive of Donald E. Stephens Convention Center and Wrigley Field.

Vintage Escape 1BR Two Blocks Away From Beach

Chicago IL

Located in Chicago (Rogers Park), this vacation home is within a 15-minute walk of Lake Michigan and Loyola University Chicago.

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.

Modern 2-Bedroom House with Free Parking and Convenient Location,

Skokie IL

With a stay at this vacation home in Skokie, you'll be within a 10-minute drive of Lake Michigan and Northwestern University.

Charming 3-bedroom house in amazing Chicago

Chicago IL

With a stay at this vacation home in Chicago (Dunning), you'll be within a 10-minute drive of Donald E. Stephens Convention Center and Allstate Arena.

Kitchen

Washer

Pleasant 3-bedroom house with occupied basement separate entrance.

Mundelein IL

Located in Mundelein, this vacation home is within a 10-minute drive of Pine Meadow Golf Club and MainStreet Libertyville.

Washer

Dryer

Your Next Vacation Home

Des Plaines IL

$385 nightly

$412 total

Sep 1 - Sep 2

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.

Lincoln Ave Home By Naval Base!

North Chicago IL

Located in North Chicago, this vacation home is within a 15-minute drive of Lake Michigan and Illinois Beach State Park.

Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars

Chicago IL

With a stay at this vacation home in Chicago (Near North Side), you'll be within a 5-minute drive of Michigan Avenue and Lake Michigan.

Fabulous 3-bedroom townhome with AC in vibrant Chicago

Chicago IL

With a stay at this vacation home in Chicago (Austin), you'll be within a 15-minute drive of United Center and Chicago Riverwalk.

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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.