Winthrop Harbor Vacations from $263

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $1,045 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

The Latest Winthrop Harbor vacation packages

Price found within the past 48 hours. Click for updated prices.
Bridgeview Inn Chicago Area

Bridgeview Inn Chicago Area

2 out of 5
Save 100% on your flight
Price was $430, price is now $263 per person
$263
per person
Mar 16 - Mar 21
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
6.4/10 (105 reviews)
Newly remodeled room.

Reviewed on Oct 11, 2025

La Banque Hotel

La Banque Hotel

4 out of 5
Save 100% on your flight
Price was $628, price is now $354 per person
$354
per person
Apr 3 - Apr 6
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
9.4/10 Exceptional! (447 reviews)
The room was spotless and the staff was good. Loved the hotel. Was just an overnight stay. Wish we had stayed another day. Loved the area.

Reviewed on Nov 30, 2025

Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $947, price is now $588 per person
$588
per person
Mar 18 - Mar 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (317 reviews)
Room was very spacious and clean. The location was perfect walking distance from a lot great eating and tourists spots.

Reviewed on Dec 18, 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $860, price is now $538 per person
$538
per person
Apr 2 - Apr 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Staff was friendly did amazing job with checking us in

Reviewed on Dec 25, 2025

Waldorf Astoria Chicago

Waldorf Astoria Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,689, price is now $1,069 per person
$1,069
per person
Mar 22 - Mar 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
When we arrived at check in time, we were informed that our room was not ready but that we could upgrade at a discounted additional cost to a suite. At first, we didn't want to do that and decided to wait. The host provided complimentary round of drinks and meal for the wait. We decided to upgrade and I'm so glad that we did. The room was incredible and the service, from concierge, staff and valets, here is top notch. We ordered the Waldorf salad and Waldorf chocolate chip cookies because you have to if you stay here. Loved this place and will definitely return.

Reviewed on Jan 5, 2026

Don't see what you're looking for?
See all available trips from Columbus to Winthrop Harbor
View all trips

Winthrop Harbor Hotel Deals

Motel Sun Inn

Motel Sun Inn

2.5 out of 5
301 Sheridan Road Winthrop Harbor IL
Fully refundableReserve now, pay when you stay
$67 nightly
The price is $78 total per night from Jan 11 to Jan 12
$78 total
Jan 11 - Jan 12
Total with taxes and fees
6.8/10 (276 reviews)
I have stayed here several times in the last year and a half. The room is very clean! Staff is very kind and helpful! Good rate! Thank you again for everything!

Reviewed on Nov 11, 2025

Motel Sun Inn
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
Fully refundableReserve now, pay when you stay
$59 nightly
The price is $66 total per night from Feb 1 to Feb 2
$66 total
Feb 1 - Feb 2
Total with taxes and fees
7.8/10 Good! (1,477 reviews)
We had a great stay! The breakfast was delicious and fresh. Facilities were brand new and nice. Pool was nice and warm! There was some issue with the staff being rude and not kind, but otherwise it was great!

Reviewed on Jan 5, 2026

La Quinta Inn & Suites by Wyndham Chicago Gurnee
Wingate by Wyndham Gurnee

Wingate by Wyndham Gurnee

2.5 out of 5
6090 Gurnee Mills Blvd E Gurnee IL
Fully refundableReserve now, pay when you stay
$81 nightly
The price is $90 total per night from Jan 11 to Jan 12
$90 total
Jan 11 - Jan 12
Total with taxes and fees
8.8/10 Excellent! (1,000 reviews)
Fine

Reviewed on Jan 2, 2026

Wingate by Wyndham Gurnee
See all 675 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.

Find the Best Winthrop Harbor Vacation Packages

Winthrop Harbor Essential Information

Language
English
Currency
U.S dollars
Population
6,800
Max Temp Winter
30ºF
Max Temp Summer
75ºF

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Winthrop Harbor vacation package cost?
You'll find cheap prices from $263 on Expedia for your Winthrop Harbor getaway. However, factors like the hotel choice, length of stay and season will determine how much your vacation to Winthrop Harbor costs.
What are the cheapest months to go to Winthrop Harbor?
If you're hoping to book a cheap Winthrop Harbor vacation package, consider planning a trip in December, January and February. You'll usually find better prices on accommodations and flights during these months — perfect for budget-conscious travelers.
How many days is enough for Winthrop Harbor?
With a well-organized schedule, you can easily tick off the top Winthrop Harbor sights in a few days. But if you want to discover hidden gems or take day trips, think about booking your Winthrop Harbor vacation for longer.
How to find the best Winthrop Harbor package deals?
Landing a cheap Winthrop Harbor 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 Harbor 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 Harbor vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to arranging flights and accommodations individually. Better still, you can customize your Winthrop Harbor 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 vacation package to Winthrop Harbor?
If you're planning an impromptu Winthrop Harbor 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.
Does Expedia offer Book Now, Pay Later Winthrop Harbor vacation packages?
Jet off on your perfect escape to Winthrop Harbor with Expedia's Book Now, Pay Later vacations. There's no need to save up or wait until payday — we've partnered with online lender Affirm to give you more financial flexibility. Our vacation packages with payment plans allow you to spread the cost across 3, 6 or 12 months. With no hidden or late payment fees, it's a breeze to stick to your budget and snap up bargains before they disappear.

Explore a world of travel with Expedia

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