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 DTW to MDW Flights

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Windsor

$291.73

Chicago

$138.40

Cheap DTW to MDW Flights

Question : From Detroit to Chicago, which day of the week is going to have the most flight times?
Answer : With 25 total flight time options, Tuesday provides the most flexibility from DTW to MDW. Sunday currently offers the least amount of flight times with 16 options.

Question : What's the likelihood of you being delayed on this route?
Answer : Using the combined on-time percentage and average delay breakdown, Detroit to Chicago currently has a 3 out of a possible 5 star rating. A 3-star rating means you should feel slightly worried about getting to Chicago on time.

Question : Which airline is least likely to get you to MDW on time?
Answer : If you decide to book your flight with Air Canada, keep an eye on your departure time. 100% of flights from Detroit Metropolitan Wayne County Airport (DTW) to Chicago Midway International Airport (MDW) are delayed.

Question : Looking for the fastest flight from DTW to MDW?
Answer : If you're able to take the shortest direct flight (which is offered by Southwest Airlines), you will be able to leave DTW at 5:05 PM EST and get to MDW at 5:10 PM CST (one hour and five minutes). Remember, there is a one-hour time change.

Question : If traveling from DTW to MDW, how long can you expect to be in the air?
Answer : When flying from DTW to MDW, it will take one hour and 20 minutes on average.

Question : How often is the Detroit Metropolitan Wayne County Airport (DTW) to Chicago Midway International Airport (MDW) route delayed?
Answer : Flights from DTW to MDW are on time 79% of the time, ranking in the top 50% of the world. When there is a delay, it averages about half an hour.

Question : If punctuality is required for you to book a flight, which airline is your best bet?
Answer : Delta Air Lines leads the way with an 87% on-time rate. Stick to Delta Air Lines and you won't spend more time in airports than you have to. If they are delayed for some reason though, the average delay is less than 15 minutes.

Detroit 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 Detroit 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 DTW to MDW flights that won’t make your bank account wince. Ready to temporarily leave behind Detroit 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.