Search Deals on
Steward Vacation Packages

Build your package with 2 more options

Steward Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
The Emily Hotel

The Emily Hotel

4 out of 5
Save 100% on your flight
Price was $615, price is now $422 per person
$422
per person
Nov 23 - Nov 27
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, 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.

The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Save 100% on your flight
Price was $708, price is now $435 per person
$435
per person
Dec 10 - Dec 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury 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 Michigan Avenue and Chicago Riverwalk are located nearby.

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
Price was $1,196, price is now $737 per person
$737
per person
Nov 23 - Nov 27
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.
Amazing stay. Love the balcony view. Parking was easy and accessible. Will be back!

Reviewed on Sep 19, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $1,130, price is now $717 per person
$717
per person
Nov 11 - Nov 15
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.

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Save 100% on your flight
Price was $700, price is now $445 per person
$445
per person
Nov 23 - Nov 27
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.
Amazing place to stay in Chicago!

Reviewed on Sep 18, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
Price was $1,258, price is now $859 per person
$859
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this 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.
Place in the heart of the city. Accessable to all establishment. Staffs are great. Feels home

Reviewed on Sep 19, 2026

Holiday Inn Chicago North-Evanston by IHG

Holiday Inn Chicago North-Evanston by IHG

3 out of 5
Save 100% on your flight
Price was $1,152, price is now $792 per person
$792
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Evanston. Enjoy free WiFi, room service, and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Ryan Field and Baha'i House of Worship are located nearby.

Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

4.5 out of 5
Save 100% on your flight
Price was $731, price is now $508 per person
$508
per person
Nov 24 - Nov 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.

Steward Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $705, price is now $433 per person
$433
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $708, price is now $435 per person
$435
per person
Dec 10 - Dec 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,196, price is now $737 per person
$737
per person
Nov 23 - Nov 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,130, price is now $717 per person
$717
per person
Nov 11 - Nov 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

Steward Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $824, price is now $505 per person
$505
per person
Nov 26 - Dec 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,967, price is now $1,092 per person
$1,092
per person
Nov 28 - Dec 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,571, price is now $919 per person
$919
per person
Nov 28 - Dec 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,298, price is now $774 per person
$774
per person
Nov 28 - Dec 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

American Airlines
Sat, Sep 26 - Tue, Sep 29
PHX
Sky Harbor Intl.
RFD
Greater Rockford
$486 Roundtrip, found 2 hours ago
$486
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Sat, Sep 26 from Sky Harbor Intl. to Greater Rockford, returning Tue, Sep 29, priced at $486 found 2 hours ago
American Airlines
Sat, Sep 26 - Tue, Sep 29
PHX
Sky Harbor Intl.
RFD
Greater Rockford
$496 Roundtrip, found 13 hours ago
$496
Roundtrip
found 13 hours ago
Select American Airlines flight, departing Sat, Sep 26 from Sky Harbor Intl. to Greater Rockford, returning Tue, Sep 29, priced at $496 found 13 hours ago
American Airlines
Sat, Sep 26 - Tue, Sep 29
PHX
Sky Harbor Intl.
RFD
Greater Rockford
$526 Roundtrip, found 14 hours ago
$526
Roundtrip
found 14 hours ago
Select American Airlines flight, departing Sat, Sep 26 from Sky Harbor Intl. to Greater Rockford, returning Tue, Sep 29, priced at $526 found 14 hours ago
American Airlines
Sat, Sep 26 - Tue, Sep 29
PHX
Sky Harbor Intl.
RFD
Greater Rockford
$526 Roundtrip, found 4 days ago
$526
Roundtrip
found 4 days ago
Select American Airlines flight, departing Sat, Sep 26 from Sky Harbor Intl. to Greater Rockford, returning Tue, Sep 29, priced at $526 found 4 days ago