Deals on vacations and trips to Highland Park

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Price found within the past 48 hours. Click for updated prices.
Staybridge Suites, Lincolnshire by IHG

Staybridge Suites, Lincolnshire by IHG

3 out of 5
Half Day
Save 100% on your flight
Price was $558, price is now $336 per person
$336
per person
Oct 22 - Oct 27
found 16 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Free perks include buffet breakfast, free self parking, and an area shuttle.
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was $1,365, price is now $727 per person
$727
per person
Oct 31 - Nov 5
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. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. A coffee shop, a snack bar/deli, and luggage storage are also on offer.
Chicago Athletic Association, a Hyatt Hotel

Chicago Athletic Association, a Hyatt Hotel

4.5 out of 5
Downtown Chicago
Price was $1,600, price is now $857 per person
$857
per person
Oct 22 - Oct 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This smoke-free hotel's 2 restaurants, 3 bars/lounges, and 24-hour gym are some of the featured amenities. 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.
Staybridge Suites Chicago O'Hare - Rosemont by IHG

Staybridge Suites Chicago O'Hare - Rosemont by IHG

3 out of 5
O'Hare
Save 100% on your flight
Price was $628, price is now $371 per person
$371
per person
Oct 22 - Oct 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Enjoy the free buffet breakfast each morning.
Holiday Inn Chicago O'Hare – Rosemont by IHG

Holiday Inn Chicago O'Hare – Rosemont by IHG

3 out of 5
O'Hare
Save 100% on your flight
Price was $589, price is now $349 per person
$349
per person
Oct 22 - Oct 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
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.

Top Highland Park hotels deals

Claridge House

Claridge House

4 out of 5
1244 N Dearborn Parkway, Chicago, IL
$127 nightly
The price is $150 total per night
$150 total
Aug 24 - Aug 25
Total includes taxes and fees
A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Traveling for business? Take advantage of the 24-hour business center, express check-out, and conference space. You'll appreciate the gym, bar/lounge, and coffee shop.
Spa
Pet friendly
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
$143 nightly
The price is $168 total per night
$168 total
Sep 5 - Sep 6
Total includes 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
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
$179 nightly
The price is $210 total per night
$210 total
Sep 12 - Sep 13
Total includes 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
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave, Rosemont, IL
$143 nightly
The price is $163 total per night
$163 total
Sep 20 - Sep 21
Total includes 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
Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

3.5 out of 5
5440 N River Rd, Rosemont, IL
Free Cancellation
$123 nightly
The price is $140 total per night
$140 total
Sep 1 - Sep 2
Total includes taxes and fees
This hotel features 3 restaurants, an indoor pool, and a gym. Traveling on business? Take advantage of the free WiFi in public areas, express check-in, and free airport shuttle. There's a bar/lounge on site, and a 24-hour front desk and laundry facilities are also provided.
Pool
Free airport shuttle
Holiday Inn Chicago North-Evanston by IHG

Holiday Inn Chicago North-Evanston by IHG

3 out of 5
1501 Sherman Ave, Evanston, IL
$125 nightly
The price is $143 total per night
$143 total
Sep 2 - Sep 3
Total includes taxes and fees
A restaurant and a gym are featured at this hotel. Traveling on business? Take advantage of the business center and free WiFi in public areas. Self parking, a lobby fireplace, and express check-out are also offered.
Free WiFi
Restaurant
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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 featuring cbd, a sporting event and a city

Wrigley Field

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

Wrigley Field
Magnificent Mile - River North showing night scenes, a city and signage

Michigan Avenue

You can enjoy some retail therapy 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
Navy Pier featuring a sunset and rides

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 $336. 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

Photo by Meghan hernandez
Photo by Meghan hernandez
Photo by Tedi Zlat
Photo by Tedi Zlat
Photo by Emily
Photo by Emily
Photo by throwingsofas
Photo by throwingsofas
Photo by throwingsofas
Photo by throwingsofas