Highland Park Holidays from £1,007

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Your Highland Park Holiday

Planning your next big adventure is a piece of cake with a Highland Park holiday package. The neighbourhood of Riverwoods, which is great for nature, makes a superb base to uncover the marvels of this unique city. If sightseeing is part of the plan during your trip to Highland Park, check out well-known attractions like Chicago Botanic Garden, Lake Forest College and Northbrook Sports Complex. Whoever you're escaping with and whatever you plan to spend, your dream Highland Park holiday is just clicks away with Expedia.

Top Highland Park Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was £1,321, price is now £1,007 per person
£1,007
per person
9 Jul - 15 Jul
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
8.2/10 Very Good! (2,636 reviews)
The staff were extremely impressed and helpful. Help me with restaurant choices, where to go for tours. Only thing I regretted was not packing the proper clothes for the chance of weather. It was my personal birthday present to me and I did enjoyed myself.

Reviewed on 24 Apr 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was £1,810, price is now £1,241 per person
£1,241
per person
9 Jul - 15 Jul
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (455 reviews)
Great staff, full kitchen and living room, good location, friendly people, safe. I would stay here again.

Reviewed on 23 Apr 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was £1,793, price is now £1,244 per person
£1,244
per person
16 Jun - 21 Jun
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9/10 Wonderful! (3,280 reviews)
Really good spot and location. Staff was super helpful and nice.

Reviewed on 22 Apr 2026

Hilton Chicago

Hilton Chicago

4 out of 5
Downtown Chicago
Price was £1,495, price is now £1,125 per person
£1,125
per person
9 Jul - 15 Jul
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
8.6/10 Excellent! (2,742 reviews)
Staff were nice. Hotel was at maximum capacity per security and it just felt overwhelming and claustrophobic at times.

Reviewed on 22 Apr 2026

Holiday Inn Express Chicago - Magnificent Mile by IHG

Holiday Inn Express Chicago - Magnificent Mile by IHG

2.5 out of 5
Downtown Chicago
Price was £1,431, price is now £1,113 per person
£1,113
per person
9 Jul - 15 Jul
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
8.4/10 Very Good! (1,018 reviews)
Clean comfortable room , staff helpful, breakfast standard and location good

Reviewed on 24 Apr 2026

Highland Park Essential Information

Language
English
Currency
U.S dollars
Closest Airport
O'Hare Intl. Airport (ORD)
Population
29,700
Max Temp Winter
-1.11ºC
Max Temp Summer
24ºC
Top Sights
Marriott Theatre, Kohl Childrens Museum and North Shore Centre for the Performing Arts

Top hotels in Highland Park

The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is £114 per night from 27 Apr to 28 Apr
£114
27 Apr - 28 Apr
includes taxes & fees
8.2/10 Very Good! (1,383 reviews)
Bathrooms need some updating.

Reviewed on 24 Apr 2026

The Chicago Hotel Collection Ambassador Gold Coast
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
The price is £151 per night from 1 May to 2 May
£151
1 May - 2 May
includes taxes & fees
8.8/10 Excellent! (2,510 reviews)
Wonderful room and great stay

Reviewed on 23 Apr 2026

Hyatt Regency O'Hare Chicago
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
The price is £192 per night from 23 May to 24 May
£192
23 May - 24 May
includes taxes & fees
8.4/10 Very Good! (2,270 reviews)
Restaurant is good. Easy access

Reviewed on 24 Apr 2026

Hilton Chicago O'Hare Airport
See all 2,687 properties in Highland Park
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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Family Friendly Holidays

Popular places to visit

Wrigley Field

Wrigley Field

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Navy Pier

Navy Pier

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier
Scene of Chicago street bridge with traffic among modern buildings of Downtown Chicago at Michigan avenue in Chicago, Illinois, United States, Business and Modern Transportation concept

Michigan Avenue

You can find the perfect gifts to bring home when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue

What to do in Highland Park

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£20
per adult
88% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

£32
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

£30
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See all activities in Highland Park

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.