Plan your trip to Chicago at least 6 weeks in advance. Doing so allows you to maximize options, in terms of flight dates, schedules and landing times. If you start looking for flights to Chicago at the last minute, you may be forced to accept layovers and round-trip fares above $500.
Identify low-cost airlines that fly into Chicago regularly. For Chicago, popular low-cost airlines include Southwest, AirTran and Jet Blue. Southwest and AirTran planes land at Midway, while JetBlue flies into O'Hare.
Search for cheap plane tickets to Chicago through low-cost carrier websites. Southwest, AirTran and JetBlue all feature easy-to-use online interfaces that sort plane tickets according to destination, schedule and costs. Toggle through each website to buy the two one-way tickets that combine together as the cheapest round trip fare.
Select a favored low-cost airline carrier to do business with over the long-term. All major airlines feature rewards programs that offer discounts to regular customers. After signing up, you may be targeted with special deals on flights to Chicago.
Hire a travel agent to put together an all-inclusive vacation package, if necessary. A good agent can leverage his contacts to cut costs on Lake Michigan cruises, Chicago Theatre District plays, car rentals and air travel into the Windy City.
