Deals on vacations and trips to Highland Park

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Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $903, price is now $616 per person
$616
per person
Jul 8 - Jul 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel's 2 restaurants, 2 bars/lounges, and 24-hour gym are some of the featured amenities. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. Self parking, a coffee shop, and a terrace are also offered.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,557, price is now $977 per person
$977
per person
Aug 4 - Aug 8
found 14 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
A seasonal outdoor pool, self parking, and concierge services are featured at this hotel. WiFi in public areas is free. A business center, a picnic area, and luggage storage are also on offer.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,206, price is now $822 per person
$822
per person
Jul 9 - Jul 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This aparthotel features a 24-hour gym and a seasonal outdoor pool. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on site. Enjoy the a rooftop terrace and perks like free WiFi.
Urban Chicago Oasis

Urban Chicago Oasis

2 out of 5
Lakeview
Save 100% on your flight
Price was $1,322, price is now $906 per person
$906
per person
Jul 30 - Aug 2
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features free WiFi in public areas, laundry facilities, and a virtual front desk.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,158, price is now $796 per person
$796
per person
Jul 9 - Jul 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Enjoy the a rooftop terrace and perks like free WiFi. Valet parking, a coffee shop, and a terrace are also offered.

Top Highland Park hotels deals

Courtyard by Marriott Chicago Highland Park/Northbrook

Courtyard by Marriott Chicago Highland Park/Northbrook

3 out of 5
1505 Lake Cook Road Highland Park IL
Free Cancellation
Reserve now, pay when you stay
$107 nightly
The price is $119 total per night
$119 total
Jun 28 - Jun 29
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the 24-hour gym and perks like free self parking.
Pool
Parking included
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
$159 nightly
The price is $181 total per night
$181 total
Jun 28 - Jun 29
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free airport shuttle. Self parking, a coffee shop, and limo/town car service are also offered.
Free airport shuttle
Pet friendly
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Free Cancellation
Reserve now, pay when you stay
$154 nightly
The price is $183 total per night
$183 total
Jun 28 - Jun 29
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and valet parking. A lobby fireplace, luggage storage, and wedding services are also on offer.
Pet friendly
Free WiFi
Holiday Inn Chicago O'Hare – Rosemont by IHG

Holiday Inn Chicago O'Hare – Rosemont by IHG

3 out of 5
6600 Mannheim Road, building 2 Rosemont IL
Free Cancellation
$134 nightly
The price is $152 total per night
$152 total
Jun 28 - Jun 29
Total with taxes and fees
This hotel features an indoor pool, a gym, and a restaurant. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Self parking, a coffee shop, and a grocery/convenience store are also offered.
Pool
Free airport shuttle
Sheraton Suites Chicago O'Hare

Sheraton Suites Chicago O'Hare

3.5 out of 5
6501 N Mannheim Rd Rosemont IL
Free Cancellation
Reserve now, pay when you stay
$137 nightly
The price is $156 total per night
$156 total
Jun 28 - Jun 29
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Self parking, a coffee shop, and a grocery/convenience store are also offered.
Free airport shuttle
Free WiFi
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport Chicago IL
Free Cancellation
Reserve now, pay when you stay
$208 nightly
The price is $245 total per night
$245 total
Jul 3 - Jul 4
Total with taxes and fees
This hotel features 2 restaurants, a bar/lounge, and A 24-hour gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free airport shuttle. You'll appreciate the area shuttle, valet parking, and coffee shop/cafe.
Free airport shuttle
Pet friendly
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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.

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
Soldier Field

Soldier Field

Events center, NFL stadium and historic landmark all in one, this waterfront field is one of Chicago’s most popular destinations.

Soldier Field
Chicago Skyline, Chicago, Illinois shows amazing architecture in panoramic format

Naval Base Great Lakes

After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.

Naval Base Great Lakes

Frequently asked questions

How much are vacation packages to Highland Park?
Your travel dreams can come true in Highland Park from just $616. Our vacation packages include flights and hotels, so booking your trip will be nice and easy. The only thing you'll have to focus on is having a good time.
How long should my Highland Park vacation be?
Many travelers like to spend around 2 nights in Highland Park. But what's right for them mightn't be right for you. Whether you're staying for a matter of days or weeks, you'll love discovering all the incredible things that this destination has to offer.
Where can I get the best vacation package deals for Highland Park?
One word — Travelocity. With as many as 400 air carriers and 1,000,000 properties around the world, it's a breeze to put together a Highland Park package deal that fits your budget.
Why should I book my Highland Park vacation package with Travelocity?
Travel should be about making cherished memories and leaving all your worries behind — which is why we provide you with a team of experts available 24/7 should you need them. On top of that, our Price Match Guarantee ensures you'll always get the best price available on our broad range of destinations. So what are you waiting for? There's no time like the present to lock in that vacation you've always dreamed of.
Can I save money on my Highland Park car rental if I book it with my hotel or flight?
Bundling your car, flight and hotel into a Highland Park vacation package is an excellent way to score an amazing deal. Plus, having your own rental car gives you total freedom to get to all those big-name sights you're eager to see. Located 100 mi from Highland Park, University of Wisconsin-Madison is one attraction that should be on your agenda. Put together a driving playlist and make a day trip of it.
Which airport is best for Highland Park?
O'Hare Intl. Airport (ORD) is one of the top airports for Highland Park. It's situated 15 mi south of the buzzing city center. Other options available to you are Midway Intl. Airport (MDW) (25 mi away from central Highland Park) and General Mitchell Intl. Airport (MKE) (55 mi away from central Highland Park).
What is there to do in Highland Park?
While taking the path less traveled is rewarding, you really shouldn't miss the big sights that make a destination famous. Ravinia Pavilion and Highland Park Country Club are a couple of them in Highland Park.
Where should I stay when visiting Highland Park?
Many visitors choose to check in to the Courtyard by Marriott Chicago Highland Park/Northbrook. It's the perfect base for your Highland Park escape.

Photos of local treasures

Browse Highland Park vacation photos for more inspiration

Daybreak on a Lake Michigan gravel beach at Openlands Lakeshore Preserve, Fort Sheridan, Illinois.
Ft. Sheridan Aerial View 16
Marram grass on a sand dune with clouds at Lake Michigan at Fort Sheridan Forest Preserve in Highland Park, Illinois
Aerial of Lakeshore Development with Pond
Aerial of Lakeshore Development with homes and condos

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