Highland Park Vacation Packages 2025/2026 from $339

Highland Park flight + hotel vacation packages

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

Hampton Inn Chicago-Carol Stream

Save 100% on your flight

per person

Jul 29 - Aug 3

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features an indoor pool and a 24-hour gym. There's no skimping on freebies - guests receive free on-the-go breakfast, free WiFi, and free self parking. A 24-hour business center, express check-out, and dry cleaning are also on offer.

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

per person

Aug 16 - Aug 21

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

A restaurant is on site and multilingual staff is available around-the-clock at the 24-hour front desk. Unwind with a drink at one of the 2 bars/lounges and enjoy free perks like buffet breakfast and WiFi in public areas. There's a 24-hour gym on site, and a coffee shop and a snack bar/deli are also provided.

Wind Creek Southland Casino and Hotel

East Hazel Crest

Save 100% on your flight

per person

Sep 17 - Sep 21

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (MDW)

This resort features a casino, a full-service spa, and 4 restaurants. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. Relax with a drink at one of the 3 bars/lounges and enjoy perks like free self parking.

Trump International Hotel & Tower Chicago

Downtown Chicago

Save 100% on your flight

per person

Sep 11 - Sep 14

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

A full-service spa, an indoor pool, and a restaurant are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities, kid-friendly dining, and in-room childcare. Enjoy the gym and perks like free WiFi.

The Buckingham Hotel

Downtown Chicago

Save 100% on your flight

per person

Aug 16 - Aug 21

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features a coffee shop, concierge services, and self parking. A 24-hour business center, a snack bar/deli, and luggage storage are also on offer.

Top Highland Park hotels deals

Hilton Chicago O'Hare Airport

O'Hare International Airport, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

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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

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy, Chicago, IL

Free Cancellation

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This hotel features 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

Hyatt Regency O'Hare Chicago

9300 Bryn Mawr Ave, Rosemont, IL

Free Cancellation

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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

5440 N River Rd, Rosemont, IL

Free Cancellation

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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

Chicago Getaway Hostel

616 W Arlington Pl, Chicago, IL

Free Cancellation

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This hostel features a terrace, laundry facilities, and self parking. Enjoy the free continental breakfast each morning. A business center, a garden, and a library are also on offer.

Breakfast included

Air conditioning

Holiday Inn Chicago North-Evanston by IHG

1501 Sherman Ave, Evanston, IL

Free Cancellation

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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

4.5/5(2,128 reviews)

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

Navy Pier

4.5/5(4,870 reviews)

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

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

Michigan Avenue

4.5/5(332 reviews)

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.

Frequently asked questions

How much are vacation packages to Highland Park?

Your travel dreams can come true in Highland Park from just $339. 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.