Route guide · 893 miles
Cheap Flights from Denver to Chicago
DEN → MDW · Nonstop 2h 19m · Live round-trip fares
Looking for cheap flights from Denver to Chicago? You're in the right place. Flyzento tracks live fares on this 893-mile route around the clock. As a rule of thumb, booking 3–6 weeks ahead lands the best prices — and a free fare alert means you never have to keep refreshing the page.
Live fares for DEN → MDW are updating. Use the search below for real-time prices.
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Updated daily
Flight time
2h 19m
Nonstop, typical
Distance
893 mi
DEN → MDW
Cheapest month
November 2026
Fares from $98
Nonstop airlines
2
Frontier Airlines, Southwest Airlines
Nonstop flights from Denver to Chicago
Nonstop service links Denver and Chicago directly — flights are flown by Frontier Airlines, Southwest Airlines. Expect roughly 2h 19m in the air. If a nonstop is what you want, don't wait too long: booking 3–6 weeks ahead is when these seats are priced most kindly.
Booking insights: Denver → Chicago
- Distance: 893 miles · nonstop flight time: 2h 19m.
- Cheapest upcoming week in the live data starts around Nov 25, with fares from $98.
- Of the months we're tracking right now, November 2026 has the lowest fares, starting at $98.
- 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 Flyzento alert instead of checking daily — the best fares can sell out in hours.
Price trend
Cheapest departure weeks ahead
Departing around Nov 25 is currently the cheapest window — about $89 less than the nearest weeks. Based on recent fares found for this route; prices change quickly.
Cheapest month · Denver → Chicago
November 2026
Every date's recent round-trip fare, at a glance.
Fares from
$98
Cheapest: Wed, Nov 25 — $98 · Priciest: Nov 14 — $264
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 Denver to Chicago: what you need to know
The flight
Denver to Chicago covers 893 miles, and a nonstop gets it done in about 2h 19m. That's long enough to settle in with a coffee and a downloaded show, short enough that a connection rarely makes sense — a layover usually doubles your travel day to save very little.
Airlines on this route
Frontier Airlines and Southwest Airlines fly 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 Denver (DEN)
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 Denver 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 Denver fares — prices on the return direction often move on a different rhythm.
When to book
Of the months we're currently tracking, November 2026 is coming in cheapest for this route, with fares from $98. As a rule, booking 3–6 weeks ahead lands you in the sweet spot — leave it to the final two weeks and prices usually climb. If you see a fare that works, don't wait around: set a fare alert on this page and we'll watch the price for you.
Good to know before you go
- 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.
- Nonstop time on this route is about 2h 19m — a one-stop itinerary needs to be a lot cheaper to be worth the extra hours.
Denver to Chicago flight FAQs
How long is the flight from DEN to MDW?
Plan on about 2h 19m in the air for a nonstop from Denver to Chicago — the route runs roughly 893 miles. Connecting flights typically add 2–4 hours.
Are there nonstop flights from Denver to Chicago?
Yes — look for Frontier Airlines, Southwest Airlines on this route. Nonstop seats are usually priced best 3–6 weeks before departure.
What is the cheapest month to fly from Denver to Chicago?
Of the months we're tracking right now, November 2026 has the lowest fares from Denver to Chicago, starting at $98. Fares update as new data comes in, so it's worth setting a free alert for your dates.
How much are last minute flights from DEN to MDW?
Book inside the final week and you'll usually pay a premium on DEN to MDW. Fares booked 3–6 weeks ahead are almost always kinder.
What is a good round-trip deal from Denver to Chicago?
A good deal is anything at or below the recent fares shown above. Set a free Flyzento alert and we'll ping you the moment fares drop.
Which airlines fly from Denver to Chicago?
The main carriers on this route are Frontier Airlines, 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 Denver 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 Denver
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