Chicago—The famous 'Windy City' in the midwest. Many people who live in Illinois or the neighboring states of Wisconsin, Indiana, and Michigan use Chicago as their main base for airport departures. Chicago offers great domestic flights serving as a major hub for star alliance members United and American. Chicago O'Hare and Midway also offer great international flights with some of the cheapest fares to Europe and Africa. Below we've compiled the best weekend getaways and the best flight deals departing the Chicago metropolitan area. Whether you're looking for a solo trip, group getaway, or a nice family vacation we have you covered!
Call another region in the United States home? Check out the other departure regions that we commonly offer deals from.
In the Chicago metropolitan area, you'll find Chicago Midway International Airport (MDW) and O'Hare International Airport (ORD) offer a lot of great international and domestic flight deals with airlines such as Aer Lingus, TAP Air Portugal, Scandinavian Airlines, and Icelandair often offering affordable fares to Europe. Other airports include DuPage Airport Authority (DPA) and Chicago Rockford International Airport (RFD), which also offer commercial flights at a smaller scale.
Looking for a change of scenery from bustling Chicago? Venture away for a long weekend to the following locations. These spots are within easy reach of the city and offer a splendid weekend getaway for groups, couples, or families, alike. Or jet-off to Europe with great-value flight deals.
Looking for another city trip? Milwaukee might offer the perfect weekend trip. A roughly an hour and thirty five minute drive from Chicago. Milwaukee offers activities for the whole family. With great beer breweries for the adults to museums for the kids. There are also sandy beaches on the shoreline of Lake Michigan that are worth visiting.
The blueberry capital of the US and a roughly two hour drive from the 'Windy City', South Haven is a beautiful beach town in the neighboring state of Michigan. There are beautiful piers and lighthouses to visit.
Located on the Illinois river, Starved Rock is a state park that has canyons and waterfalls perfect for hiking and exploring. The park also offers great camping and glamping options for travelers from the big city of Chicago to disconnect from the hustle and bustle of city life and reconnect with nature.