PGD to MDW – Explore Chicago

Visit Chicago with low-cost nonstop Allegiant flights from PGD to MDW!

Ranked the No. 1 Best Big City in the U.S., there are endless adventures to explore in Chicago. Catch a show from one of over 250 theaters, more than any other city in the U.S. Paddle through a canyon of skyscrapers on a guided kayak tour through the Chicago Riverwalk. View the biggest, best-preserved and most complete T. Rex fossil in the world at The Field Museum!

Culture & Performing Arts:

At Millennium Park, capture the perfect moment of your group reflected in the shiny Cloud Gate sculpture (aka The Bean). Splash around the multimedia Crown Fountain and watch a concert at the architecturally stunning Jay Pritzker Pavilion. At Skydeck Chicago, enjoy the interactive museum on the lower level and then take the high-speed elevator to The Ledge. The Ledge exhibits breathtaking views of the city from a glass-floored balcony.

Catch a Broadway in Chicago performance at one of Chicago’s historic downtown theaters. Classical music fans can see a Chicago Symphony Orchestra performance at the Symphony Center. Classical and contemporary ballets performed by world-renowned Joffrey Ballet are offered at the Lyric Opera of Chicago. For a night of laughter, attend an improv comedy show at The Second City.

Outdoor Adventures:

Whether you’re traveling by kayak or aboard Chicago’s First Lady, there are many ways to discover the Chicago Riverwalk, home to popular riverside attractions and cafes. Tackle the 40-foot rock climbing wall, rollerblade or ice skate in the winter through Maggie Daley Park, where there is fun for the whole family. Ride the sky-high Centennial Wheel, an old-fashioned carousel that offers 360-degree views of the city. For all the thrill-seekers, don’t miss the new FlyOver at Pier Park or a Seadog Speedboat tour. Nature lovers can escape the hustle and bustle of the city by hiking the nature trails at Northerly Island, a picturesque peninsula that overlooks Lake Michigan.

Foodie Paradise:

Visiting Chicago for the first time? You must try the classics. Chicago is best known for its deep-dish pizza, Chicago-style hot dogs and mile-high ice cream cones. Indulge in a thicky flaky crust, filled to the brim with cheese and topped with chunky tomato sauce at Uno Pizzeria, the birthplace of deep-dish pizza. Enjoy an all-beef hot dog on a poppy seed bun, topped with yellow mustard, relish, onions, tomatoes, a pickle spear, sport peppers and a dash of celery salt. Experience this Chicago tradition at Portillo’s in the Loop and Dave’s Red Hot. The Original Rainbow Cone tastes just as good as it looks. This classic Chicago treat is a cake cone piled high with chocolate, strawberry, vanilla with cherries and walnuts, pistachio and orange sherbet.

Looking for upscale food options? You’re in luck! In 2023, there were 22 Chicago restaurants awarded Michelin star honors. Treat your taste buds to modernist cuisine at Alinea, named the Best Restaurant in the World by Elite Traveler. Delve into a two-hour tasting event like never before at Ever. You’ll discover an eight- to 10-course tasting menu focusing on land and sea proteins with seasonal vegetables, paired with the perfect wine.

With an award-winning arts scene, one-of-a-kind attractions and iconic foods, Chicago is a must-see destination. Plan your trip today to embark on an unforgettable journey!