Deals on vacations and trips to Highland Park

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Price found within the past 48 hours. Click for updated prices.
Dorothy's

Dorothy's

2 out of 5
Lakeview
Price was $745, price is now $536 per person
$536
per person
Jul 17 - Jul 20
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Chicago (ORD)
Free WiFi in public areas, a communal living room, and luggage storage are available at this bed & breakfast. Enjoy the free continental breakfast each morning. A virtual front desk are provided for your convenience.
JW Marriott Chicago

JW Marriott Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,136, price is now $759 per person
$759
per person
Aug 6 - Aug 10
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the business center, express check-in, and valet parking. You'll appreciate the indoor pool, bar/lounge, and laundry facilities.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,162, price is now $782 per person
$782
per person
Aug 3 - Aug 6
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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.
Chicago Athletic Association, a Hyatt Hotel

Chicago Athletic Association, a Hyatt Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $830, price is now $604 per person
$604
per person
Aug 3 - Aug 6
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
This luxury hotel features 4 restaurants, a bar/lounge, and a 24-hour gym. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and valet parking. There's a rooftop terrace on site, and a 24-hour front desk and a coffee shop are also provided.
Urban Chicago Oasis

Urban Chicago Oasis

2 out of 5
Lakeview
Save 100% on your flight
Price was $1,650, price is now $1,212 per person
$1,212
per person
Jul 16 - Jul 20
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Chicago (ORD)
This hotel features free WiFi in public areas, laundry facilities, and a virtual front desk.

Top Highland Park hotels deals

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
$231 nightly
The price is $271 total per night
$271 total
Jun 20 - Jun 21
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.
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
$146 nightly
The price is $174 total per night
$174 total
Jun 3 - Jun 4
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.
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
Free Cancellation
Reserve now, pay when you stay
$169 nightly
The price is $193 total per night
$193 total
May 25 - May 26
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.
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
$116 nightly
The price is $132 total per night
$132 total
May 27 - May 28
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.
Hyatt Place Chicago/O'Hare Airport

Hyatt Place Chicago/O'Hare Airport

3 out of 5
6810 Mannheim Rd Rosemont IL
Free Cancellation
Reserve now, pay when you stay
$129 nightly
The price is $147 total per night
$147 total
May 25 - May 26
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, free WiFi in public areas, and free airport shuttle. Enjoy the 24-hour gym and free perks like buffet breakfast and a bus station shuttle.
Pool
Breakfast included
Marriott Chicago O'Hare

Marriott Chicago O'Hare

3.5 out of 5
8535 West Higgins Road Chicago IL
Free Cancellation
Reserve now, pay when you stay
$169 nightly
The price is $199 total per night
$199 total
Jun 7 - Jun 8
Total with taxes and fees
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free airport shuttle. There's an indoor pool on site, and a 24-hour front desk and a coffee shop are also provided.
Pool
Free airport shuttle
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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
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
Navy Pier

Navy Pier

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

Navy Pier

Frequently asked questions

How much are vacation packages to Highland Park?
Your travel dreams can come true in Highland Park from just $536. 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

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
Aerial of Lakeshore Development

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