Winthrop Harbor Vacation Packages 2026 from $375

Winthrop Harbor flight + hotel vacation packages

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

Hampton Inn & Suites Chicago Medical District UIC

Near West Side

Save 100% on your flight

$375

per person

Sep 14 - Sep 16

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the free full breakfast each morning.

Level Chicago – Old Town

Downtown Chicago

Save 100% on your flight

$927

per person

Sep 3 - Sep 8

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This aparthotel features a 24-hour gym and a seasonal outdoor pool. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on site. Enjoy the a rooftop terrace and perks like free WiFi.

Hotel Felix River North/Magnificent Mile

Downtown Chicago

Save 100% on your flight

$485

per person

Aug 22 - Aug 26

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features a 24-hour gym and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. A lobby fireplace, a communal living room, and express check-out are also on offer.

LondonHouse Chicago, Curio Collection by Hilton

Downtown Chicago

Save 100% on your flight

$658

per person

Aug 22 - Aug 26

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

A full-service spa, 2 restaurants, and a gym are all featured at this luxury hotel. Relax with a drink at one of the 2 bars/lounges and get perks like free WiFi. A business center, a terrace, and dry cleaning are also on offer.

Omni Chicago Hotel

Downtown Chicago

Save 100% on your flight

$502

per person

Aug 28 - Aug 31

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, express check-out, and valet parking. There's in-room fitness on site, and concierge services and wedding services are also offered.

Top Winthrop Harbor hotels deals

LA VILLA MOTEL

1401 Sheridan Rd Winthrop Harbor IL

Free Cancellation

Reserve now, pay when you stay

$54 nightly

$63 total

Jul 9 - Jul 10

Total with taxes and fees

Staff at the 24-hour front desk can provide around-the-clock assistance. Take advantage of the free self parking.

Parking included

Free WiFi

Motel Sun Inn

301 Sheridan Road Winthrop Harbor IL

Free Cancellation

Reserve now, pay when you stay

$77 nightly

$89 total

Jun 21 - Jun 22

Total with taxes and fees

Free self parking is available and the motel's front desk is staffed around-the-clock. WiFi in public areas is free. A garden is also provided.

Parking included

Free WiFi

DoubleTree by Hilton Libertyville - Mundelein

510 E IL Route 83 Mundelein IL

Free Cancellation

Reserve now, pay when you stay

$108 nightly

$120 total

Jun 28 - Jun 29

Total with taxes and fees

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

Pool

Pet friendly

Great Wolf Lodge Illinois

1700 Nations Dr Gurnee IL

$179 nightly

$204 total

Jun 22 - Jun 23

Total with taxes and fees

Free water park access, 5 restaurants, and 6 indoor pools are all featured at this smoke-free resort. Bring the family and enjoy the lazy river, bowling alley, and mini golf. Enjoy the seasonal outdoor pool and visit the 2 bars/lounges and poolside bar for drinks.

Pool

Restaurant

Hotel Indigo Chicago-Vernon Hills by IHG

450 N Milwaukee Ave Vernon Hills IL

Free Cancellation

$114 nightly

$127 total

Jul 1 - Jul 2

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 24-hour business center and free WiFi in public areas. Free self parking, a snack bar/deli, and express check-in are also offered.

Pet friendly

Parking included

La Quinta Inn & Suites by Wyndham Chicago Gurnee

5688 Northridge Rd Gurnee IL

Free Cancellation

Reserve now, pay when you stay

$80 nightly

$89 total

Jul 5 - Jul 6

Total with taxes and fees

This hotel features an indoor pool and a hot tub. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.

Pool

Hot Tub

Don't see what you're looking for?

See all available properties in Winthrop Harbor

View all properties

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

North Point Marina Beach

Why not spend a lazy afternoon at North Point Marina Beach during your trip to Winthrop Harbor? While you're in the area, stroll along the beaches.

North Point Marina

Explore the waterfront in Winthrop Harbor with a trip to North Point Marina. While you're in the area, stroll along the beaches.

Winthrop Harbor Village Hall

After visiting Winthrop Harbor Village Hall, make a plan to see the other sights and activities in Winthrop Harbor. While you're in the area, stroll along the beaches.

Frequently asked questions

How much are vacation packages to Winthrop Harbor?

Your vacation dreams can be realized in Winthrop Harbor from an impressive $375. Vacation packages include flights and hotels, so organizing your itinerary will be nice and easy. The only thing you'll need to worry about is having an incredible time.

How long should my Winthrop Harbor vacation be?

On average, visitors stay 2 nights in Winthrop Harbor. Although, that mightn't be anywhere near enough for you. If you hope to explore some of the area's off-the-beaten-path treasures, how about adding another couple of nights to your itinerary?

Where can I get the best vacation package deals for Winthrop Harbor?

You'll come across a tempting selection of Winthrop Harbor package deals on Travelocity. With as many as 400 airlines and 1,000,000 properties around the globe, piecing together the ultimate getaway will be a breeze.

Why should I purchase my Winthrop Harbor vacation bundle with Travelocity?

With exceptional service, customer support available 24/7 and some of the most incredible escapes on offer, you'll never roam alone. And if you happen to find a better price, we'll match it. That's our Price Match Guarantee.

Can I save money on my Winthrop Harbor car rental if I book it with my hotel or flight?

Combining your hotel, flight and car into a Winthrop Harbor vacation package is a surefire way to land the best deal. Plus, having your own rental car gives you absolute freedom to find your way to all the landmarks you're eager to see. Situated 40 mi from Winthrop Harbor, Wrigley Field 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 Winthrop Harbor?

O'Hare Intl. Airport (ORD) is a main hub. You'll find it approximately 35 mi south of Winthrop Harbor. Your other options are Midway Intl. Airport (MDW) (50 mi away from central Winthrop Harbor) and General Mitchell Intl. Airport (MKE) (35 mi away from central Winthrop Harbor).

Where should I stay when visiting Winthrop Harbor?

Many visitors opt to stay at the Motel Sun Inn. It's sure to be a good base for your Winthrop Harbor escape.