Search Deals onSteward Vacation Packages
Steward Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.

theWit Chicago, a Hilton Hotel
Save 100% on your flight
Price was $332, price is now $173 per person
$173
per person
Jan 9 - Jan 12
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.

Pendry Chicago
Save 100% on your flight
Price was $470, price is now $232 per person
$232
per person
Jan 9 - Jan 12
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.

Hilton Grand Vacations Club Chicago Magnificent Mile
Save 100% on your flight
Price was $366, price is now $193 per person
$193
per person
Jan 9 - Jan 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 3.5-star hotel in Chicago. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Level Chicago – Old Town
Save 100% on your flight
Price was $493, price is now $261 per person
$261
per person
Jan 9 - Jan 12
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.

Trump International Hotel & Tower Chicago
Price was $767, price is now $422 per person
$422
per person
Jan 9 - Jan 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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
Save 100% on your flight
Price was $370, price is now $214 per person
$214
per person
Jan 9 - Jan 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Grant Park and Millennium Park are located nearby.

Palmer House a Hilton Hotel
Save 100% on your flight
Price was $340, price is now $202 per person
$202
per person
Jan 9 - Jan 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star luxury 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 Chicago Riverwalk are located nearby.

The Royal Sonesta Chicago Downtown
Save 100% on your flight
Price was $307, price is now $183 per person
$183
per person
Jan 9 - Jan 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Steward Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.



Steward 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, Feb 14 - Tue, Feb 17
MCO
Orlando Intl.
RFD
Greater Rockford
$149 Roundtrip, found 5 hours ago
$149
Roundtrip
found 5 hours ago

Sat, Feb 14 - Tue, Feb 17
MCO
Orlando Intl.
RFD
Greater Rockford
$158 Roundtrip, found 5 hours ago
$158
Roundtrip
found 5 hours ago

Tue, Feb 17 - Thu, Feb 19
LAS
Harry Reid Intl.
RFD
Greater Rockford
$159 Roundtrip, found 2 days ago
$159
Roundtrip
found 2 days ago

Wed, Nov 26 - Sun, Nov 30
MSP
Minneapolis - St. Paul Intl.
RFD
Greater Rockford
$424 Roundtrip, found 5 days ago
$424
Roundtrip
found 5 days ago
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