Search Deals onWinfield Vacation Packages
Winfield Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
The Allegro Royal Sonesta Hotel Chicago Loop
per person
Jun 20 - Jun 23
found 1 day ago
Roundtrip flight included
New York (JFK) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and WiFi (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
The Chicago Hotel Collection River North
Save 100% on your flight
per person
May 16 - May 24
found 22 hours ago
Roundtrip non-stop flight included
New York (JFK) 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.
Swissotel - Chicago
Save 100% on your flight
per person
Jun 20 - Jun 23
found 1 day ago
Roundtrip flight included
New York (JFK) 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.
L7 Chicago by LOTTE
Save 100% on your flight
per person
Jun 20 - Jun 23
found 1 day ago
Roundtrip flight included
New York (JFK) to Chicago (ORD)
Book a stay at this boutique 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 Chicago Riverwalk and Michigan Avenue are located nearby.
Level Chicago – Old Town
Save 100% on your flight
per person
Jun 20 - Jun 23
found 1 day ago
Roundtrip flight included
New York (JFK) 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.
Fairmont Chicago at Millennium Park
per person
May 20 - May 22
found 1 day ago
Roundtrip flight included
New York (JFK) 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.
Best Motel By OYO Chicago I-90
per person
May 22 - May 29
found 1 day ago
Roundtrip non-stop flight included
St. Louis (STL) to Chicago (ORD)
Stay at this property in Chicago. Enjoy free parking, a 24-hour front desk, and daily housekeeping. Popular attractions Soldier Field and Chicago Museum of Science and Industry are located nearby.
Pendry Chicago
Save 100% on your flight
per person
Jun 20 - Jun 23
found 1 day ago
Roundtrip flight included
New York (JFK) 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.
Winfield Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Winfield 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 2 days ago
$124
Roundtrip
found 2 days ago
Tue, Apr 22 - Sat, Apr 26
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$189 Roundtrip, found 2 days ago
$189
Roundtrip
found 2 days ago
Tue, Apr 22 - Sat, Apr 26
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$189 Roundtrip, found 2 days ago
$189
Roundtrip
found 2 days ago
Sat, Apr 19 - Wed, Apr 23
LAX
Los Angeles Intl.
MDW
Midway Intl.
$253 Roundtrip, found 2 days ago
$253
Roundtrip
found 2 days ago
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