Highland Park Vacation Packages 2026 from $399

Highland Park flight + hotel vacation packages

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

Pendry Chicago

Downtown Chicago

$399

per person

Mar 13 - Mar 15

found 1 day ago

Roundtrip flight included

Charlotte (CLT) 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.

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$472

per person

Mar 13 - Mar 15

found 1 day ago

Roundtrip flight included

Charlotte (CLT) 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.

Swissotel - Chicago

Downtown Chicago

Save 100% on your flight

$402

per person

Feb 13 - Feb 17

found 1 day ago

Roundtrip flight included

Charlotte (CLT) to Chicago (ORD)

This hotel features 2 bars/lounges and a 24-hour gym. Traveling on business? Take advantage of the business center, express check-in, and valet parking. A restaurant, a 24-hour front desk, and laundry facilities are also provided.

The Emily Hotel

Downtown Chicago

Save 100% on your flight

$439

per person

Mar 13 - Mar 15

found 1 day ago

Roundtrip flight included

Charlotte (CLT) 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.

Trump International Hotel & Tower Chicago

Downtown Chicago

Save 100% on your flight

$638

per person

Feb 4 - Feb 7

found 1 day ago

Roundtrip non-stop flight included

Charlotte (CLT) 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

$196 nightly

$230 total

Jan 16 - Jan 17, 2026

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

Hyatt Regency O'Hare Chicago

9300 Bryn Mawr Ave Rosemont IL

Free Cancellation

Reserve now, pay when you stay

$110 nightly

$125 total

Dec 25 - Dec 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.

Free airport shuttle

Pet friendly

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

5440 N River Rd Rosemont IL

Free Cancellation

$101 nightly

$115 total

Dec 28 - Dec 29

Total with taxes and fees

This hotel features 3 restaurants, an indoor pool, and a gym. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, 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

The Chicago Hotel Collection River North

312 W. Chestnut St. Chicago IL

Free Cancellation

Reserve now, pay when you stay

$99 nightly

$116 total

Dec 25 - Dec 26

Total with taxes and fees

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

Viceroy Chicago

1118 North State Street Chicago IL

Free Cancellation

Reserve now, pay when you stay

$219 nightly

$257 total

Jan 20 - Jan 21, 2026

Total with taxes and fees

This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. Enjoy the seasonal outdoor pool and conveniences like a 24-hour front desk and laundry facilities.

Pool

Pet friendly

Holiday Inn Chicago O'Hare – Rosemont by IHG

6600 Mannheim Road, building 2 Rosemont IL

Free Cancellation

$115 nightly

$131 total

Dec 25 - Dec 26

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

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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

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.

Wrigley Field

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

Navy Pier

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

Frequently asked questions

How much are vacation packages to Highland Park?

Your travel dreams can come true in Highland Park from just $399. 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.