Winthrop Harbor Trip

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Top Winthrop Harbor Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
16 Aug - 21 Aug
found 1 day ago
Return flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (1,755 reviews)
beautiful hotel, friendly and helpful staff.

Reviewed on 2 Jul 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
16 Aug - 21 Aug
found 1 day ago
Return flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,623 reviews)
This was our second stay here. We were particularly impressed by the staff and customer service. It’s the kind we get in 5stars hotels overseas in the Middle East or SouthEast Asia. Impeccable. A special shout out to Pablo Criado for his warm and enthusiastic welcome and making sure that we had a great stay! I am now a fan and will only stay at Trump Chicago when in Chicago downtown.

Reviewed on 5 Jul 2025

The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
16 Aug - 21 Aug
found 1 day ago
Return flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (1,796 reviews)
Room was tiny for the price and no coffee maker in the room!

Reviewed on 5 Jul 2025

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
16 Aug - 21 Aug
found 1 day ago
Return flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,769 reviews)
Comfortable, stylish, friendly hotel in a fabulous location near Millennium Park, Art Institute, and Riverwalk. Friendly staff throughout but the cherry on top was Antoine who checked our bags and arranged out transportation to the airport when we checked out

Reviewed on 29 Jun 2025

The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
16 Aug - 21 Aug
found 1 day ago
Return flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,822 reviews)
Everyone is very helpful

Reviewed on 5 Jul 2025

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
6.6/10 (223 reviews)
"It was comfortable, I would stay again, but i do not like the $100 deposit plus paying for the room. The deposit was for in case I smoked in the room. They need to get rid of that."

Reviewed on 30 Jun 2025

Get rates
Motel Sun Inn
LA VILLA MOTEL
LA VILLA MOTEL
2 out of 5
1401 Sheridan Rd, Winthrop Harbor, IL
Fully refundable
The price is ₹5,235 per night from 14 Jul to 15 Jul
₹5,235
₹6,072 total
14 Jul - 15 Jul
includes taxes & fees
6.2/10 (34 reviews)
"Clean and quick"

Reviewed on 1 Jun 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 ₹9,726 per night from 13 Jul to 14 Jul
₹9,726
₹10,794 total
13 Jul - 14 Jul
includes taxes & fees
8.4/10 Very Good! (1,000 reviews)
"It was an awesome experience"

Reviewed on 30 Jun 2025

DoubleTree by Hilton Libertyville - Mundelein
See all 602 properties in Winthrop Harbor
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 ₹43,356 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.