Winthrop Harbor Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Winthrop Harbor Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
The Whitehall Hotel, BW Premier Collection
Downtown Chicago
$541
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Hotel Riu Plaza Chicago
Downtown Chicago
$932
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
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
Hotel Saint Clair- Magnificent Mile
Downtown Chicago
$603
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Swissotel - Chicago
Downtown Chicago
$905
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Pros: Location is excellent. View was excellent. They upgraded my room from the 4th floor to the 28th floor at no extra cost. Cleaned when I requested.
Cons: Staff was a bit snooty snooty hoity toity. Didn't know I had to pay for parking so that cost more than I budgeted for, it was also an unnecessary hassle to do due to poor internet connection. Confusing amenity fees that I thought I was properly taking advantage of but toward the end felt was taking advantage of me to extract more money. I requested some items be brought up to our room only for staff to tell me I had to come down to the lobby myself to grab them.
Ultimately I can summarize the experience easily as its not worth what I paid for. Also no pool but thats more on me for not checking for that ahead of time.
Reviewed on Aug 26, 2026
The Talbott, Autograph Collection
Downtown Chicago
$759
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
$636
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this boutique hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour health club, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
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See all available trips from Columbus to Winthrop Harbor
View all tripsWinthrop Harbor Vacation Packages
Trying to figure out a way to package your flight and hotel, while saving some money? The AARP Travel Center Powered by Expedia® can help you get everything you need, while saving you both money and some time. We're here to book everything you'll need to make your Winthrop Harbor trip one to remember. Our Travel Center is a one-stop shop where you can put together the best vacation package for you. We have an incredible choice of accommodations and flight, as well as Winthrop Harbor endeavors to pick from.
Winthrop Harbor Hotels
Our listings include lodgings that are close to all the Winthrop Harbor points of interest, and some that are just outside the city center for a more restful retreat.
From Winthrop Harbor hotels with pools and on-site restaurants, to boutique accommodations that add all the extra amenities, you'll get a hotel here that will make your trip amazing. With AARP Travel Center's Winthrop Harbor hotel packages, you not only get a great rate on your flight, but also a terrific place to stay.
Things to do in Winthrop Harbor
Winthrop Harbor is the perfect town when you wish to get away from it all. With only around 6,818 people in the city, this cozy town is just right for a quite vacation. With the city's thriving artistic community and plenty of interest for history buffs you may have a hard time fitting everything into one trip.
The AARP Travel Center "Things to Do" page has more great activities that you can book.
Book Together and Save
As an AARP Member, you get to cash in on all the great deals. You'll save on select hotels worldwide, flights, and also car rentals. No matter what Winthrop Harbor vacation bundle you select, you can rest easy knowing that you already saved on your trip. So what are you waiting for? Book today and get ready for your Winthrop Harbor vacation.
Top Hotel Deals
LA VILLA MOTEL
1401 Sheridan Rd Winthrop Harbor IL
Stay at this motel in Winthrop Harbor. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Illinois Beach State Park and Elizabeth Park ...
Motel Sun Inn
301 Sheridan Road Winthrop Harbor IL
Stay at this motel in Winthrop Harbor. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Illinois Beach State Park and Spring Bluff ...
La Quinta Inn & Suites by Wyndham Chicago Gurnee
5688 Northridge Rd Gurnee IL
Book a stay at this business-friendly hotel in Gurnee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Great Wolf Lodge Illinois
1700 Nations Dr Gurnee IL
Book a stay at this family-friendly resort in Gurnee. Enjoy 6 indoor pools, 5 restaurants, and 2 bars/lounges. Our guests praise the helpful staff in our reviews. ...
Sonesta ES Suites Chicago Waukegan Gurnee
1440 S White Oak Dr Waukegan IL
Book a stay at this business-friendly hotel in Waukegan. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Hotel Indigo Chicago-Vernon Hills by IHG
450 N Milwaukee Ave Vernon Hills IL
Book a stay at this boutique hotel in Vernon Hills. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff in our reviews. Popular ...
DoubleTree by Hilton Libertyville - Mundelein
510 E IL Route 83 Mundelein IL
Book a stay at this business-friendly hotel in Mundelein. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
Days Inn by Wyndham Waukegan
630 N Green Bay Road Waukegan IL
Stay at this motel in Waukegan. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Six Flags Great America and Gurnee Mills are located ...
The Inn on Sheridan
2723 Sheridan Rd Zion IL
Book a stay at this business-friendly hotel in Zion. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...
Best Western Executive Inn Kenosha/Pleasant Prairie
7220 122nd Ave Kenosha WI
Book a stay at this business-friendly hotel in Kenosha. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
Hampton Inn Chicago - Gurnee
5550 Grand Ave Gurnee IL
Book a stay at this business-friendly hotel in Gurnee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Days Inn by Wyndham Great Lakes Naval Base
3000 North Skokie Highway North Chicago IL
Book a stay at this business-friendly hotel in North Chicago. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
Americas Best Value Inn & Suites Racine
5419 Durand Ave Mount Pleasant WI
Book a stay at this business-friendly hotel in Mount Pleasant. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the helpful staff in ...
Illinois Beach Hotel
100 Lake Front Dr Zion IL
Stay at this hotel in Zion. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions ...
Wyndham Garden Kenosha Harborside
5125 6th Ave Kenosha WI
Book a stay at this business-friendly hotel in Kenosha. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the breakfast and the helpful ...
Don't see what you're looking for?
See all available properties in Winthrop Harbor
View all propertiesLowest 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.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Sat, Oct 17 - Sat, Oct 24
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$148
Roundtrip
found 6 hours ago
Thu, Oct 15 - Mon, Oct 19
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$173
Roundtrip
found 4 days ago
Thu, Oct 15 - Mon, Oct 19
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$183
Roundtrip
found 4 days ago
Thu, Oct 1 - Sun, Oct 4
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$197
Roundtrip
found 3 days ago
Sat, Oct 17 - Sat, Oct 24
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$377
Roundtrip
found 6 hours ago
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