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

The Blackstone, Autograph Collection
Save 100% on your flight  
Price was $705, price is now $370 per person
$370
per person
Jan 16 - Jan 23
found 20 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy a 24-hour fitness center, parking (surcharge), and onsite spa services. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Grant Park and Millennium Park are located nearby. 

The Westin Michigan Avenue Chicago
Price was $3,682, price is now $1,112 per person
$1,112
per person
Jan 16 - Jan 23
found 1 hour ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy a full-service spa, 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. 

Pendry Chicago
Price was $1,015, price is now $479 per person
$479
per person
Jan 16 - Jan 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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. 

Hotel Riu Plaza Chicago
Save 100% on your flight  
Price was $751, price is now $372 per person
$372
per person
Jan 16 - Jan 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby. 

theWit Chicago, a Hilton Hotel
Save 100% on your flight  
Price was $731, price is now $372 per person
$372
per person
Jan 16 - Jan 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4.5-star luxury 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 Chicago Riverwalk and Millennium Park are located nearby. 

The Emily Hotel
Price was $1,071, price is now $546 per person
$546
per person
Jan 16 - Jan 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star business-friendly 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 United Center and Chicago Riverwalk are located nearby. 

Level Chicago – Old Town
Price was $1,110, price is now $570 per person
$570
per person
Jan 16 - Jan 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star family-friendly aparthotel in Chicago. Enjoy free WiFi, an outdoor pool, and a rooftop terrace. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby. 

Level Chicago - River North
Save 100% on your flight  
Price was $970, price is now $535 per person
$535
per person
Jan 16 - Jan 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a fitness center. 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.

Thu, Nov 27 - Tue, Dec 2
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$102 Roundtrip, found 1 day ago
$102
Roundtrip
found 1 day ago

Fri, Nov 14 - Wed, Nov 19
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$120 Roundtrip, found 9 hours ago
$120
Roundtrip
found 9 hours ago

Thu, Nov 27 - Tue, Dec 2
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$182 Roundtrip, found 1 day ago
$182
Roundtrip
found 1 day ago

Thu, Dec 4 - Mon, Dec 15
FCO
Fiumicino - Leonardo da Vinci Intl.
ORD
O'Hare Intl.
$572 Roundtrip, found 4 days ago
$572
Roundtrip
found 4 days ago
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