Route guide · 422 miles
Cheap Flights from Omaha to Chicago
OMA → MDW · Nonstop 1h 21m · Live round-trip fares
Flying from Omaha to Chicago doesn't have to drain your wallet. This 422-mile hop takes about 1h 21m nonstop, and fares swing a lot depending on the week you pick. Travelers who book roughly 2–4 weeks out usually come out ahead — set a free alert and let the deals come to you.
Live fares for OMA → MDW are updating. Use the search below for real-time prices.
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Updated daily
Flight time
1h 21m
Nonstop, typical
Distance
422 mi
OMA → MDW
Book ahead
2–4 weeks
Best window, typically
Nonstop airlines
1
Southwest Airlines
Nonstop flights from Omaha to Chicago
Nonstop service links Omaha and Chicago directly — flights are flown by Southwest Airlines. Expect roughly 1h 21m in the air. If a nonstop is what you want, don't wait too long: booking 2–4 weeks ahead is when these seats are priced most kindly.
Booking insights: Omaha → Chicago
- Distance: 422 miles · nonstop flight time: 1h 21m.
- Cheapest upcoming week in the live data starts around Oct 22, with fares from $227.
- Rule of thumb for this route: the sweet spot is usually 2–4 weeks before departure.
- If your dates flex by a day or two, shifting to a midweek departure is the easiest saving there is.
- Set a free Airfare Deal alert instead of checking daily — the best fares can sell out in hours.
Cheapest month · Omaha → Chicago
October 2026
Every date's recent round-trip fare, at a glance.
Fares from
$227
Cheapest: Mon, Oct 26 — $227
Get this fare →Recent fares found for specific dates in October 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 Omaha to Chicago: what you need to know
The flight
Omaha to Chicago is a short hop — 422 miles, about 1h 21m gate to gate on a nonstop. You'll spend almost as long taxiing and boarding as you will in the air, so the real time-saver on this route is picking flight times that dodge rush hour at both ends.
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 Omaha (OMA)
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 Omaha 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 Omaha fares — prices on the return direction often move on a different rhythm.
When to book
For a trip of 422 miles, booking 2–4 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
- 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.
- Nonstop time on this route is about 1h 21m — a one-stop itinerary needs to be a lot cheaper to be worth the extra hours.
- Tuesday and Wednesday departures are typically the cheapest days on domestic routes.
Omaha to Chicago flight FAQs
How long is the flight from OMA to MDW?
A nonstop from OMA to MDW clocks in at around 1h 21m for the 422-mile trip. If you're connecting, budget an extra 2–4 hours depending on where you stop.
Are there nonstop flights from Omaha to Chicago?
Yes — look for Southwest Airlines on this route. Nonstop seats are usually priced best 2–4 weeks before departure.
What is the cheapest month to fly from Omaha to Chicago?
There's no single magic month, but prices on this route generally soften in the shoulder season, when demand dips after the holidays and again in early fall. A free fare alert is the easiest way to catch those windows.
How much are last minute flights from OMA to MDW?
Walking up to this route at the last minute is the expensive way to do it — prices inside 7 days of departure climb fast. The 2–4 weeks booking window is where the value sits.
What is a good round-trip deal from Omaha 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 Omaha 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 Omaha 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.
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