Search Deals onWinthrop Harbor Vacation Packages
Winthrop Harbor Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Le Méridien Essex Chicago
Save 100% on your flight
Price was $976, price is now $685 per person
$685
per person
Aug 12 - Aug 16
found 13 hours ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Grant Park and Soldier Field are located nearby.
Swissotel - Chicago
Save 100% on your flight
Price was $2,288, price is now $1,400 per person
$1,400
per person
Jul 31 - Aug 3
found 13 hours ago
Roundtrip flight included
Mesa (AZA) 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.
Hotel Riu Plaza Chicago
Save 100% on your flight
Price was $1,740, price is now $1,114 per person
$1,114
per person
Jul 31 - Aug 3
found 13 hours ago
Roundtrip flight included
Mesa (AZA) 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.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Save 100% on your flight
Price was $1,998, price is now $1,331 per person
$1,331
per person
Jul 31 - Aug 3
found 13 hours ago
Roundtrip flight included
Mesa (AZA) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Navy Pier and Michigan Avenue are located nearby.
Viceroy Chicago
Save 100% on your flight
Price was $2,227, price is now $1,520 per person
$1,520
per person
Jul 29 - Aug 3
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a rooftop terrace. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Pendry Chicago
Save 100% on your flight
Price was $1,064, price is now $727 per person
$727
per person
Jul 8 - Jul 11
found 17 hours ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Kimpton Gray Hotel by IHG
Save 100% on your flight
Price was $2,167, price is now $1,483 per person
$1,483
per person
Jul 29 - Aug 3
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and WiFi (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
Spark by Hilton Matteson Chicago I 57
Save 100% on your flight
Price was $1,283, price is now $899 per person
$899
per person
Jul 14 - Jul 19
found 1 day ago
Roundtrip flight included
New York (NYC) to Chicago (ORD)
Book a stay at this business-friendly hotel in Matteson. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Credit Union 1 Amphitheatre and Odyssey Fun World 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.
Sat, Jul 4 - Wed, Jul 8
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$158 Roundtrip, found 1 day ago
$158
Roundtrip
found 1 day ago
Wed, Jul 8 - Thu, Jul 16
FCO
Fiumicino - Leonardo da Vinci Intl.
ORD
O'Hare Intl.
$874 Roundtrip, found 12 hours ago
$874
Roundtrip
found 12 hours ago
Mon, Jun 1 - Sun, Sep 6
PVG
Pudong Intl.
ORD
O'Hare Intl.
$1,183 Roundtrip, found 6 days ago
$1,183
Roundtrip
found 6 days ago
Tue, Jun 2 - Mon, Sep 7
SHA
Hongqiao Intl.
ORD
O'Hare Intl.
$1,568 Roundtrip, found 2 days ago
$1,568
Roundtrip
found 2 days ago
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