Somethings in Life Are Just Better Together

Peanut butter and Jelly, Sun and sand, skis and snow. Somethings in life are just better together like bunding your flight and hotel. And when you add features like sightseeing, tours, attractions and a rental car you can do more and save more. So take the tour, drop the top or share an adventure all on one itinerary.


Customized vacation packages include:

  • Round trip flight via Southwest Airlines®.
  • Hotel accommodations (including taxes).
  • Bags fly free® with Southwest Vacations®. Even golf bags fly free®.


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Shop featured hotels to complete your package


Palamar Chicago Kimpton Star Rating

Complimentary daily breakfast + room upgrade

Guests receive two complimentary continental breakfast vouchers per day.
  • Room upgrade to the next available room category is based on availability and will be assigned at time of check-in.
  • Hotel offer blackout dates: 6/26/19 – 7/9/19.

Doubletree By Hilton Hotel Chicago Magnificent Mile

Star Rating

 Just three blocks west of Navy Pier and two blocks east of the world-renown shopping, dining and entertainment lining Michigan Avenue, this appealing Chicago hotel provides comfortable accommodations in a great location.


Palmer House, A Hilton Hotel Star Rating


 Where old world elegance blends with the modern amenities of today, this inspired hotel offers luxury travelers, spa-lovers and shopping-enthusiasts with an upscale oasis in the heart of sweet home Chicago.


The Westin Michigan Avenue Chicago

Star Rating

 The Westin Michagan Avenue Chicago located on Chicago's famed Magnificent Mile, is steps from Lake Michigan, Michigan Avenue restaurants and premier Michigan Avenue shopping.


Hyatt Regency Chicago

Star Rating


Discover the difference and experience the sophistication at our downtown Chicago hotel. Set within the epicenter of the Windy City, our AAA Four Diamond Hyatt Regency Chicago is conveniently connected to the Illinois Center and located steps away from the Magnificent Mile


The Drake, A Hilton Hotel

Star Rating


 Additional Values

Hilton Chicago

Star Rating



Sheraton Grand Chicago

Star Rating


 Offering spectacular views of the Chicago River, Lake Michigan or the city skyline, this grand hotel is one of Chicago's superior riverfront destinations.


Chicago Marriott Downtown Magnificent Mile

Star Rating

Additional Values

Stay and Save Free Night

Encounter a renowned Chicago hotel combining the epitome of luxury and convenience at the Marriott Downtown Chicago Magnificent Mile Hotel, a Windy City landmark on Michigan Avenue's Magnificent Mile.


Thompson Chicago

Star Rating

Our "El"-evated Chicago Boutique Hotel
British design icon Tara Bernerd turns her worldly, eclectic sensibility to eleven, with the loft-like, urban industrial bones of the lobby and lounge accented with warm American woods and clean, mid-century lines throughout our unique downtown Chicago hotel on the Gold Coast.


Swissotel Chicago

Star Rating

Designed by noted city architect Harry Weese- and in a class all its own- Swissotel Chicago rises above the point where the Chicago River meets Lake Michigan.


Loews Chicago Hotel

Star Rating


Newly opened in March 2015 - Loews Chicago Hotel - located in Streeterville - one block north of the Chicago River and two blocks east of Michigan Avenue.


Omni Chicago Hotel

Star Rating


Additional Values


The Omni Chicago is Michigan Avenues only all suite luxury hotel. Located in the heart of the Magnificent Mile, surrounded by world class shopping, exciting entertainment, museums and galleries this hotel combines luxury and sophistication.




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Call 866-547-5362 for more information or to book today! Mention code 14245268

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