Winthrop Harbor Vacation Packages 2026 from $559

Name: Hotel Indigo Chicago-Vernon Hills by IHG
Price range: $118 total

Winthrop Harbor flight + hotel vacation packages

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

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$559

per person

Sep 4 - Sep 7

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 Fulton Market

Downtown Chicago

Save 100% on your flight

$696

per person

Aug 28 - Sep 1

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.

Hotel Felix River North/Magnificent Mile

Downtown Chicago

Save 100% on your flight

$718

per person

Jul 23 - Jul 27

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.

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

Save 100% on your flight

$794

per person

Sep 4 - Sep 7

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel's 2 restaurants, 2 bars/lounges, and 24-hour gym are some of the featured amenities. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. Self parking, a coffee shop, and a terrace are also offered.

The Emily Hotel

Downtown Chicago

Save 100% on your flight

$1,115

per person

Jul 30 - Aug 3

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, laundry service, and valet parking. A coffee shop, a snack bar/deli, and luggage storage are also on offer.

Top Winthrop Harbor hotels deals

Motel Sun Inn

301 Sheridan Road Winthrop Harbor IL

Free Cancellation

Reserve now, pay when you stay

$77 nightly

$89 total

Jun 15 - Jun 16

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

LA VILLA MOTEL

1401 Sheridan Rd Winthrop Harbor IL

Free Cancellation

$59 nightly

$68 total

Jun 23 - Jun 24

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

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 17 - Jun 18

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

$106 nightly

$118 total

Jul 13 - Jul 14

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

Days Inn by Wyndham Waukegan

630 N Green Bay Road Waukegan IL

Free Cancellation

Reserve now, pay when you stay

$78 nightly

$88 total

Jun 15 - Jun 16

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.

Breakfast included

Pet friendly

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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 $559. 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.