Search Deals onWinthrop Harbor Vacation Packages
Winthrop Harbor Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.

Palmer House a Hilton Hotel
per person
Aug 17 - Aug 19
found 2 hours ago
Roundtrip flight included
Austin (AUS) 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 Millennium Park and Art Institute of Chicago are located nearby.

Swissotel - Chicago
Save 100% on your flight
per person
Jul 17 - Jul 19
found 1 day ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Book a stay at this eco-certified 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.

The Chicago Hotel Collection - Wrigleyville
Save 100% on your flight
per person
Aug 17 - Aug 19
found 1 hour ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Stay at this 3.5-star hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and room service. Our guests praise the clean rooms in our reviews. Popular attractions Wrigley Field and Michigan Avenue are located nearby.

Trump International Hotel & Tower Chicago
Save 100% on your flight
per person
Jul 17 - Jul 19
found 1 day ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.

Hilton Chicago/Magnificent Mile Suites
per person
Jul 17 - Jul 19
found 1 day ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. 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
per person
Jul 17 - Jul 19
found 1 day ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Stay at this 4-star 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.

InterContinental Chicago Magnificent Mile by IHG
per person
Jul 17 - Jul 19
found 1 day ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the pool and 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.

Tue, Jul 22 - Tue, Jul 29
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$140 Roundtrip, found 16 hours ago
$140
Roundtrip
found 16 hours ago

Tue, Aug 26 - Tue, Sep 2
FCO
Fiumicino - Leonardo da Vinci Intl.
ORD
O'Hare Intl.
$583 Roundtrip, found 4 hours ago
$583
Roundtrip
found 4 hours ago

Thu, Jun 19 - Mon, Aug 4
HKG
Hong Kong Intl.
ORD
O'Hare Intl.
$966 Roundtrip, found 20 hours ago
$966
Roundtrip
found 20 hours ago

Tue, Nov 11 - Thu, Nov 27
PVG
Pudong Intl.
ORD
O'Hare Intl.
$990 Roundtrip, found 4 hours ago
$990
Roundtrip
found 4 hours ago
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