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Highland Park Holiday Rentals
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Holiday Rentals in Highland Park
4-Bedroom Penthouse w/ 2 Large Balconies & Rooftop
4-Bedroom Penthouse w/ 2 Large Balconies & Rooftop
10.0 out of 10, Exceptional, (21)
Ground Floor Studios in Chicago by 747 Lofts
Ground Floor Studios in Chicago by 747 Lofts
10.0 out of 10, Exceptional, (7)
The price is HK$786
HK$1,332 total
includes taxes & fees
27 May - 28 May
NEW LUXURY CONDO WITH PATIO DECK
NEW LUXURY CONDO WITH PATIO DECK
10.0 out of 10, Exceptional, (125)
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3BD/2BA DUAL LEVEL WITH FAMILY ROOM KING BED/LAUNDRY ROOM- IDEAL 4 EXTENDED STAY
3BD/2BA DUAL LEVEL WITH FAMILY ROOM KING BED/LAUNDRY ROOM- IDEAL 4 EXTENDED STAY
10.0 out of 10, Exceptional, (55)
Game room/King Bed /Wi-Fi/Deck + Fire Pit
Game room/King Bed /Wi-Fi/Deck + Fire Pit
10.0 out of 10, Exceptional, (13)
The price is HK$1,718
HK$3,453 total
includes taxes & fees
23 May - 24 May
Your Next Vacation Home
Your Next Vacation Home
10.0 out of 10, Exceptional, (9)
The price is HK$1,522
HK$2,648 total
includes taxes & fees
3 Jun - 4 Jun
Roscoe Village Inn | Guesthouse | Walk to Chicago's Wrigley Field
Roscoe Village Inn | Guesthouse | Walk to Chicago's Wrigley Field
10.0 out of 10, Exceptional, (145)
The Lake House-2br/2bth - 50 steps from the beach!
The Lake House-2br/2bth - 50 steps from the beach!
10.0 out of 10, Exceptional, (19)
Walking distance to restaurants, shops and Lake Michigan,
Walking distance to restaurants, shops and Lake Michigan,
9.8 out of 10, Exceptional, (157)
Wrigley/Southport Corridor Garden Oasis +parking!
Wrigley/Southport Corridor Garden Oasis +parking!
9.8 out of 10, Exceptional, (38)
Stay in “STYLE” Apartment, close to CHI downtown
Stay in “STYLE” Apartment, close to CHI downtown
9.8 out of 10, Exceptional, (61)
Modern & Stylish West Town Loft with Pool Table (Pets Allowed)
Modern & Stylish West Town Loft with Pool Table (Pets Allowed)
9.8 out of 10, Exceptional, (8)
Stunning 3 BR in prime Chicago location
Stunning 3 BR in prime Chicago location
9.8 out of 10, Exceptional, (45)
Complete Furnished & Modern 1BR Apt
Complete Furnished & Modern 1BR Apt
9.8 out of 10, Exceptional, (6)
The price is HK$740
HK$1,450 total
includes taxes & fees
27 May - 28 May
Walking distance to restaurants, shops and Lake Michigan,
Walking distance to restaurants, shops and Lake Michigan,
9.8 out of 10, Exceptional, (178)
Beautiful, Remodeled Penthouse Unit in Old Town!
Beautiful, Remodeled Penthouse Unit in Old Town!
9.6 out of 10, Exceptional, (7)
Hidden East Village Gem
Hidden East Village Gem
9.6 out of 10, Exceptional, (20)
Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families
Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families
9.6 out of 10, Exceptional, (8)
The price is HK$944
HK$1,842 total
includes taxes & fees
26 May - 27 May
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars
9.4 out of 10, Exceptional, (70)
Prime location Historic Chicago Townhouse
Prime location Historic Chicago Townhouse
9.4 out of 10, Exceptional, (59)
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.
Other types of properties in Highland Park you may be interested in
Ambassador Chicago, part of JdV by Hyatt
Ambassador Chicago, part of JdV by Hyatt
8.8 out of 10, Excellent, (1003)
The price is HK$1,374
HK$1,768 total
includes taxes & fees
28 May - 29 May
Claridge House
Claridge House
8.4 out of 10, Very good, (1100)
The price is HK$1,005
HK$1,409 total
includes taxes & fees
27 May - 28 May
Marriott Chicago O'Hare
Marriott Chicago O'Hare
8.2 out of 10, Very good, (1003)
The price is HK$1,318
HK$1,547 total
includes taxes & fees
23 May - 24 May
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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Frequently asked questions
Recent reviews of Highland Park propertiesExpedia verified reviews
5/5 Excellent
"This stay was everything that I needed after returning back to the States from a 3-week trip to Europe. The hotel shuttle was convenient and faster than what I read in other reviews. My bed was very comfortable and the breakfast was good. They even had room service, but after 20 hours of traveling, I skipped dinner and just showered and went to bed.
I had read a review from another woman staying there alone where she was made to feel uncomfortable by a man claiming to be maintenence trying to come into her room. This scared me and should be something that all women traveling alone should be wary of, so I want to note here that nothing like this happened to me during my 1-night stay. My room was on the first floor facing the parking lot, so I immediately shut the curtains so nobody could see in. The room had both a deadbolt and a door stopper thing that wouldn't let it open more than an inch even if someone were able to get past the deadbolt. So fortunately nobody tried to get in my room, and even if they did, I trusted that the door could not be broken into. "
A verified traveller stayed at Best Western At O'Hare
Posted 4 hours ago
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