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Addison Vacation Packages

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Addison Flight + Hotel Packages

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

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $504, price is now $280 per person
$280
per person
Feb 19 - Feb 23
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 – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
Price was $605, price is now $336 per person
$336
per person
Feb 19 - Feb 23
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.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Price was $1,168, price is now $652 per person
$652
per person
Feb 19 - Feb 23
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 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.
The Emily Hotel

The Emily Hotel

4 out of 5
Save 100% on your flight
Price was $699, price is now $414 per person
$414
per person
Mar 6 - Mar 10
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 a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions United Center and Chicago Riverwalk are located nearby.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Save 100% on your flight
Price was $793, price is now $470 per person
$470
per person
Mar 6 - Mar 10
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.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Save 100% on your flight
Price was $616, price is now $371 per person
$371
per person
Mar 6 - Mar 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, 2 bars/lounges, 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.
Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Save 100% on your flight
Price was $637, price is now $396 per person
$396
per person
Mar 6 - Mar 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Save 100% on your flight
Price was $524, price is now $326 per person
$326
per person
Mar 6 - Mar 10
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 24-hour fitness center, and valet parking (surcharge). Our guests praise the pool and the restaurant in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Addison 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
Save 100% on your flight
Price was $504, price is now $280 per person
$280
per person
Feb 19 - Feb 23
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 $605, price is now $336 per person
$336
per person
Feb 19 - Feb 23
found 1 day 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 $1,168, price is now $652 per person
$652
per person
Feb 19 - Feb 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $699, price is now $414 per person
$414
per person
Mar 6 - Mar 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

Addison Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $772, price is now $438 per person
$438
per person
Feb 26 - Mar 3
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,563, price is now $864 per person
$864
per person
Jan 23 - Jan 30
found 23 hours ago
Roundtrip non-stop flight included
Dallas (DAL) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was $1,514, price is now $845 per person
$845
per person
Feb 26 - Mar 3
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $924, price is now $529 per person
$529
per person
Jan 23 - Jan 30
found 23 hours ago
Roundtrip non-stop flight included
Dallas (DAL) to Chicago (ORD)

Top Flight Deals

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

United
Sat, Jan 17 - Sun, Jan 18
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$163 Roundtrip, found 1 day ago
$163
Roundtrip
found 1 day ago
Select United flight, departing Sat, Jan 17 from Los Angeles Intl. to O'Hare Intl., returning Sun, Jan 18, priced at $163 found 1 day ago
American Airlines
Sat, Feb 14 - Wed, Feb 18
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$163 Roundtrip, found 2 hours ago
$163
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Sat, Feb 14 from Los Angeles Intl. to O'Hare Intl., returning Wed, Feb 18, priced at $163 found 2 hours ago
Frontier Airlines
Thu, Jan 8 - Thu, Jan 15
LAX
Los Angeles Intl.
MDW
Midway Intl.
$194 Roundtrip, found 16 hours ago
$194
Roundtrip
found 16 hours ago
Select Frontier Airlines flight, departing Thu, Jan 8 from Los Angeles Intl. to Midway Intl., returning Thu, Jan 15, priced at $194 found 16 hours ago
Cathay Pacific
Thu, May 14 - Sat, May 30
PVG
Pudong Intl.
ORD
O'Hare Intl.
$1,172 Roundtrip, found 14 hours ago
$1,172
Roundtrip
found 14 hours ago
Select Cathay Pacific flight, departing Thu, May 14 from Pudong Intl. to O'Hare Intl., returning Sat, May 30, priced at $1,172 found 14 hours ago