Deals on vacations and trips to Winthrop Harbor

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Winthrop Harbor flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $669, price is now $363 per person
$363
per person
Nov 7 - Nov 9
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.
The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago

4.5 out of 5
Downtown Chicago
Price was $1,560, price is now $638 per person
$638
per person
Dec 23 - Dec 28
found 24 hours 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. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. You'll appreciate the gym, bar/lounge, and coffee shop.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,115, price is now $633 per person
$633
per person
Dec 13 - Dec 20
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.
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,181, price is now $712 per person
$712
per person
Dec 13 - Dec 20
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.
Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,474, price is now $894 per person
$894
per person
Nov 25 - Dec 2
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.

Top Winthrop Harbor hotels deals

Motel Sun Inn

Motel Sun Inn

2.5 out of 5
301 Sheridan Road, Winthrop Harbor, IL
Free Cancellation
Reserve now, pay when you stay
$59 nightly
The price is $68 total per night
$68 total
Oct 6 - Oct 7
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

LA VILLA MOTEL

2 out of 5
1401 Sheridan Rd, Winthrop Harbor, IL
Free Cancellation
$60 nightly
The price is $69 total per night
$69 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
Hotel Indigo Chicago-Vernon Hills by IHG

Hotel Indigo Chicago-Vernon Hills by IHG

3.5 out of 5
450 N Milwaukee Ave, Vernon Hills, IL
Free Cancellation
$113 nightly
The price is $125 total per night
$125 total
Oct 12 - Oct 13
Total with taxes and fees
This hotel features a restaurant, a 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
Sonesta ES Suites Chicago Waukegan Gurnee

Sonesta ES Suites Chicago Waukegan Gurnee

3 out of 5
1440 S White Oak Dr, Waukegan, IL
Free Cancellation
Reserve now, pay when you stay
$110 nightly
The price is $123 total per night
$123 total
Oct 12 - Oct 13
Total with taxes and fees
This hotel features a 24-hour gym and a seasonal outdoor pool. 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 continental breakfast and free self parking.
Pool
Hot Tub
DoubleTree by Hilton Libertyville - Mundelein

DoubleTree by Hilton Libertyville - Mundelein

4 out of 5
510 E IL Route 83, Mundelein, IL
Free Cancellation
Reserve now, pay when you stay
$110 nightly
The price is $122 total per night
$122 total
Oct 19 - Oct 20
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

La Quinta Inn & Suites by Wyndham Chicago Gurnee

3 out of 5
5688 Northridge Rd, Gurnee, IL
Free Cancellation
Reserve now, pay when you stay
$76 nightly
The price is $85 total per night
$85 total
Oct 7 - Oct 8
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 Beach

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

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.

Spring Bluff Forest Preserve

Frequently asked questions

How much are vacation packages to Winthrop Harbor?
Your vacation dreams can be realized in Winthrop Harbor from an impressive $363. 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.

Photos of local treasures

Browse Winthrop Harbor vacation photos for more inspiration