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Cheap Flights from Chicago (MDW) to Denver (DEN)

Compare Chicago Midway to Denver International flight deals

Find the cheapest month or even day of the year to fly to Denver International

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Flight deals from Chicago Midway to Denver International

Looking for a cheap last-minute deal or the best return flight from Chicago Midway Airport to Denver International Airport? If you want to travel next month, return fares start from $295. Find the lowest prices on one-way and return tickets right here.
Denver.$295 per passenger.Departing Thu, 19 Nov, returning Thu, 26 Nov.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Thu, 19 Nov, arriving in Denver International.Inbound direct flight with Southwest Airlines departs from Denver International on Thu, 26 Nov, arriving in Chicago Midway.Price includes taxes and charges.From $295, select.
Denver.$295 per passenger.Departing Wed, 7 Oct, returning Sat, 10 Oct.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 7 Oct, arriving in Denver International.Inbound direct flight with Southwest Airlines departs from Denver International on Sat, 10 Oct, arriving in Chicago Midway.Price includes taxes and charges.From $295, select.
Denver.$295 per passenger.Departing Sat, 12 Sep, returning Wed, 16 Sep.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 12 Sep, arriving in Denver International.Inbound direct flight with Southwest Airlines departs from Denver International on Wed, 16 Sep, arriving in Chicago Midway.Price includes taxes and charges.From $295, select.
Denver.$295 per passenger.Departing Mon, 24 Aug, returning Thu, 27 Aug.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Mon, 24 Aug, arriving in Denver International.Inbound direct flight with Southwest Airlines departs from Denver International on Thu, 27 Aug, arriving in Chicago Midway.Price includes taxes and charges.From $295, select.
Denver.$295 per passenger.Departing Tue, 1 Dec, returning Tue, 8 Dec.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 1 Dec, arriving in Denver International.Inbound direct flight with Southwest Airlines departs from Denver International on Tue, 8 Dec, arriving in Chicago Midway.Price includes taxes and charges.From $295, select.
Denver.$295 per passenger.Departing Tue, 1 Sep, returning Thu, 1 Oct.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 1 Sep, arriving in Denver International.Inbound direct flight with Southwest Airlines departs from Denver International on Thu, 1 Oct, arriving in Chicago Midway.Price includes taxes and charges.From $295, select.
Denver.$295 per passenger.Departing Mon, 31 Aug, returning Wed, 30 Sep.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Mon, 31 Aug, arriving in Denver International.Inbound direct flight with Southwest Airlines departs from Denver International on Wed, 30 Sep, arriving in Chicago Midway.Price includes taxes and charges.From $295, select.
Denver.$307 per passenger.Departing Wed, 28 Oct, returning Wed, 4 Nov.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 28 Oct, arriving in Denver International.Inbound direct flight with Southwest Airlines departs from Denver International on Wed, 4 Nov, arriving in Chicago Midway.Price includes taxes and charges.From $307, select.
Denver.$307 per passenger.Departing Thu, 25 Feb, returning Thu, 25 Feb.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Thu, 25 Feb, arriving in Denver International.Inbound direct flight with Southwest Airlines departs from Denver International on Thu, 25 Feb, arriving in Chicago Midway.Price includes taxes and charges.From $307, select.
Denver.$307 per passenger.Departing Thu, 21 Jan, returning Mon, 25 Jan.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Thu, 21 Jan, arriving in Denver International.Inbound direct flight with Southwest Airlines departs from Denver International on Mon, 25 Jan, arriving in Chicago Midway.Price includes taxes and charges.From $307, select.
Denver.$322 per passenger.Departing Thu, 26 Nov, returning Tue, 1 Dec.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Thu, 26 Nov, arriving in Denver International.Inbound indirect flight with Southwest Airlines, departs from Denver International on Tue, 1 Dec, arriving in Chicago Midway.Price includes taxes and charges.From $322, select.
Denver.$338 per passenger.Departing Tue, 24 Nov, returning Tue, 1 Dec.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 24 Nov, arriving in Denver International.Inbound direct flight with Southwest Airlines departs from Denver International on Tue, 1 Dec, arriving in Chicago Midway.Price includes taxes and charges.From $338, select.
Denver.$353 per passenger.Departing Fri, 26 Feb, returning Tue, 2 Mar.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Fri, 26 Feb, arriving in Denver International.Inbound direct flight with Southwest Airlines departs from Denver International on Tue, 2 Mar, arriving in Chicago Midway.Price includes taxes and charges.From $353, select.
Denver.$353 per passenger.Departing Thu, 17 Dec, returning Mon, 4 Jan.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Thu, 17 Dec, arriving in Denver International.Inbound direct flight with Southwest Airlines departs from Denver International on Mon, 4 Jan, arriving in Chicago Midway.Price includes taxes and charges.From $353, select.
Denver.$355 per passenger.Departing Fri, 28 Aug, returning Sat, 10 Oct.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago Midway on Fri, 28 Aug, arriving in Denver International.Inbound indirect flight with Frontier Airlines, departs from Denver International on Sat, 10 Oct, arriving in Chicago Midway.Price includes taxes and charges.From $355, select.
Denver.$382 per passenger.Departing Fri, 5 Mar, returning Wed, 10 Mar.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Fri, 5 Mar, arriving in Denver International.Inbound direct flight with Southwest Airlines departs from Denver International on Wed, 10 Mar, arriving in Chicago Midway.Price includes taxes and charges.From $382, select.

Find the cheapest month to fly from Chicago Midway to Denver International

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Chicago Midway to Denver International flights are currently cheapest in August.
Jul
from $457
Aug
from $295
Sep
from $295
Oct
from $295
Nov
from $295
Dec
from $295
Jan
from $307
Feb
from $307
Mar
from $382
Apr
from $457
May
from $488
Jun
from $437

Direct flights from Chicago Midway to Denver International

Chicago Midway to Denver International: Alternative routes

Compare routes from Chicago Midway to Denver below. You may find an airport to fly into that's cheaper, faster, or easier than Denver International.

Denver International

30km from central Denver
ClosestCheapest
from $295
Search flights

Chicago to Denver: Flight information

The things to know before you go.
Cheapest flight found$295
Cheapest month to flyNovember
Average flight time2 hrs, 41 mins
Most popular airlineSouthwest Airlines
Average flights per week64

Finding cheap flights from Chicago Midway to Denver International: Frequently asked questions

The best price we found for a return flight from Chicago Midway to Denver International is $295. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
2 hours and 41 minutes is the average flight time from Chicago Midway to Denver International.
Southwest Airlines flies direct from Chicago Midway to Denver International.
As of July 2026, there are 64 flights per week flying from Chicago Midway to Denver International.
The cheapest month to fly from Chicago Midway to Denver International is usually November.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Chicago Midway Airport to Denver International Airport on Thursday, 19 November 2026.
Yes – the average flight time is 2 hours and 41 minutes.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Denver International but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.

We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Denver is around 40 days in advance, so don’t leave your flight to the last minute.

Currently, Southwest Airlines offers the cheapest flight tickets to Denver International.

Travelling from Chicago Midway Airport (MDW) to Denver International Airport (DEN): what you need to know

  • Around 2 hours 40 minutes is how long you can expect to be in the air on a direct flight from Chicago Midway Airport to Denver International Airport.

  • Denver's timezone is UTC-7, making Denver one hour behind Chicago.

  • Take your pick of 26 weekly Chicago Midway Airport to Denver International Airport flights. The 05:10 departure with Southwest Airlines is the earliest flight you can take. Southwest Airlines operates the latest service of the day at 22:55.

  • To ensure you catch your MDW to DEN flight, allow plenty of time to navigate the airport and find your gate. Arriving two hours before international departures and one hour before domestic flights is the general rule.

  • During popular months like July, it's best to get to the airport earlier. Arrive two hours before domestic departures and four hours ahead of international flights when you travel during a high season in general.

  • Southwest Airlines is your gateway to exploring Denver (and maybe even some other exciting corners of the United States!). Browse the direct flights from Chicago Midway Airport to Denver International Airport offered by this carrier.

  • The majority of passengers choose to travel with Southwest Airlines on this route.

  • With an impressive 80.43% of services arriving as planned, Frontier Airlines has the best on-time performance for MDW to DEN flights.

  • Consider adding a stopover when booking your ticket from Chicago Midway Airport to Denver International Airport. Just deselect 'Direct flights only' to break up your journey, or even explore someplace new along the way. Here are some options between MDW and DEN:

    • Minneapolis St Paul Airport

    • St Louis Airport

    • Kansas City International Airport

How to find the cheapest flights from Chicago Midway Airport (MDW) to Denver International Airport (DEN)

  • $148 is currently the lowest price for a one-way Chicago Midway Airport to Denver International Airport flight. Return flights start from $295. These prices may change depending on demand.

  • Don't leave everything to the last moment. You're more likely to find cheap tickets from MDW to DEN if you book in advance. Airlines often offer some great early bird deals.

  • Schedule your trip for May. That's the cheapest month for flights from Chicago Midway Airport to Denver International Airport. If you're flexible with your dates, try out the 'Whole month' tool to see the lowest airfare across every month.

  • Finding cheap flights from MDW to DEN couldn't be easier with Price Alerts. All you need to do is create one of these automatic alerts and we'll get in touch when a new discounted fare appears.

  • Tailor your trip with filters. Pick your ideal arrival and departure times, airlines and total journey duration. You can also sort results by 'Fastest,' 'Best' or 'Cheapest' flights from Chicago Midway Airport to Denver International Airport.

Handy information about Chicago Midway Airport (MDW)

  • MDW's address is 5700 South Cicero.

  • 76% of flights taking off from Chicago Midway Airport make it to their destination on schedule.

  • Central Chicago to Chicago Midway Airport is around 16 kilometres. Depending on traffic, it'll take about 25 minutes to get there if you're ride-sharing, catching a taxi or driving.

  • You can expect a trip time of around 30 minutes on public transport.

  • Get your travels off to a stress-free start by staying near MDW. Whether you're catching an early flight from Chicago Midway Airport to Denver International Airport or just don't want to be rushed, these stays are perfect:

Arriving at Denver International Airport (DEN)

  • Hop off your Chicago Midway Airport to Denver International Airport flight and be snoozing in your hotel bed shortly after. If you're looking for a comfy option that's not too far from DEN, consider Baymont by Wyndham Denver International Airport.

  • Pick up a Denver International Airport rental car and explore Denver and beyond with your own set of wheels. Routes Car Rentals, Dollar and Budget are top providers you can book with here.

  • Booking your ride from Denver International Airport around one week in advance gives you the best chance of locking in a great deal.

Getting from Denver International Airport (DEN) to central Denver

  • DEN is located at 8500 Pena Boulevard.

  • Denver International Airport is approximately 40 kilometres from the centre of Denver. The drive time takes around 35 minutes.

  • Travelling on public transport will take you roughly 35 minutes.

When to fly to Denver International Airport (DEN)

  • It's time to work out your travel dates for your flight from Chicago Midway Airport to Denver International Airport. July is the busiest month to visit Denver. If you want a more relaxed vibe, go in January.

  • Book your flight from Chicago Midway Airport to Denver International Airport for July if you'd like to explore Denver during its warmest month. You can expect temperatures of between 14ºC (57ºF) and 32ºC (90ºF).

  • Look for cheap tickets from MDW to DEN in January if you want to travel in cooler conditions. Temperatures are at their lowest around then, ranging between -9ºC (16ºF) and 7ºC (45ºF) on average.

Explore more of the United States

  • Denver is easy to fall in love with, but there are so many other parts of the United States waiting to be discovered. About 105 kilometres south of Denver, a visit to Colorado Springs will keep you busy. Don't miss top attractions like Garden of the Gods, Pikes Peak Region Attractions and Red Rock Canyon.

  • If you're interested in discovering another great destination in the United States, consider Aurora, roughly 13 kilometres east of Denver. Plains Conservation Centre, DeLaney Homestead Historic District and Aircraft viewing are among its highlights.

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Prices shown on this page are estimated lowest prices only. Found in the last 12 days.