Beginning of main content
Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5

Search over 321,000 hotels worldwide and 400 airlines worldwide.

Secure incredible value with Expedia's Price Guarantee.

No Expedia cancellation fee to change or cancel almost any hotel reservation.

Cheap ORD to MDW Flights

Question : If punctuality is required for you to book a flight, which airline is your best bet?
Answer : American Airlines leads the way with a 100% on-time rate. Spend as little time in an airport as necessary by flying with American Airlines. Perfection is hard to come by, so hopefully it continues.

Question : How often is the O'Hare International Airport (ORD) to Chicago Midway International Airport (MDW) route delayed?
Answer : The Chicago to Chicago route has a 60% on-time rate, ranking in the 45th percentile worldwide in getting their passengers to their destinations on schedule. If a flight is late, though, expect an average of about half an hour added to your flight time.

Question : What's the likelihood of you being delayed on this route?
Answer : ORD to MDW currently scores 2 out of a possible 5 stars in promptness. This score combines both the number of delayed flights and total delay minutes. With 2 stars, you should feel rather worried about getting to Chicago on time.

Question : Which airline can you expect delays with on this route?
Answer : Flexjet is delayed on 100% of flights from O'Hare International Airport (ORD) to Chicago Midway International Airport (MDW) at the moment. If you’re on Flexjet, be sure to sign up for the delay notifications to stay up to date with your flight’s status.

Chicago to Chicago Flights

Sometimes you just need to get out of town or maybe you’re looking for a change of scenery. Regardless of the reason, a flight from Chicago to Chicago will do just the trick! Go on, plan to see all the famous landmarks and eat your weight in the local cuisine. Your trip is beckoning, so answer the call by packing your suitcase and filling your travel itinerary with exploring Chicago.

Whether you’re flying for business or jet-setting on your personal time, you’ve come to the right place. Here at Expedia.com, we’ll pair you up with ORD to MDW flights that won’t make your bank account wince. Ready to temporarily leave behind Chicago for new horizons? Browse through our cheap airfare, and filter by flight times and dates until you find just what you had in mind. From flights without layovers to ones that arrive early in the morning, you’ll come across plane tickets that suit your travel preferences. You can even bundle your flight to MDW with hotels and car rentals to score even bigger savings.

All set to hit the clouds? Book your travel arrangements with us today and have left-over money to put toward your travel outings and adventures.