Search Deals onWinthrop Harbor Vacation Packages
Winthrop Harbor Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
The Chicago Hotel Collection River North
Save 100% on your flight
per person
May 8 - May 12
found 1 day ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
Stay at this 3-star hotel in Chicago. Enjoy free WiFi, a fitness center, and 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.
Pendry Chicago
Save 100% on your flight
per person
Jun 12 - Jun 15
found 1 day ago
Roundtrip flight included
Greenville (GSP) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
La Banque Hotel
Save 100% on your flight
per person
Jun 3 - Jun 6
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)
Stay at this 4-star golf hotel in Homewood. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff in our reviews. Popular attractions Ravisloe Country Club and Oak Hill Park are located nearby.
Fairmont Chicago at Millennium Park
per person
May 22 - May 25
found 1 day ago
Roundtrip flight included
Greenville (GSP) to Chicago (ORD)
Book a stay at this spa hotel in Chicago. Enjoy a full-service spa, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
The Glen Club
Save 100% on your flight
per person
May 8 - May 12
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)
Stay at this 3.5-star golf hotel in Glenview. Enjoy free WiFi, free parking, and a golf course. Our guests praise the helpful staff in our reviews. Popular attractions The Glen Club and Kohl Children's Museum are located nearby.
Palmer House a Hilton Hotel
per person
Jun 12 - Jun 15
found 1 day ago
Roundtrip flight included
Greenville (GSP) to Chicago (ORD)
Book a stay at this spa hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Art Institute of Chicago and Chicago Riverwalk are located nearby.
Level Chicago – Old Town
Save 100% on your flight
per person
Jun 12 - Jun 15
found 1 day ago
Roundtrip flight included
Greenville (GSP) to Chicago (ORD)
Stay at this 4-star spa aparthotel in Chicago. Enjoy free WiFi, an outdoor pool, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Winthrop Harbor Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Winthrop Harbor Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Wed, Apr 23 - Sat, Apr 26
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$124 Roundtrip, found 1 day ago
$124
Roundtrip
found 1 day ago
Tue, Apr 22 - Sat, Apr 26
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$189 Roundtrip, found 1 day ago
$189
Roundtrip
found 1 day ago
Tue, Apr 22 - Sat, Apr 26
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$189 Roundtrip, found 1 day ago
$189
Roundtrip
found 1 day ago
Wed, Jul 9 - Wed, Jul 9
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$251 Roundtrip, found 2 days ago
$251
Roundtrip
found 2 days ago
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