Cheap Flights from Ann Arbor (ARB) to Chicago (MDW)

Popular airlines from Ann Arbor, MI (ARB-Ann Arbor Municipal) to Chicago Midway Airport (MDW)

  • notification illustration

    Be in the know

    Get alerts if flight prices drop or rise*
  • deals illustration

    Book smarter

    Save up to 30% on select hotels after you book a flight*
  • trophy illustration

    Earn twice

    Earn your airline miles on top of our OneKeyCash
    Learn about One Key

Frequently asked questions

How much does a flight from Ann Arbor, MI (ARB-Ann Arbor Municipal) to Midway Intl. Airport (MDW) cost?
Grab a cheap one-way flight or cheap return flight from Ann Arbor, MI (ARB-Ann Arbor Municipal) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight offers on this route.
What is the cheapest month to fly from Ann Arbor, MI (ARB-Ann Arbor Municipal) to Midway Intl. Airport (MDW)?
is the least expensive month to fly from ARB to MDW. Planning your trip for the off-season is often the key to finding better fares.
Which airlines fly direct from Ann Arbor, MI (ARB-Ann Arbor Municipal) to Midway Intl. Airport (MDW)?
You can't catch a nonstop flight from Ann Arbor, MI (ARB-Ann Arbor Municipal) to Midway Intl. Airport (MDW). However, you can seamlessly travel to Chicago without any layovers by leaving from Detroit Metropolitan Wayne County Airport (DTW).
What is the cheapest airline that flies from Ann Arbor, MI (ARB-Ann Arbor Municipal) to Midway Intl. Airport (MDW)?
Use the filter tool on Expedia to compare airlines and find the most affordable carrier that'll fly you from ARB to MDW. Then, sort your results by "Price (lowest to highest)" to score a good deal.
How many flights per day from Ann Arbor, MI (ARB-Ann Arbor Municipal) to Midway Intl. Airport (MDW)?
There are no daily direct flights available from Ann Arbor, MI (ARB-Ann Arbor Municipal) to Midway Intl. Airport (MDW). But you can book flights with layovers. Filter your search results on Expedia to include one or two stops, and you'll be cruising above the clouds in no time at all.
What day of the week has the most flights from ARB to MDW?
Usually you'll find the widest variety of flight choices on a Friday. Tuesdays tend to be the quietest.* However, this can change depending on the airline, season and other factors.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Ann Arbor, MI (ARB-Ann Arbor Municipal) to Midway Intl. Airport (MDW)?
To avoid possible delays on the Ann Arbor, MI (ARB-Ann Arbor Municipal) to Midway Intl. Airport (MDW) route, aim to travel before 3 PM. Later departures have a 22% higher chance of being canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
Is it cheaper to buy a plane ticket from Ann Arbor, MI (ARB-Ann Arbor Municipal) to Midway Intl. Airport (MDW) last-minute?
Booking your ticket from ARB to MDW just before your trip is usually more expensive. But if there's some wiggle room with your travel dates and times, you could score a cheap last-minute fare.
Is it cheaper to book an ARB to MDW flight and hotel package?
Compared with arranging flights and hotels separately, booking an ARB to MDW flight and hotel package with Expedia could lead to significant savings. What's more, managing everything in one place will take the hassle out of travel planning. Just secure your flights and choose from our wide range of stays, then personalize your trip with extras like tours, car rentals and activities.
Can I cancel or change the date of my flight from Ann Arbor, MI (ARB-Ann Arbor Municipal) to Midway Intl. Airport (MDW)?
If you booked your ARB to MDW flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the fare type you purchased, additional charges may apply for changes beyond that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, visit our Customer Service portal if you want more information.

Travel information

Origin airport
Ann Arbor Municipal
Destination airport
Midway Intl.
Distance
207 mi

Book with confidence

Ann Arbor to Chicago Flights

The cheapest times to fly from Ann Arbor to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Ann Arbor to Chicago are during the month of . You can find some of the cheapest flights from Ann Arbor to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Ann Arbor to Chicago

Sunday is one of the best days to book for cheap flights from Ann Arbor to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Ann Arbor to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Ann Arbor to Chicago in 2026. You can also book with separate airlines for your outbound and return journeys, from one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Ann Arbor to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Ann Arbor to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Ann Arbor to Chicago Flights

Explore a world of travel with Expedia

*Available to One Key members.