Winthrop Harbor Vacations from $715
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, 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.
Hotel Riu Plaza Chicago
Downtown Chicago
$1,077
per person
Oct 27 - Nov 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (5,045 reviews)
Fantastic breakfast, great location, great room. The rooftop terrace was amazing, but we wishes we had known to make a reservation to be able to enjoy a drink there.
Reviewed on Aug 26, 2026
Don't see what you're looking for?
See all available trips from Columbus to Winthrop Harbor
View all tripsStay near popular Winthrop Harbor attractions
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
Explore the waterfront in Winthrop Harbor with a trip to North Point Marina. While you're in the area, stroll along the beaches.
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.
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.
Winthrop Harbor Hotel Deals
LA VILLA MOTEL
1401 Sheridan Rd Winthrop Harbor IL
Fully refundableReserve now, pay when you stay
$56 nightly
$65 total
Sep 1 - Sep 2
Total with taxes and fees
6.6/10 (80 reviews)
"Don't bother."
Reviewed on Aug 24, 2026
Motel Sun Inn
301 Sheridan Road Winthrop Harbor IL
Fully refundableReserve now, pay when you stay
$73 nightly
$85 total
Aug 30 - Aug 31
Total with taxes and fees
7/10 Good! (291 reviews)
"It was clean and staff was friendly"
Reviewed on Aug 24, 2026
La Quinta Inn & Suites by Wyndham Chicago Gurnee
5688 Northridge Rd Gurnee IL
Fully refundableReserve now, pay when you stay
$72 nightly
$81 total
Aug 31 - Sep 1
Total with taxes and fees
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
Frequently asked questions
How much does a Winthrop Harbor vacation package cost?
You'll find cheap prices from $715 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
- Beach Park Vacations
- The People's Choice Family Fun Center
- Depaul Art Museum
- Michigan Avenue
- Chicago City Hall
- Park West
- Illinois Centennial Memorial Column
- Wrigley Building
- Cadillac Palace Theatre
- Goodman Theater
- Chicago Place Mall
- Gurnee Vacations
- Holy Name Cathedral
- Holy Trinity Russian Orthodox Cathedral
- Graceland Cemetery
- Chicago Children's Museum
- Cyrus McCormick Mansion
- Genesee Theater
- St Nicholas Ukrainian Catholic Cathedral
- Asylum Skate Park
- Waukegan Harbor
- Cooking & Hospitality Institute of Chicago
- Naval Base Great Lakes
- International Museum of Surgical Science
- Northwestern Memorial Hospital
- Marshall Field Building
- Montrose Beach
- 360 CHICAGO
- Rosalind Franklin University of Medicine and Science
- Northalsted Vacations
- Saint Joseph Hospital
- Bonnie Brook Golf Course
- Henry Gerber House
- Skydeck Ledge
- Rookery
- Antioch Vacations
- College of Lake County
- Humboldt Park
- Farm-In-The-Zoo
- Depaul University-Lincoln Park
- Depaul University-Loop Campus
- Wrigley View Rooftop
- Apollo Theater Chicago
- Flat Iron Building
- Jack Benny Center for the Arts
- Shops at North Bridge
- Hutchinson Street Historic District
- Baha'i House of Worship
- North Chicago Vacations
- Picasso Statue
- Wicker Park Vacations
- Cancer Treatment Centers of America Midwestern Regional Medical Center
- Navy Pier
- Armitage Avenue
- Three Brothers Theatre
- Carbide and Carbon Building
- Wadsworth Vacations
- Illinois Beach State Park
- Gorilla Tango Theatre
- South Pond
- Waukegan BMX Track
- University of Illinois Chicago
- Vic Theatre
- Six Flags Great America
- Tribune Tower
- Briar Street Theatre
- Defiant Theatre
- Waukegan Vacations
- Gold Pyramid House
- The Salt Shed
- Gurnee Mills
- Lincoln Park
- Gold Coast Vacations
- Louis A. Weiss Memorial Hospital
- Merchandise Mart
- Legoland® Discovery Center
- Driehaus Museum
- 900 North Michigan Shops
- Magnificent Mile Vacations
- Our Lady of Lourdes Church
- Advocate Illinois Masonic Medical Center
- Marina City
- Monique Meloche Gallery
- St. Clements Church
- Lincoln Park Vacations
- St. Josaphat Church
- Second City
- Edgewater Vacations
- St. John Cantius Church
- Goose Island Vacations
- Lakeview Vacations
- Chicago Vacations
- Fourth Presbyterian Church
- Elks Veterans Memorial
- Riviera Theatre
- Lighthouse ArtSpace Chicago
- Annunciation Greek Orthodox Cathedral
- Zion Vacations
- Dave & Buster's
- Great Wolf Lodge Water Park
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
