$155 Cheap Flights from Redmond (RDM) to Chicago (MDW)

View $155 flight on Sat, Nov 22, 2025Opens in a new window

Popular airlines from Redmond Municipal Airport (RDM) to Chicago Midway Airport (MDW)

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Cheap Flights from Redmond to Chicago (RDM-MDW)

Prices were available within the past 7 days and start at $155 for one-way flights and $329 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Thu, Dec 4 - Mon, Dec 8
RDM
Redmond
MDW
Chicago
$329 Roundtrip, found 6 days ago
$329
Roundtrip
found 6 days ago
Select Delta flight, departing Thu, Dec 4 from Redmond to Chicago, returning Mon, Dec 8, priced at $329 found 6 days ago
Delta
Thu, Dec 4 - Mon, Dec 8
RDM
Redmond
MDW
Chicago
$389 Roundtrip, found 6 days ago
$389
Roundtrip
found 6 days ago
Select Delta flight, departing Thu, Dec 4 from Redmond to Chicago, returning Mon, Dec 8, priced at $389 found 6 days ago
Delta
Thu, Dec 4 - Mon, Dec 8
RDM
Redmond
MDW
Chicago
$419 Roundtrip, found 6 days ago
$419
Roundtrip
found 6 days ago
Select Delta flight, departing Thu, Dec 4 from Redmond to Chicago, returning Mon, Dec 8, priced at $419 found 6 days ago
Delta
Thu, Dec 4 - Mon, Dec 8
RDM
Redmond
MDW
Chicago
$429 Roundtrip, found 6 days ago
$429
Roundtrip
found 6 days ago
Select Delta flight, departing Thu, Dec 4 from Redmond to Chicago, returning Mon, Dec 8, priced at $429 found 6 days ago
Delta
Thu, Dec 4 - Mon, Dec 8
RDM
Redmond
MDW
Chicago
$479 Roundtrip, found 6 days ago
$479
Roundtrip
found 6 days ago
Select Delta flight, departing Thu, Dec 4 from Redmond to Chicago, returning Mon, Dec 8, priced at $479 found 6 days ago
Delta
Tue, Sep 30 - Thu, Oct 2
RDM
Redmond
MDW
Chicago
$507 Roundtrip, found 19 hours ago
$507
Roundtrip
found 19 hours ago
Select Delta flight, departing Tue, Sep 30 from Redmond to Chicago, returning Thu, Oct 2, priced at $507 found 19 hours ago
Delta
Tue, Sep 30 - Thu, Oct 2
RDM
Redmond
MDW
Chicago
$555 Roundtrip, found 19 hours ago
$555
Roundtrip
found 19 hours ago
Select Delta flight, departing Tue, Sep 30 from Redmond to Chicago, returning Thu, Oct 2, priced at $555 found 19 hours ago
Delta
Tue, Sep 30 - Thu, Oct 2
RDM
Redmond
MDW
Chicago
$597 Roundtrip, found 19 hours ago
$597
Roundtrip
found 19 hours ago
Select Delta flight, departing Tue, Sep 30 from Redmond to Chicago, returning Thu, Oct 2, priced at $597 found 19 hours ago
Delta
Tue, Sep 30 - Thu, Oct 2
RDM
Redmond
MDW
Chicago
$629 Roundtrip, found 19 hours ago
$629
Roundtrip
found 19 hours ago
Select Delta flight, departing Tue, Sep 30 from Redmond to Chicago, returning Thu, Oct 2, priced at $629 found 19 hours ago
Alaska Airlines
Tue, Sep 30 - Thu, Oct 2
RDM
Redmond
MDW
Chicago
$921 Roundtrip, found 19 hours ago
$921
Roundtrip
found 19 hours ago
Select Alaska Airlines flight, departing Tue, Sep 30 from Redmond to Chicago, returning Thu, Oct 2, priced at $921 found 19 hours ago

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $421
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $421

Frequently asked questions

How much does a flight from Robert's Field Airport (RDM) to Midway Intl. Airport (MDW) cost?
Grab a cheap one-way flight from $155 or cheap return flight from $329 from Robert's Field Airport (RDM) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight deals on this route.
What is the cheapest month to fly from Robert's Field Airport (RDM) to Midway Intl. Airport (MDW)?
December is the cheapest month to fly from RDM to MDW. Avoiding peak travel times is often the key to finding better deals on flights.
What is the cheapest airline that flies from Robert's Field Airport (RDM) to Midway Intl. Airport (MDW)?
Expedia's filter tool lets you easily compare travel time, airlines and fares all in one place. Choose your preferences, then sort by "Price (lowest to highest)" to find the carrier with the cheapest RDM to MDW flight.
How many flights per day from Robert's Field Airport (RDM) to Midway Intl. Airport (MDW)?
You'll have to take a flight with a layover if you're traveling from Robert's Field Airport (RDM) to Midway Intl. Airport (MDW). There are no daily direct flights on this route. However, just filter your search to include one or two stops to find an option that works for you.
What day of the week has the most flights from RDM to MDW?
You'll usually find Tuesday the quietest day for flights, while Fridays are often the busiest.* However this can vary from season to season and during public holidays or peak travel times.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Robert's Field Airport (RDM) to Midway Intl. Airport (MDW)?
To touch down at Midway Intl. Airport (MDW) on schedule, book a flight that takes off from Robert's Field Airport (RDM) before 3 PM. The likelihood of cancellations is 22% higher, on average, for departures after this time.**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 Robert's Field Airport (RDM) to Midway Intl. Airport (MDW) last-minute?
Booking your ticket from RDM to MDW shortly before your trip is usually more expensive. But if there's some wiggle room with your itinerary, you could land a cheap last-minute fare.
Is it cheaper to book a RDM to MDW flight and hotel package?
You can save money by securing a RDM to MDW flight and hotel package compared to booking separately. In fact, travelers could save hundreds of dollars by bundling with Expedia. And it's easy to manage everything in one convenient place. After selecting your ideal accommodations and flights, consider other add-ons like activities, tours and car rentals.
Can I cancel or change the date of my flight from Robert's Field Airport (RDM) to Midway Intl. Airport (MDW)?
In most instances, you can cancel or reschedule your RDM to MDW flight. However, additional charges may apply, especially if you made your booking over 24 hours ago. Double-check your itinerary for the airline's fees and policies on flight changes, or if you'd like further details, visit our Customer Service portal.

Travel information

Travel information

Origin airport
Robert's Field
Destination airport
Midway Intl.
Airlines serving
Delta
Roundtrip price
$329
Distance
1684 mi

Book with confidence

Book with confidence

Redmond to Chicago Flights

The cheapest times to fly from Redmond 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 Redmond to Chicago are during the month of December. You can find some of the cheapest flights from Redmond to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Redmond to Chicago

Sunday is one of the best days to book for cheap flights from Redmond 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 Redmond 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 Redmond to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $155 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 Redmond 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 Redmond 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.

 

Redmond to Chicago Flights

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