Route guide · 1,729 miles
Cheap Flights from Seattle to Chicago
SEA → MDW · Nonstop 4h 1m · Live round-trip fares
The run from Seattle (SEA) to Chicago (MDW) is 1,729 miles of sky, and ticket prices on it are anything but steady. One week can cost double the next. Booking about 3–6 weeks in advance — and watching fares with a free Airfare Deal alert — is how regulars on this route keep costs down.
Live fares for SEA → MDW are updating. Use the search below for real-time prices.
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Updated daily
Flight time
4h 1m
Nonstop, typical
Distance
1,729 mi
SEA → MDW
Book ahead
3–6 weeks
Best window, typically
Nonstop airlines
1
Southwest Airlines
Nonstop flights from Seattle to Chicago
Want to skip the layover? Nonstops from Seattle to Chicago are flown by Southwest Airlines, getting you there in about 4h 1m. For the lowest fares, book around 3–6 weeks before departure — last-minute nonstops on this route rarely come cheap.
Booking insights: Seattle → Chicago
- Distance: 1,729 miles · nonstop flight time: 4h 1m.
- Cheapest upcoming week in the live data starts around Nov 5, with fares from $148.
- Rule of thumb for this route: the sweet spot is usually 3–6 weeks before departure.
- Midweek departures (Tue–Thu) are consistently cheaper than weekend flights.
- Set a free Airfare Deal alert instead of checking daily — the best fares can sell out in hours.
Cheapest month · Seattle → Chicago
November 2026
Every date's recent round-trip fare, at a glance.
Fares from
$148
Cheapest: Tue, Nov 10 — $148
Get this fare →Recent fares found for specific dates in November 2026. Blank days had no recent fare in our data — ask our team and we'll check them for you.
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Flying from Seattle to Chicago: what you need to know
The flight
Seattle to Chicago is a proper cross-country leg — 1,729 miles and around 4h 1m in the air nonstop. Download entertainment before you board, bring a full water bottle, and think about the time change: even a two-hour shift can leave you groggy if you land late and start early.
Airlines on this route
Southwest Airlines flies this route nonstop. That matters more than it sounds: the cheapest fare on one carrier is rarely the same product as the cheapest on another. Checked-bag fees, free seat selection and change rules all differ, so compare the full trip cost before you pick a winner. See our airline guides for exactly what each carrier charges — then send an enquiry and we'll confirm the all-in price for your dates.
Leaving from Seattle (SEA)
Plan to be at the airport two hours before a domestic departure — ninety minutes can work at smaller airports outside peak times, but security lines are the one variable you can't control. If you're checking a bag, add time rather than cutting it close. Our Seattle airport guide covers terminals, parking and ground transport so you can plan the trip to the airport, not just the flight.
Arriving in Chicago (MDW)
Before you land, know how you're getting from the airport to where you're staying — it's the part of the trip people forget to plan. The Chicago airport guide lays out your ground options, from transit and shuttles to rideshares and rental cars. Flying back the other way? Check Chicago to Seattle fares — prices on the return direction often move on a different rhythm.
When to book
For a trip of 1,729 miles, booking 3–6 weeks ahead typically lands you in the sweet spot. Leave it to the final two weeks and prices usually climb as the cheapest seats sell out. If your dates are flexible, midweek departures are where the lower fares hide on most domestic routes.
Good to know before you go
- Morning flights are delayed less often than evening ones — earlier departures have the best on-time record.
- Basic economy fares often exclude checked bags and seat selection. Price the whole trip, not the headline fare.
- Get to the airport two hours before departure; security, not the flight, is the part that runs late.
- If you're traveling with only a carry-on, you can skip the bag-drop line entirely with mobile check-in.
- Download the airline's app before you fly; gate changes and delays show up there first.
Seattle to Chicago flight FAQs
How long is the flight from SEA to MDW?
Plan on about 4h 1m in the air for a nonstop from Seattle to Chicago — the route runs roughly 1,729 miles. Connecting flights typically add 2–4 hours.
Are there nonstop flights from Seattle to Chicago?
Yes — look for Southwest Airlines on this route. Nonstop seats are usually priced best 3–6 weeks before departure.
What is the cheapest month to fly from Seattle to Chicago?
Fares from Seattle to Chicago tend to ease outside the peak summer and holiday rush — the late-summer and early-fall shoulder weeks are usually kinder on the wallet. Set a free Airfare Deal alert and we'll flag the dips for your dates.
How much are last minute flights from SEA to MDW?
Last-minute flights from SEA to MDW (booked within 7 days of departure) typically cost noticeably more than fares booked 3–6 weeks out. Booking early is the smarter move.
What is a good round-trip deal from Seattle to Chicago?
A good deal is anything at or below the recent fares shown above. Set a free Airfare Deal alert and we'll ping you the moment fares drop.
Which airlines fly from Seattle to Chicago?
The main carriers on this route are Southwest Airlines. Comparing all of them on the live search below usually surfaces the lowest fare for your dates.
How early should I get to Seattle airport for this flight?
Plan on two hours before departure for a domestic flight — ninety minutes can work at smaller airports outside peak times. If you're checking a bag, earlier is better; the bag-drop line, not the flight, is what runs late.
Do the cheapest fares on this route include a checked bag?
Usually not. Basic economy fares on most airlines include a carry-on but charge extra for checked bags, and seat selection can cost more too. Add up the real total before comparing — a slightly higher regular fare sometimes works out cheaper. Our team confirms the full breakdown with you before you pay.
More cheap flights from Seattle
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