Winthrop Harbor Vacation Packages 2026 from $228

Winthrop Harbor flight + hotel vacation packages

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

Harrah's Joliet Casino & Hotel - A Caesars Rewards Destination

Save 100% on your flight

$228

per person

May 20 - May 23

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features 3 restaurants, a bar/lounge, and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. A coffee shop, express check-out, and luggage storage are also on offer.

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$584

per person

May 19 - May 23

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.

Fairmont Chicago at Millennium Park

Downtown Chicago

Save 100% on your flight

$951

per person

May 21 - May 26

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. Families will appreciate the onsite laundry facilities and in-room childcare. Relax with a drink at one of the 2 bars/lounges and get perks like free WiFi.

Level Chicago – Old Town

Downtown Chicago

Save 100% on your flight

$559

per person

Jun 26 - Jun 29

found 22 hours 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.

Eurostars Magnificent Mile

Downtown Chicago

Save 100% on your flight

$558

per person

May 22 - May 26

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

A full-service spa and a gym are featured at this boutique hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. There's a sauna on site, and a 24-hour front desk and express check-out are also provided.

Top Winthrop Harbor hotels deals

Great Wolf Lodge Illinois

1700 Nations Dr Gurnee IL

Free Cancellation

Reserve now, pay when you stay

$149 nightly

$170 total

Apr 19 - Apr 20

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.

Days Inn by Wyndham Waukegan

630 N Green Bay Road Waukegan IL

Free Cancellation

Reserve now, pay when you stay

$62 nightly

$70 total

May 4 - May 5

Total with taxes and fees

This motel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. A business center, a coffee shop, and laundry facilities are also on offer.

Days Inn by Wyndham Pleasant Prairie Kenosha

7540 118th Ave Pleasant Prairie WI

Free Cancellation

Reserve now, pay when you stay

$72 nightly

$82 total

May 3 - May 4

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free full breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the business center and free internet in public areas. There's a gym on site, and a 24-hour front desk and a fireplace in the lobby are also provided.

La Quinta Inn & Suites by Wyndham Chicago Gurnee

5688 Northridge Rd Gurnee IL

Free Cancellation

Reserve now, pay when you stay

$62 nightly

$69 total

Apr 26 - Apr 27

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.

Hotel Indigo Chicago-Vernon Hills by IHG

450 N Milwaukee Ave Vernon Hills IL

Free Cancellation

$98 nightly

$109 total

Apr 27 - Apr 28

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.

Comfort Suites Grayslake near Libertyville North

1775 East Belvidere Road Grayslake IL

Free Cancellation

$95 nightly

$105 total

May 10 - May 11

Total with taxes and fees

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 hot tub and free perks like buffet breakfast and free self parking.

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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

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

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.

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 $228. 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.