Winthrop Harbor Vacation Packages 2026 from $654

Winthrop Harbor flight + hotel vacation packages

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

Level Chicago Fulton Market

Downtown Chicago

Save 100% on your flight

$654

per person

Nov 20 - Nov 24

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, a business center, and a picnic area are also offered.

Four Seasons Hotel Chicago

Downtown Chicago

Save 100% on your flight

$791

per person

Dec 23 - Dec 26

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 smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. You'll appreciate the 24-hour gym, bar/lounge, and laundry facilities.

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

Save 100% on your flight

$694

per person

Dec 25 - Dec 28

found 1 day ago

Roundtrip flight included

Dallas (DFW) 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.

Level Chicago – Old Town

Downtown Chicago

Save 100% on your flight

$705

per person

Nov 20 - Nov 24

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.

Trump International Hotel & Tower Chicago

Downtown Chicago

Save 100% on your flight

$823

per person

Nov 13 - Nov 16

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 Winthrop Harbor hotels deals

LA VILLA MOTEL

1401 Sheridan Rd Winthrop Harbor IL

Free Cancellation

$61 nightly

$71 total

Oct 14 - Oct 15

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

$66 nightly

$77 total

Nov 1 - Nov 2

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

$106 nightly

$117 total

Oct 18 - Oct 19

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

La Quinta Inn & Suites by Wyndham Chicago Gurnee

5688 Northridge Rd Gurnee IL

Free Cancellation

Reserve now, pay when you stay

$64 nightly

$71 total

Nov 2 - Nov 3

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 buffet breakfast and free self parking.

Pool

Hot Tub

Great Wolf Lodge Illinois

1700 Nations Dr Gurnee IL

$155 nightly

$177 total

Oct 8 - Oct 9

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

The Inn on Sheridan

2723 Sheridan Rd Zion IL

Free Cancellation

Reserve now, pay when you stay

$70 nightly

$77 total

Nov 2 - Nov 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. Guests will appreciate freebies like buffet breakfast and free self parking.

Breakfast included

Parking included

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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.

Stay near popular Winthrop Harbor attractions

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.

See properties

Frequently asked questions

How much are vacation packages to Winthrop Harbor?

Your vacation dreams can be realized in Winthrop Harbor from an impressive $654. 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.