Published by Anne McDermott on July 3, 2023

Cheap Flights to Chicago: Best Days to Travel and Other Tips

Take in a game at Wrigley, travel the Loop on the El, jog the lakefront, shop on the Magnificent Mile or just sink your teeth into some of the best deep dish pizza in the world.

Chicago: Tourism, Attractions, Dining and Deals

So how do you get to this fabulous metropolis for less? That's where FareCompare comes in. Here are some tried-and-true ways to save on airfare to Chicago.

Cheapest Days to Fly to Chicago

The more of these tips you try, the more you'll save.

Cheapest Days to Fly

The cheapest days to fly to Chicago are typically Tuesday, Wednesday, and Saturday and sometimes Thursdays (since higher paying business travelers typically fly there on Sundays or Mondays and return home on Friday). Look for discounts and hotel deals for weekend stays in Chicago.

Cheapest Time of Day to Fly

The cheapest times to fly to Chicago are usually the times most of us don't want to fly: overnights or red-eyes, plus dawn flights and flights during the late evening.

Cheapest Time of Year to Fly

Chicago is a popular destination much of the year, but it can be cheaper during the frigid winter months, especially just before and after the Christmas/New Year's holiday period.

Chicago Airports: What You Need to Know

Chicago is served by two major airports, O'Hare and Midway.

Chicago O'Hare International (ORD): Located 17 miles from the Loop, this huge facility is served by numerous international and legacy carriers, plus discount airlines including JetBlue, Spirit and Virgin America.

Chicago Midway International (MDW):This smaller facility is just 10 miles from downtown and is dominated by Southwest Airlines; other major airlines include AirTran and Delta.

Airport Wi-Fi and Transportation

WiFi at Chicago Airports: Connections are available at both airports for a fee.

Transportation at Chicago Airports: Taxis, buses and shuttles are available but for efficiency and value, many travelers prefer the train; the Chicago Transit Authority's "Blue Line" for O'Hare and the "Orange Line" to/from Midway.

Getting Deals for Weekend Getaways and Last Minute Flights

If a weekend getaway to Chicago sounds good to you, take a look at these quick tips:

Sign up for FareCompare Airfare Alerts: We do the work for you by sending you real-time airfare alerts when prices to Chicago change; prices from your home airport. Note: You must open any alerts immediately as the cheapest seats are snapped up quickly.

Use the FareCompare Getaway Map: Perfect for last minute planning, the Getaway Map shows you instant airfares to Chicago from your own airport. The map also allows you to share any deals you find on Twitter.