Highland Park Vacation Packages 2025/2026 from $215

Highland Park flight + hotel vacation packages

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

Pendry Chicago

Downtown Chicago

Save 100% on your flight

$215

per person

Jan 22 - Jan 25

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.

The Westin Michigan Avenue Chicago

Downtown Chicago

$526

per person

Dec 23 - Dec 27

found 1 day ago

Roundtrip flight included

Atlanta (ATL) 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 24-hour business center, free WiFi in public areas, and valet parking. You'll appreciate the gym, bar/lounge, and coffee shop.

The Emily Hotel

Downtown Chicago

$918

per person

Feb 2 - Feb 9

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. 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.

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$373

per person

Feb 2 - Feb 9

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Chicago (ORD)

This hotel features 2 bars/lounges and a 24-hour gym. Business travelers can take advantage of the free WiFi in public areas. Enjoy a meal from the restaurant and free buffet breakfast each morning.

Trump International Hotel & Tower Chicago

Downtown Chicago

Save 100% on your flight

$443

per person

Jan 22 - Jan 25

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.

Top Highland Park hotels deals

Hilton Chicago O'Hare Airport

O'Hare International Airport Chicago IL

Free Cancellation

Reserve now, pay when you stay

$230 total

per night

Dec 12 - Dec 13

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

9300 Bryn Mawr Ave Rosemont IL

Free Cancellation

Reserve now, pay when you stay

$135 total

per night

Nov 23 - Nov 24

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

DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove

1200 N Mittel Blvd Wood Dale IL

Free Cancellation

Reserve now, pay when you stay

$99 total

per night

Nov 27 - Nov 28

This hotel features an indoor pool, a 24-hour gym, and a restaurant. Traveling on business? Take advantage of the 24-hour business center and WiFi in public areas. Relax with a drink at the bar/lounge and enjoy perks like free self parking.

Pool

Pet friendly

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL

Free Cancellation

Reserve now, pay when you stay

$169 total

per night

Nov 23 - Nov 24

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

The Chicago Hotel Collection River North

312 W. Chestnut St. Chicago IL

Free Cancellation

Reserve now, pay when you stay

$133 total

per night

Nov 24 - Nov 25

A gym, self parking, and laundry facilities are featured at this hotel. WiFi in public areas is free. A lobby fireplace, express check-out, and luggage storage are also on offer.

Pet friendly

Free WiFi

Holiday Inn Chicago O'Hare – Rosemont by IHG

6600 Mannheim Road, building 2 Rosemont IL

Free Cancellation

$109 total

per night

Nov 27 - Nov 28

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

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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.

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.

McCormick Place

4.5/5(1,805 reviews)

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

Frequently asked questions

How much are vacation packages to Highland Park?

Your travel dreams can come true in Highland Park from just $215. 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.