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

Hotel Felix River North/Magnificent Mile
Save 100% on your flight
Price was $1,200, price is now $717 per person
$717
per person
Aug 22 - Aug 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this boutique hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour health club, and valet 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.

Hotel Riu Plaza Chicago
Save 100% on your flight
Price was $1,673, price is now $927 per person
$927
per person
Aug 22 - Aug 28
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.

Sable at Navy Pier Chicago, Curio Collection by Hilton
Save 100% on your flight
Price was $2,105, price is now $1,280 per person
$1,280
per person
Aug 22 - Aug 28
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.

Fairmont Chicago at Millennium Park
Save 100% on your flight
Price was $1,162, price is now $750 per person
$750
per person
Sep 3 - Sep 8
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 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.

Eurostars Magnificent Mile
Save 100% on your flight
Price was $1,261, price is now $828 per person
$828
per person
Aug 22 - Aug 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this spa hotel in Chicago. Enjoy free WiFi, a full-service spa, and a 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.

LondonHouse Chicago, Curio Collection by Hilton
Save 100% on your flight
Price was $1,598, price is now $1,058 per person
$1,058
per person
Aug 22 - Aug 28
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 2 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.

The Talbott, Autograph Collection
Save 100% on your flight
Price was $1,215, price is now $814 per person
$814
per person
Sep 3 - Sep 8
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
Save 100% on your flight
Price was $1,365, price is now $925 per person
$925
per person
Aug 6 - Aug 9
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.
Sterling Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.



Sterling 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, Aug 19 - Tue, Sep 8
AUS
Austin-Bergstrom Intl.
MLI
Quad City Intl.
$236 Roundtrip, found 6 hours ago
$236
Roundtrip
found 6 hours ago

Thu, Aug 6 - Tue, Aug 11
AUS
Austin-Bergstrom Intl.
PIA
Greater Peoria Regional
$264 Roundtrip, found 9 hours ago
$264
Roundtrip
found 9 hours ago

Fri, Jul 24 - Fri, Jul 31
ATL
Hartsfield-Jackson Atlanta Intl.
RFD
Greater Rockford
$296 Roundtrip, found 6 hours ago
$296
Roundtrip
found 6 hours ago

Tue, Jul 28 - Tue, Aug 4
LAS
Harry Reid Intl.
MLI
Quad City Intl.
$302 Roundtrip, found 12 hours ago
$302
Roundtrip
found 12 hours ago
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