From stunning skyline views to eclectic museums to lakefront fun, book a flight from Windsor to Chicago to discover one of the largest cities in the US, and a true wonder for anyone who loves architecture, art, and culture.
Savvy travellers will want to be in The Loop when it comes to Chicago attractions. The Loop is Chicago’s central business district, bordered by the L train, which runs above its busy streets.
Here you’ll find countless Chicago attractions including outdoor sculptures, an historic theatre district, and Millennium Park. This futuristic park seamlessly combines expansive lawns with contemporary architecture.
Make your way under the archway of “Cloud Gate.” This famous elliptical structure, fondly known as “The Bean,” has a shiny silver surface that reflects visitors and the spectacular skyline in the background.
Across the way, you’ll find The Art Institute of Chicago. The building is a work of art itself with Beaux-Arts architecture and watchful bronze lions at its front steps. The Art Institute features European, American and Asian collections.
At the waterfront section of The Loop spend some time by the lake at Navy Pier. First opened in 1916, Navy Pier now keeps the crowds amused with shopping, dining, and entertainment.
South of Navy Pier, The Field Museum of Natural History gives a mighty roar with the largest and most intact T. Rex skeleton on earth. A little farther south at the beloved Museum of Science and Industry, interactive exhibits educate and entertain, delighting curious minds of all ages.
Grown ups are sure to have a good time in Chicago after dark. Chicago’s jazz, blues and theatre filled nightlife is worth a toast.
Book a flight from Windsor to Chicago and brace yourself. The Windy City is sure to blow you away.
Book flights from Windsor to Chicago and discover Roscoe Village, a quiet pocket of restaurants, shops, and friendly locals. Roscoe Village proudly flaunts its title as “the village within the city” on its hand-painted welcome sign.
These words ring true with an almost palpable tight-knit community feel. Many decades-old mainstays remain family owned and flourishing in this cozy neighbourhood.
With independent businesses, antique shops, vintage clothing stores, funky boutiques, and more this walkable neighbourhood has a distinctly different feel and pace from Chicago’s main tourist attractions.
Whether you’re craving authentic Turkish cuisine, deep dish pizza with homemade sauce, Mexican dishes, or Guatemalan stews, Roscoe Village will satisfy your appetite. It’s also the perfect place for a drink with laid-back libations and friendly service on sidewalk and rooftop patios.
Don’t tap out before hitting up The Village Tap, a decades-old mainstay and the first neighbourhood tap in Roscoe Village. They were one of the first establishments to get behind the craft beer movement and pride themselves on being a local favourite with hospitality, a casual atmosphere, varied menu, and one of Chicago’s best beer gardens.
You’ll feel right at home at John’s Place with home-style food and a casual atmosphere. This Roscoe Village mainstay has been serving up delicious dishes and friendly service since the early 90s. Today, it’s still a popular casual spot and weekend brunch favourite for many.
Don’t let your food get cold. Book a flight from Windsor to Chicago to explore this quiet alcove tucked away on Chicago’s North Side, charming and quaint but brimming with activity.
Historically, Hyde Park has been the home of Chicago’s rich and famous. In 1893, Hyde Park became known for hosting the Chicago World’s Fair also known as The Columbian Exposition, which introduced the nation to electricity.
Its more recent claim to fame is being the former home of President Barack Obama. Although not allowed inside, tourists flock to the area to get an outside view of his Georgian revival house.
In the south-east corner of Hyde Park, all ages can get up close and personal with the wonders of The Museum of Science and Industry. It’s the largest science museum in the Western Hemisphere boasting over 2,000 exhibits, fascinating multimedia displays, interactive activities, and the largest and most intact T. Rex skeleton in the world.
Just steps away from the excitement of this museum’s mind-boggling wonders, you can take in some fresh air at Jackson Park along with lush sights at the Japanese-style Osaka Garden. From a quiet spot along Lake Michigan at Promontory Point, you can see downtown Chicago jutting out into the water from a distance.
Bookworms will want to bookmark this neighbourhood where you’ll find stacks of bookshops and coffeehouses, as well as the Victorian Gothic beauty of the University of Chicago.
History buffs should be sure to visit The DuSable Museum of African-American History. Founded in 1961, it houses galleries dedicated to African-American art, culture, and history. With over 15,000 paintings, sculptures, print works, and more, you’re sure to learn something new.
Back outside you can survey more of Hyde Park’s fascinating past and relaxed present with a bike tour. Book a flight from Windsor to Chicago and hide out in Hyde Park for a laid back look at some unique local history.
Fly from Windsor International Airport (YQG) to Chicago Midway International Airport (MDW), with a quick connection in Toronto. Windsor to Chicago flight time is 2 hours and 20 minutes on average. Connection times vary. The distance from Windsor to Chicago is around 1045 km / 650 mi.
Enjoy complimentary drinks and snacks along the way.
Porter’s check-in desk is located in the departures area.
Windsor International Airport (YQG) is about 10 km / 6 mi from downtown Windsor.
Please allow sufficient time to drop off your car rental before your departing flight.
Taxis from downtown cost about $25 CAD. Car service costs about $35 CAD.
Take the Transit Windsor 8 Walkerville bus to the airport stop. The fare is $3.00 CAD.
Chicago Midway International Airport (MDW) is about 9 km / 6 mi from downtown Chicago.
The Go Airport Express shuttle bus provides service from the airport to downtown. The fare is $27 USD.
Car rental services are available at Chicago Midway Airport (MDW). Take the shuttle to the rental car area from the pick-up location at door 3 of the lower level, near the baggage claim area.
Taxis to downtown cost about $20 USD per person. Car service is available.
Take the Chicago Transit Authority orange line from the Midway stop. The fare is $2.25 USD.
All prices are per person in Canadian dollars. Taxes and fees are included in the total package price. Prices and availability are not final until reservation is confirmed with payment. Baggage fees and other optional fees charged by Porter are not included.