Winthrop Harbor Holidays

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    Save up to €185 when you book a flight and hotel together*
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Top Flight + Hotel Deals in Winthrop Harbor

Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Chicago River North
Trump International Hotel & Tower Chicago
The Emily Hotel
Level Chicago – Old Town
Pendry Chicago

Top hotels in Winthrop Harbor

Motel Sun Inn

Motel Sun Inn

2.5 out of 5
301 Sheridan Road, Winthrop Harbor, IL
Fully refundableReserve now, pay when you stay
The price is €59 per night from 2 Sept to 3 Sept
€59
2 Sept - 3 Sept
includes taxes & fees
6.6/10 (252 reviews)
"Pleasantly surprised."

Reviewed on 17 Aug 2025

Motel Sun Inn
LA VILLA MOTEL

LA VILLA MOTEL

2 out of 5
1401 Sheridan Rd, Winthrop Harbor, IL
Fully refundable
The price is €61 per night from 26 Aug to 27 Aug
€61
26 Aug - 27 Aug
includes taxes & fees
6.4/10 (45 reviews)
"Good"

Reviewed on 13 Aug 2025

LA VILLA MOTEL
DoubleTree by Hilton Libertyville - Mundelein

DoubleTree by Hilton Libertyville - Mundelein

4 out of 5
510 E IL Route 83, Mundelein, IL
Fully refundableReserve now, pay when you stay
The price is €104 per night from 1 Sept to 2 Sept
€104
1 Sept - 2 Sept
includes taxes & fees
8.4/10 Very Good! (1,002 reviews)
"Nice place ,clean , good service"

Reviewed on 16 Aug 2025

DoubleTree by Hilton Libertyville - Mundelein
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.

Frequently asked questions

How much does a Winthrop Harbour holiday package cost?
You'll find cheap prices from €843 on Expedia for your Winthrop Harbour getaway. However, factors like the hotel choice, length of stay and season will determine how much your holiday to Winthrop Harbour costs.
What are the cheapest months to go to Winthrop Harbour?
If you're looking to score a cheap Winthrop Harbour holiday package, consider travelling in January, February and March. You'll generally find lower rates on hotels and airfares during these quieter months — perfect for a budget-friendly break.
How many days is enough for Winthrop Harbour?
Typically, a handful of days is enough to see the major attractions during your Winthrop Harbour holiday. However, if you'd like to have some time to kick back or go on day trips, think about extending your trip.
How to find the best Winthrop Harbour package deals?
Landing a cheap Winthrop Harbour package deal is easy with Expedia. After you've entered your destination and travel dates under our "Packages" tab, set your budget, apply a couple of filters and browse what's available. You can tweak your search by "Amenities," "Property type," "Popular locations" and more. Sort the results by "Price: low to high" to view the most economical Winthrop Harbour package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book a Winthrop Harbour holiday as a package?
An Expedia holiday package could save you hundreds of dollars when compared to arranging flights and accommodation individually. Better still, you can customise your Winthrop Harbour trip to fit your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Explore our bundles to see how much you can save.
When to book a holiday package to Winthrop Harbour?
If you're planning an impromptu Winthrop Harbour getaway, browse our last-minute deals that can be booked up to one week before you take off. Don't want to leave things to the last minute? You can score sensational deals on your flights and hotels by booking ahead.
How to plan a trip to Winthrop Harbour?

  1. Choose your travel dates: The things you'd like to do in Winthrop Harbour and your preferred season can help you decide when to go.
  2. Calculate your budget: Ensure you have enough money to pay for everything from transportation and dining out to flights and experiences. Your hotel will likely be the largest expense during your trip to Winthrop Harbour.
  3. Set the duration of your trip: Start by compiling a list of the sights and activities you want to experience in Winthrop Harbour. Then, estimate how long you'll need at each, including any travel time.
  4. Bundle your airfare and accommodation: After you've settled on your dates and duration, book the right Winthrop Harbour holiday package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.