Search Deals onSterling Vacation Packages
Sterling Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago
Save 100% on your flight
Price was $247, price is now $149 per person
$149
per person
Nov 25 - Nov 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4.5-star 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.
Trump International Hotel & Tower Chicago
Save 100% on your flight
Price was $739, price is now $410 per person
$410
per person
Jan 7 - Jan 10
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.
Hotel Riu Plaza Chicago
Save 100% on your flight
Price was $286, price is now $162 per person
$162
per person
Nov 25 - Nov 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Hotel Felix River North/Magnificent Mile
Save 100% on your flight
Price was $306, price is now $179 per person
$179
per person
Jan 7 - Jan 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star 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.
Park Hyatt Chicago
Save 100% on your flight
Price was $993, price is now $610 per person
$610
per person
Dec 26 - Dec 29
found 24 hours ago
Roundtrip flight included
Dallas (DFW) 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 in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Hilton Chicago O'Hare Airport
Save 100% on your flight
Price was $345, price is now $213 per person
$213
per person
Jan 9 - Jan 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Allstate Arena and The Dome at the Parkway Bank Sports Complex are located nearby.
Level Chicago - River North
Save 100% on your flight
Price was $732, price is now $458 per person
$458
per person
Dec 30 - Jan 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Level Chicago Fulton Market
Save 100% on your flight
Price was $639, price is now $409 per person
$409
per person
Dec 30 - Jan 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star hotel in Chicago. Enjoy free WiFi, an outdoor pool, and parking (surcharge). Popular attractions Chicago Riverwalk and Michigan Avenue 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.
Thu, Dec 11 - Mon, Dec 15
LAS
Harry Reid Intl.
RFD
Greater Rockford
$141 Roundtrip, found 1 day ago
$141
Roundtrip
found 1 day ago
Tue, Nov 18 - Sat, Dec 6
AUS
Austin-Bergstrom Intl.
MLI
Quad City Intl.
$194 Roundtrip, found 1 day ago
$194
Roundtrip
found 1 day ago
Tue, Oct 21 - Sun, Oct 26
ATL
Hartsfield-Jackson Atlanta Intl.
PIA
Greater Peoria Regional
$238 Roundtrip, found 2 days ago
$238
Roundtrip
found 2 days ago
Wed, Oct 29 - Sat, Nov 1
SEA
Seattle - Tacoma Intl.
PIA
Greater Peoria Regional
$282 Roundtrip, found 5 days ago
$282
Roundtrip
found 5 days ago
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