We value your privacy

We use cookies to enhance your browsing experience, serve personalized content, and analyze our traffic. By clicking "Accept All" you accept this and consent that we share this information with third parties and that your data may be processed in the USA. For more information, please read our .

You can adjust your preferences at any time. If you deny, we will use only the essential cookies and unfortunately, you will not receive any personalized content. To deny, .

Deals on Flights & Vacations Departing from the Chicago Metropolitan Area

Chicago Metropolitan Area 🌆: Travel for Those Located in and around the Chicago Area

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.

Cheap Flight Destinations from Chicago

Below, we've compiled a list of international destinations you can frequently fly cheaply to out of the Chicago area.


Chicago is one of the cheaper places in the US to fly out from to get to the continent of Africa. When gathering flights to Kenya, we find that Chicago offers often the second or lowest price point and we have seen flights to Kenya as low as in the $500s for a round-trip fare.


One of the major airports that TAP Air Portugal flies out of in the US, oftentimes, we'll find great-value and full-service flights to major cities in Portugal and to the Azores Islands. We've seen fares as low as in the $300s for flights to Portugal and back.


Comprising of Norway, Sweden, Finland, and Copenhagen, we often find great flight deals through the full-service airline Scandinavian Airlines or budget airline, Norse Atlantic Airways. We've seen flights as low as the $300s round trip.


From Chicago, you can fly to our neighbor in the south for quite cheap with budget airlines like Spirit and Frontier. For just a bit more you can also find great-value flights with full-service airlines like American, JetBlue, United, and Delta. Cheap flight destinations in Mexico include Cancun, Mexico City, and Puerto Vallarta just to name a few.

The Best Weekend Trips from Chicago

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.

Milwaukee, Wisconsin

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.

South Haven, Michigan

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.

Lake Geneva, Wisconsin

Home to breathtaking mansions and a plethora of luxury resorts, Lake Geneva isn't only a great summer spot but offers great winter activities including one of the five ice castle experiences in the US.

Starved Rock State Park, Illinois

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.