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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
Price was $679, price is now $437 per person
$437
per person
Jun 11 - Jun 14
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

Hotel Riu Plaza Chicago

4 out of 5
Price was $1,007, price is now $522 per person
$522
per person
Jun 11 - Jun 14
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 $2,321, price is now $1,418 per person
$1,418
per person
Jun 4 - Jun 8
found 18 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and parking (surcharge). Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Save 100% on your flight
Price was $1,296, price is now $813 per person
$813
per person
Jun 4 - Jun 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.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
Price was $1,322, price is now $836 per person
$836
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Save 100% on your flight
Price was $835, price is now $550 per person
$550
per person
Jun 13 - Jun 16
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 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.
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Price was $760, price is now $503 per person
$503
per person
Jun 11 - Jun 14
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.
Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

3 out of 5
Save 100% on your flight
Price was $1,418, price is now $942 per person
$942
per person
Jun 4 - Jun 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, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Grant Park and Soldier Field are located nearby.

Sterling Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was $1,007, price is now $522 per person
$522
per person
Jun 11 - Jun 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,714, price is now $1,038 per person
$1,038
per person
Jun 4 - Jun 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $2,321, price is now $1,418 per person
$1,418
per person
Jun 4 - Jun 8
found 18 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,296, price is now $813 per person
$813
per person
Jun 4 - Jun 8
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.
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,470, price is now $913 per person
$913
per person
Jun 1 - Jun 6
found 1 hour ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was $1,900, price is now $998 per person
$998
per person
Jun 1 - Jun 6
found 1 hour ago
Roundtrip flight included
Dallas (DFW) 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 $1,667, price is now $996 per person
$996
per person
Jun 1 - Jun 6
found 1 hour ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,397, price is now $943 per person
$943
per person
Jun 1 - Jun 6
found 1 hour ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)

Top Flight Deals

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

American Airlines
Mon, Apr 27 - Fri, May 1
ATL
Hartsfield-Jackson Atlanta Intl.
RFD
Greater Rockford
$228 Roundtrip, found 2 hours ago
$228
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Mon, Apr 27 from Hartsfield-Jackson Atlanta Intl. to Greater Rockford, returning Fri, May 1, priced at $228 found 2 hours ago
United
Tue, Jun 2 - Tue, Jun 9
IAH
George Bush Intercontinental
MLI
Quad City Intl.
$243 Roundtrip, found 6 days ago
$243
Roundtrip
found 6 days ago
Select United flight, departing Tue, Jun 2 from George Bush Intercontinental to Quad City Intl., returning Tue, Jun 9, priced at $243 found 6 days ago
American Airlines
Thu, Apr 9 - Mon, Apr 13
BOS
Logan Intl.
RFD
Greater Rockford
$262 Roundtrip, found 1 day ago
$262
Roundtrip
found 1 day ago
Select American Airlines flight, departing Thu, Apr 9 from Logan Intl. to Greater Rockford, returning Mon, Apr 13, priced at $262 found 1 day ago
Bargain Flight
Tue, Mar 31 - Wed, Apr 8
ATL
Hartsfield-Jackson Atlanta Intl.
PIA
Greater Peoria Regional
$265 Roundtrip, found 8 hours ago
$265
Roundtrip
found 8 hours ago
Select Bargain Flight flight, departing Tue, Mar 31 from Hartsfield-Jackson Atlanta Intl. to Greater Peoria Regional, returning Wed, Apr 8, priced at $265 found 8 hours ago