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Sterling Vacation Packages

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Sterling Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Save 100% on your flight
Price was $817, price is now $568 per person
$568
per person
Aug 4 - Aug 8
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.
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Save 100% on your flight
Price was $1,121, price is now $688 per person
$688
per person
Aug 4 - Aug 8
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.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $1,167, price is now $726 per person
$726
per person
Aug 4 - Aug 8
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

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Save 100% on your flight
Price was $1,147, price is now $769 per person
$769
per person
Aug 4 - Aug 8
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.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
Price was $1,271, price is now $860 per person
$860
per person
Jul 9 - Jul 12
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.
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Save 100% on your flight
Price was $1,295, price is now $887 per person
$887
per person
Aug 4 - Aug 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 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Urban Chicago Oasis

Urban Chicago Oasis

2 out of 5
Save 100% on your flight
Price was $1,272, price is now $876 per person
$876
per person
Jul 11 - Jul 14
found 22 hours ago
Roundtrip flight included
Minneapolis (MSP) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, laundry facilities, and balconies or patios. Popular attractions Wrigley Field and Michigan Avenue are located nearby.
Hotel 55 Chicago Downtown

Hotel 55 Chicago Downtown

4 out of 5
Save 100% on your flight
Price was $908, price is now $633 per person
$633
per person
Jul 15 - Jul 18
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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 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.
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,121, price is now $688 per person
$688
per person
Aug 4 - Aug 8
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 $1,167, price is now $726 per person
$726
per person
Aug 4 - Aug 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
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 $1,147, price is now $769 per person
$769
per person
Aug 4 - Aug 8
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 $1,271, price is now $860 per person
$860
per person
Jul 9 - Jul 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

Sterling Vacation Packages 5-7 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 $1,310, price is now $755 per person
$755
per person
Aug 10 - Aug 15
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 $1,299, price is now $773 per person
$773
per person
Aug 10 - Aug 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
JW Marriott Chicago

JW Marriott Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,399, price is now $848 per person
$848
per person
Jul 6 - Jul 11
found 22 hours ago
Roundtrip flight included
Minneapolis (MSP) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,410, price is now $903 per person
$903
per person
Jul 6 - Jul 11
found 22 hours ago
Roundtrip flight included
Minneapolis (MSP) 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, Jul 4 - Sat, Jul 4
AUS
Austin-Bergstrom Intl.
MLI
Quad City Intl.
$230 Roundtrip, found 2 days ago
$230
Roundtrip
found 2 days ago
Select American Airlines flight, departing Sat, Jul 4 from Austin-Bergstrom Intl. to Quad City Intl., returning Sat, Jul 4, priced at $230 found 2 days ago
American Airlines
Fri, Sep 4 - Sat, Sep 5
AUS
Austin-Bergstrom Intl.
RFD
Greater Rockford
$285 Roundtrip, found 4 days ago
$285
Roundtrip
found 4 days ago
Select American Airlines flight, departing Fri, Sep 4 from Austin-Bergstrom Intl. to Greater Rockford, returning Sat, Sep 5, priced at $285 found 4 days ago
Delta
Sat, Jun 27 - Mon, Jun 29
DEN
Denver Intl.
MLI
Quad City Intl.
$289 Roundtrip, found 4 days ago
$289
Roundtrip
found 4 days ago
Select Delta flight, departing Sat, Jun 27 from Denver Intl. to Quad City Intl., returning Mon, Jun 29, priced at $289 found 4 days ago
American Airlines
Sat, Jun 20 - Tue, Jun 23
ATL
Hartsfield-Jackson Atlanta Intl.
RFD
Greater Rockford
$290 Roundtrip, found 1 day ago
$290
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, Jun 20 from Hartsfield-Jackson Atlanta Intl. to Greater Rockford, returning Tue, Jun 23, priced at $290 found 1 day ago