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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 $719, price is now $470 per person
$470
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
Save 100% on your flight
Price was $985, price is now $525 per person
$525
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.
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
Save 100% on your flight
Price was $796, price is now $497 per person
$497
per person
May 21 - May 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this 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.
Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

4.5 out of 5
Save 100% on your flight
Price was $1,591, price is now $1,008 per person
$1,008
per person
Jun 11 - Jun 16
found 4 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, 2 bars/lounges, and room service. Our guests praise the helpful staff and the clean rooms 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 $1,036, price is now $679 per person
$679
per person
Jun 11 - Jun 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 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.
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Save 100% on your flight
Price was $1,009, price is now $669 per person
$669
per person
May 21 - May 25
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.
Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4 out of 5
Save 100% on your flight
Price was $822, price is now $553 per person
$553
per person
Jun 26 - Jun 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 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.
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Save 100% on your flight
Price was $746, price is now $506 per person
$506
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.

Sterling Vacation Packages 3-4 Night Stays

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
Downtown Chicago
Save 100% on your flight
Price was $719, price is now $470 per person
$470
per person
Jun 11 - Jun 14
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 $985, price is now $525 per person
$525
per person
Jun 11 - Jun 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare
Save 100% on your flight
Price was $796, price is now $497 per person
$497
per person
May 21 - May 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,036, price is now $679 per person
$679
per person
Jun 11 - Jun 14
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.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,323, price is now $726 per person
$726
per person
Jun 11 - Jun 16
found 4 hours 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 $1,429, price is now $739 per person
$739
per person
Jun 14 - Jun 19
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 $1,726, price is now $1,017 per person
$1,017
per person
Jun 14 - Jun 19
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 $1,394, price is now $845 per person
$845
per person
Jun 11 - Jun 16
found 4 hours 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
Thu, Apr 9 - Mon, Apr 13
BOS
Logan Intl.
RFD
Greater Rockford
$238 Roundtrip, found 2 days ago
$238
Roundtrip
found 2 days ago
Select American Airlines flight, departing Thu, Apr 9 from Logan Intl. to Greater Rockford, returning Mon, Apr 13, priced at $238 found 2 days ago
American Airlines
Tue, Jun 2 - Tue, Jun 9
IAH
George Bush Intercontinental
MLI
Quad City Intl.
$243 Roundtrip, found 3 hours ago
$243
Roundtrip
found 3 hours ago
Select American Airlines flight, departing Tue, Jun 2 from George Bush Intercontinental to Quad City Intl., returning Tue, Jun 9, priced at $243 found 3 hours ago
American Airlines
Fri, May 29 - Sat, Aug 1
IAH
George Bush Intercontinental
RFD
Greater Rockford
$277 Roundtrip, found 2 hours ago
$277
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Fri, May 29 from George Bush Intercontinental to Greater Rockford, returning Sat, Aug 1, priced at $277 found 2 hours ago
United
Fri, May 29 - Sat, Aug 1
IAH
George Bush Intercontinental
PIA
Greater Peoria Regional
$292 Roundtrip, found 2 hours ago
$292
Roundtrip
found 2 hours ago
Select United flight, departing Fri, May 29 from George Bush Intercontinental to Greater Peoria Regional, returning Sat, Aug 1, priced at $292 found 2 hours ago