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Cheap flight tickets from Denver to Chicago Midway

Compare Denver to Chicago Midway flight deals

Find the cheapest month or even day of the year to fly to Chicago Midway

Book the best Chicago Midway fare with no extra fees

Flight deals from Denver to Chicago Midway Airport

Looking for a cheap last-minute deal or the best return flight from Denver to Chicago Midway Airport? If you want to travel next month, return fares start from RM705. Find the lowest prices on one-way and return tickets right here.
Chicago.RM708 per passenger.Departing Tue, 5 May, returning Wed, 6 May.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Denver International on Tue, 5 May, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Wed, 6 May, arriving in Denver International.Price includes taxes and charges.From RM708, select.
Chicago.RM708 per passenger.Departing Sat, 18 Apr, returning Tue, 21 Apr.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Denver International on Sat, 18 Apr, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Tue, 21 Apr, arriving in Denver International.Price includes taxes and charges.From RM708, select.
Chicago.RM711 per passenger.Departing Mon, 27 Apr, returning Fri, 1 May.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Denver International on Mon, 27 Apr, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Fri, 1 May, arriving in Denver International.Price includes taxes and charges.From RM711, select.
Chicago.RM790 per passenger.Departing Sat, 30 May, returning Wed, 3 Jun.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Denver International on Sat, 30 May, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Wed, 3 Jun, arriving in Denver International.Price includes taxes and charges.From RM790, select.
Chicago.RM790 per passenger.Departing Tue, 5 May, returning Tue, 5 May.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Denver International on Tue, 5 May, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 5 May, arriving in Denver International.Price includes taxes and charges.From RM790, select.
Chicago.RM790 per passenger.Departing Tue, 21 Apr, returning Tue, 28 Apr.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Denver International on Tue, 21 Apr, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 28 Apr, arriving in Denver International.Price includes taxes and charges.From RM790, select.
Chicago.RM791 per passenger.Departing Wed, 3 Jun, returning Wed, 10 Jun.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Denver International on Wed, 3 Jun, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 10 Jun, arriving in Denver International.Price includes taxes and charges.From RM791, select.
Chicago.RM832 per passenger.Departing Thu, 28 May, returning Tue, 2 Jun.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Denver International on Thu, 28 May, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 2 Jun, arriving in Denver International.Price includes taxes and charges.From RM832, select.
Chicago.RM848 per passenger.Departing Sat, 11 Jul, returning Wed, 15 Jul.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Denver International on Sat, 11 Jul, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 15 Jul, arriving in Denver International.Price includes taxes and charges.From RM848, select.
Chicago.RM860 per passenger.Departing Sat, 18 Apr, returning Mon, 4 May.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Denver International on Sat, 18 Apr, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Mon, 4 May, arriving in Denver International.Price includes taxes and charges.From RM860, select.
Chicago.RM906 per passenger.Departing Fri, 31 Jul, returning Sat, 1 Aug.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Denver International on Fri, 31 Jul, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Sat, 1 Aug, arriving in Denver International.Price includes taxes and charges.From RM906, select.
Chicago.RM948 per passenger.Departing Mon, 30 Mar, returning Mon, 6 Apr.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Denver International on Mon, 30 Mar, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Mon, 6 Apr, arriving in Denver International.Price includes taxes and charges.From RM948, select.
Chicago.RM965 per passenger.Departing Thu, 25 Jun, returning Thu, 2 Jul.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Denver International on Thu, 25 Jun, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Thu, 2 Jul, arriving in Denver International.Price includes taxes and charges.From RM965, select.
Chicago.RM1,006 per passenger.Departing Fri, 3 Jul, returning Sat, 1 Aug.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Denver International on Fri, 3 Jul, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 1 Aug, arriving in Denver International.Price includes taxes and charges.From RM1,006, select.
Chicago.RM1,020 per passenger.Departing Sat, 12 Sep, returning Mon, 14 Sep.Return flight with Delta.Outbound indirect flight with Delta, departs from Denver International on Sat, 12 Sep, arriving in Chicago Midway.Inbound indirect flight with Delta, departs from Chicago Midway on Mon, 14 Sep, arriving in Denver International.Price includes taxes and charges.From RM1,020, select.
Chicago.RM1,028 per passenger.Departing Wed, 25 Mar, returning Sat, 28 Mar.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Denver International on Wed, 25 Mar, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Sat, 28 Mar, arriving in Denver International.Price includes taxes and charges.From RM1,028, select.

Find the cheapest month to fly from Denver to Chicago Midway

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Denver to Chicago Midway flights are currently cheapest in April.
Mar
from RM1,024
Apr
from RM705
May
from RM705
Jun
from RM788
Jul
from RM844
Aug
from RM1,035
Sep
from RM1,016
Oct
Find prices
Nov
from RM1,457
Dec
from RM1,296
Jan
Find prices
Feb
Find prices

Direct flights from Denver to Chicago Midway

Denver to Chicago Midway: Alternative routes

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

Chicago Midway

14km from central Chicago
Closest
from RM705
Search flights

Chicago O'Hare International

25km from central Chicago
Cheapest
from RM360
Search flights

Chicago Dupage County

51km from central Chicago
Search flights

Chicago Rockford

126km from central Chicago
from RM2,090
Search flights

Denver to Chicago: Flight information

The things to know before you go.
Cheapest flight foundRM705
Cheapest month to flyApril
Average flight time2 hrs, 23 mins
Most popular airlineSouthwest Airlines
Average flights per week48

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

The best price we found for a return flight from Denver to Chicago Midway is RM705. 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 23 minutes is the average flight time from Denver to Chicago Midway.
Southwest Airlines and United fly direct from Denver to Chicago Midway.
As of March 2026, there are 144 flights per week flying from Denver to Chicago Midway.
The cheapest month to fly from Denver to Chicago Midway is usually April.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Denver to Chicago Midway Airport on Saturday, 18 April 2026.
Yes – the average flight time is 2 hours and 23 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 Chicago Midway 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 Chicago is around 40 days in advance, so don’t leave your flight to the last minute.

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

  • Your travels get underway at Denver's main airport, Denver International Airport (DEN). Explore the options for reserving a flight from Denver to Chicago Midway International Airport (MDW) departing from this terminal.

  • Expect to be travelling for 2 hours 20 minutes. On average, that's the duration of a direct Denver to Chicago Midway International Airport flight.

  • The timezone in Chicago is UTC-5, which is one hour ahead of Denver. Chicago Midway International Airport is located in Chicago.

  • Denver International Airport (DEN) to Chicago Midway International Airport (MDW) is the most popular route. There are 32 direct weekly departures to pick from. If you prefer starting your day later, take the last flight with Southwest Airlines at 9:55pm. Opt for the first DEN to MDW departure operated by Southwest Airlines at 5am if you'd rather get going earlier.

  • To ensure you catch your flight from Denver to MDW, leave enough time to navigate the airport and find your gate. Turning up two hours before international departures and one hour before domestic flights is the general travel rule.

  • In high season, expect extended wait times and show up earlier. Aim for at least two hours ahead for domestic flights and up to four hours for international trips.

Airports in Denver

Denver International Airport (DEN)

  • Enjoy an uninterrupted journey from Denver International Airport (DEN). Nonstop flights from Denver to Chicago Midway International Airport (MDW) are available from here.

  • Southwest Airlines is a leading airline that operates direct flights from Denver to Chicago Midway International Airport jetting out of DEN.

  • The preferred airline for passengers flying between DEN and MDW is Southwest Airlines.

  • With a reliable 81.77% of services arriving as planned, Southwest Airlines is the most punctual carrier operating on this route.

  • Located around 40 kilometres from the centre of Denver, DEN can be reached in about 35 minutes by car, depending on traffic. The journey on public transport will take roughly 1 hour 30 minutes.

  • Need a convenient place to stay before your flight from Denver to Chicago Midway International Airport? Consider Baymont by Wyndham Denver International Airport. Enjoy a good night's sleep here before making your way to Denver International Airport.

  • Denver International Airport scores high marks for its on-time performance. 80.23% of flights that depart DEN reach their destination on time.

  • The address for DEN is 8500 Pena Boulevard.

About Chicago Midway International Airport (MDW)

  • If you have a late flight from Denver to Chicago Midway International Airport, few things beat the convenience of staying close to the terminal. Grab your luggage from the carousel and then be showered and relaxing soon after at one of these options near MDW:

  • Grab a Chicago Midway International Airport rental car and discover Chicago and beyond with your own set of wheels. Dollar, Hertz and Budget are well-known companies you can book with here.

  • Booking your vehicle around four weeks ahead of your Denver to Chicago Midway International Airport flight can help you lock in a great deal.

  • The address for MDW is 5700 South Cicero.

Getting from Chicago Midway International Airport (MDW) to central Chicago

  • The centre of Chicago is roughly 14 kilometres from Chicago Midway International Airport. Journey times by car hire or cab will vary based on time of day, so do some research before you go.

  • When travelling by public transport, expect a journey time of about 45 minutes.

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

  • RM351 is currently the best price for a one-way ticket from Denver to Chicago Midway International Airport. Return flights start from RM705. These prices can change based on demand and availability.

  • Don't leave everything to the last moment. You're more likely to find cheap flights from Denver to MDW if you book ahead. Airlines often have some excellent early bird discounts.

  • If you can be flexible with your trip dates, use the 'Whole month' tool. It'll show you the cheapest price across every month when searching for your Denver to Chicago Midway International Airport ticket.

  • Be the first to know about deals for plane tickets from Denver to MDW by setting up a Price Alert. We'll send you an email or notification on the app when fares go down.

  • Lock in a cheap flight from Denver to Chicago Midway International Airport by using the search filters. Select your ideal times, number of stops and airlines, then sort the results by 'Cheapest' for the best deals.

The best time to fly from Denver to Chicago Midway International Airport (MDW)

  • July is the most popular month for flights from Denver to Chicago Midway International Airport (MDW). Plan your visit to Chicago in May for a more laid-back experience.

  • When booking your Denver to MDW plane ticket, consider what kind of weather works for you. July is the warmest month in Chicago, with temperatures ranging from 15ºC (59ºF) to 29ºC (84ºF).

  • January sees temperatures of between -12ºC (10ºF) and 3ºC (37ºF). Look for cheap tickets from Denver to Chicago Midway International Airport around that time if you'd rather travel in cooler conditions.

More about Chicago

  • Start your Chicago trip off on the right foot by choosing the perfect place to stay. Once you've booked your flight from Denver to Chicago Midway International Airport, explore our selection of hotels including:

  • There are so many things to see and do in this city, it can be difficult to know where to start. Millennium Park, Lollapalooza and Art Institute of Chicago are top attractions which should be on any good Chicago itinerary.

Explore more of the United States

  • Chicago is easy to fall in love with, but there are so many other parts of the United States just waiting to be explored. Around 257 kilometres south-east of Chicago, a visit to Indianapolis will keep you busy. Start with popular sights like 9-11 Memorial, Lucas Oil Stadium and Eiteljorg Museum.

  • Milwaukee is another standout destination in the United States and is around 137 kilometres north of Chicago. No journey is complete without a visit to Richards Duplex Apartments by Frank Lloyd Wright, Miller Park and Milwaukee County Zoo.

Plan the rest of your trip from Denver to Chicago

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.