Search Deals onSteward Vacation Packages
Steward Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Save 100% on your flight
Price was $653, price is now $408 per person
$408
per person
Dec 18 - Dec 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
Swissotel - Chicago
Save 100% on your flight
Price was $738, price is now $459 per person
$459
per person
Dec 18 - Dec 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
The hotel is very centrally located! We got a room with a view and so worth it. Get the lake view you won’t be disappointed! Will definitely stay there again!
Reviewed on Oct 11, 2026
Level Chicago – Old Town
Save 100% on your flight
Price was $1,568, price is now $976 per person
$976
per person
Dec 20 - Dec 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this 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.
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
Save 100% on your flight
Price was $672, price is now $424 per person
$424
per person
Dec 11 - Dec 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
Level Chicago Fulton Market
Save 100% on your flight
Price was $798, price is now $522 per person
$522
per person
Dec 25 - Dec 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a fitness center. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
The hotel was really nice. Wish that parking was included.
Reviewed on Oct 6, 2026
Pendry Chicago
Save 100% on your flight
Price was $659, price is now $434 per person
$434
per person
Dec 17 - Dec 20
found 19 hours ago
Roundtrip flight included
Atlanta (ATL) 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.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Save 100% on your flight
Price was $784, price is now $531 per person
$531
per person
Dec 18 - Dec 22
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, 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.
Villa Christina
Save 100% on your flight
Price was $677, price is now $460 per person
$460
per person
Dec 8 - Dec 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this guesthouse in Chicago. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Wintrust Arena and Obama Presidential Center are located nearby.
Property was maintained very well, very clean with some artful style. Staff reaponsed quickly fie any needs or inquiry. Feels like a home. Community is safe and neighbors are nice. Street parking is reletively easy.
Reviewed on Aug 4, 2026
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.
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