Southwest offers free snacks and non-alcoholic beverages, enhancing the in-flight experience.
Southwest’s Rapid Rewards program offers points for flights, with no blackout dates for redemption.

Most accurate provider | Justfly.com 3 stars |
|---|---|
Most trusted provider | Justfly.com 3 stars |
Round-trip from | $112 (Frontier) |
One-way from | $63 (Super.com) |
Popular in | December |
Cheapest in | February |
Average price | $226 |
Good round-trip deal | $154 or less |
Good one-way deal | $96 or less |
Fly from
Fly to
Route
Depart
Return
Price
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Thu 1/8
6:25 pm-9:50 pm
Nonstop2h 25m
Chicago Midway
Mon 1/12
7:55 pm-9:40 pm
Nonstop2h 45m
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Wed 1/14
9:45 am-1:10 pm
Nonstop2h 25m
Chicago Midway
Fri 1/16
8:50 pm-10:35 pm
Nonstop2h 45m
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Wed 12/3
8:00 am-11:25 am
Nonstop2h 25m
Chicago Midway
Tue 12/9
9:40 am-11:20 am
Nonstop2h 40m
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Tue 2/10
11:20 am-6:35 pm
1 stop6h 15m
Chicago Midway
Sun 2/15
5:40 am-7:30 am
Nonstop2h 50m
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Tue 12/9
8:05 am-12:35 pm
1 stop3h 30m
Chicago Midway
Tue 12/16
8:10 am-12:10 pm
1 stop5h 00m
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Sat 12/6
1:25 pm-4:45 pm
Nonstop2h 20m
Chicago Midway
Mon 12/8
9:40 am-11:20 am
Nonstop2h 40m
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Tue 12/9
8:05 am-12:35 pm
1 stop3h 30m
Chicago Midway
Thu 12/11
9:50 am-2:25 pm
1 stop5h 35m
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Sat 1/10
1:10 pm-6:30 pm
1 stop4h 20m
Chicago Midway
Sun 1/11
8:50 pm-10:35 pm
Nonstop2h 45m
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Sat 12/13
5:45 am-11:45 am
1 stop5h 00m
Chicago Midway
Thu 12/18
9:40 pm-11:15 pm
Nonstop2h 35m
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Tue 12/16
8:05 am-12:35 pm
1 stop3h 30m
Chicago Midway
Fri 12/19
12:55 pm-2:35 pm
Nonstop2h 40m
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*2 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star |
To ensure you get the cheapest price possible for a flight from Denver to Chicago Midway Airport, you should look to book at least 75 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
Currently, January is the cheapest month in which you can book a flight from Denver to Chicago Midway Airport (average of $58). Flying from Denver to Chicago Midway Airport in October is currently the most expensive (average of $156). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
Unlike at noon, when flights are generally more expensive, you can save up to 44% on flights from Denver to Chicago Midway Airport by exploring options for tickets in the evening.
Travelers seeking maximum savings on their Denver to Chicago Midway Airport flight should consider departing on Tuesday evenings when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Comfort
Overall
Crew
Boarding
Food
Entertainment
Reviews
Mike,Aug 2025
OKC - AUS
Comfort
Overall
Crew
Boarding
Food
Entertainment
Reviews
Mike,Aug 2025
OKC - AUS
Comfort
Overall
Crew
Boarding
Food
Entertainment
Reviews
Mike,Aug 2025
OKC - AUS
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$68 | Average$173 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$158 | Average$259 | FlexibilityNo cancel fee | On-time63% |