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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 $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.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
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.
Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Save 100% on your flight
Price was $993, price is now $610 per person
$610
per person
Dec 26 - Dec 29
found 21 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

Hilton Chicago O'Hare Airport

4 out of 5
Save 100% on your flight
Price was $345, price is now $213 per person
$213
per person
Jan 9 - Jan 11
found 24 hours 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

Level Chicago - River North

4 out of 5
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

Level Chicago Fulton Market

4 out of 5
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.
Waldorf Astoria Chicago

Waldorf Astoria Chicago

5 out of 5
Save 100% on your flight
Price was $838, price is now $537 per person
$537
per person
Dec 24 - Dec 26
found 1 day 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.
Viceroy Chicago

Viceroy Chicago

4.5 out of 5
Save 100% on your flight
Price was $998, price is now $655 per person
$655
per person
Dec 23 - Dec 28
found 1 hour ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a rooftop terrace. Our guests praise the bar and 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.
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 $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)
The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago

4.5 out of 5
Downtown Chicago
Price was $1,390, price is now $643 per person
$643
per person
Dec 22 - Dec 26
found 10 hours ago
Roundtrip non-stop flight included
Boise (BOI) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown 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)
Waldorf Astoria Chicago

Waldorf Astoria Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,293, price is now $772 per person
$772
per person
Dec 31 - Jan 3
found 12 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)

Sterling Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Hampton Inn & Suites Chicago Medical District UIC

Hampton Inn & Suites Chicago Medical District UIC

2.5 out of 5
Near West Side
Save 100% on your flight
Price was $671, price is now $367 per person
$367
per person
Nov 25 - Dec 2
found 20 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was $1,226, price is now $606 per person
$606
per person
Nov 25 - Dec 2
found 20 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Price was $2,445, price is now $1,340 per person
$1,340
per person
Nov 28 - Dec 3
found 15 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was $1,218, price is now $670 per person
$670
per person
Jan 12 - Jan 17
found 1 day 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
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
Select American Airlines flight, departing Thu, Dec 11 from Harry Reid Intl. to Greater Rockford, returning Mon, Dec 15, priced at $141 found 1 day ago
American Airlines
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
Select American Airlines flight, departing Tue, Nov 18 from Austin-Bergstrom Intl. to Quad City Intl., returning Sat, Dec 6, priced at $194 found 1 day ago
Bargain Flight
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
Select Bargain Flight flight, departing Tue, Oct 21 from Hartsfield-Jackson Atlanta Intl. to Greater Peoria Regional, returning Sun, Oct 26, priced at $238 found 2 days ago
Bargain Flight
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
Select Bargain Flight flight, departing Wed, Oct 29 from Seattle - Tacoma Intl. to Greater Peoria Regional, returning Sat, Nov 1, priced at $282 found 5 days ago