Winthrop Harbor Vacation Packages 2026 from $747

Winthrop Harbor flight + hotel vacation packages

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

Pendry Chicago

Downtown Chicago

Save 100% on your flight

$747

per person

Sep 3 - Sep 6

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.

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$857

per person

Sep 17 - Sep 21

found 1 day ago

Roundtrip flight included

Atlanta (ATL) 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.

Level Chicago - River North

Downtown Chicago

Save 100% on your flight

$775

per person

Sep 13 - Sep 16

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features a gym and a seasonal outdoor pool. WiFi in public areas is free. Self parking, laundry facilities, and concierge services are also on offer.

Omni Chicago Hotel

Downtown Chicago

Save 100% on your flight

$860

per person

Sep 17 - Sep 21

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.

Level Chicago – Old Town

Downtown Chicago

Save 100% on your flight

$778

per person

Sep 13 - Sep 16

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.

Top Winthrop Harbor hotels deals

LA VILLA MOTEL

1401 Sheridan Rd Winthrop Harbor IL

Free Cancellation

Reserve now, pay when you stay

$59 nightly

$69 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

$73 nightly

$85 total

Jun 28 - Jun 29

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

Great Wolf Lodge Illinois

1700 Nations Dr Gurnee IL

$149 nightly

$170 total

Jun 30 - Jul 1

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 2 - Jul 3

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

Best Western Executive Inn Kenosha/Pleasant Prairie

7220 122nd Ave Kenosha WI

Free Cancellation

Reserve now, pay when you stay

$88 nightly

$99 total

Jun 28 - Jun 29

Total with taxes and fees

A casino, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Business travelers can take advantage of the free WiFi in public areas. Enjoy the indoor pool and free perks like buffet breakfast and free self parking.

Pool

Hot Tub

La Quinta Inn & Suites by Wyndham Chicago Gurnee

5688 Northridge Rd Gurnee IL

Free Cancellation

Reserve now, pay when you stay

$73 nightly

$82 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

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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

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.

Spring Bluff Forest Preserve

You can take time to visit Spring Bluff Forest Preserve during your travels to 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 $747. 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.