
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $181 (Frontier) |
One-way from | $85 (Kiwi.com) |
Popular in | March |
Cheapest in | August |
Average price | $266 |
Good round-trip deal | $294 or less |
Good one-way deal | $162 or less |
Fly from
Fly to
Route
Depart
Return
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Wed 6/10
10:15 am-4:50 pm
1 stop5h 35m
Chicago Midway
Tue 6/16
7:00 am-8:35 am
Nonstop2h 35m
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Wed 7/1
6:00 am-1:09 pm
1 stop6h 09m
Chicago Midway
Tue 7/7
5:10 pm-12:23 am
1 stop8h 13m
DenverChicago
DEN - ORD
DENORD
Denver Intl
Thu 6/4
6:00 am-9:38 am
Nonstop2h 38m
Chicago O'Hare Intl
Mon 6/8
5:00 am-6:42 am
Nonstop2h 42m
DenverChicago
DEN - ORD
DENORD
Denver Intl
Tue 6/9
7:40 am-11:23 am
Nonstop2h 43m
Chicago O'Hare Intl
Sun 6/14
5:00 am-6:42 am
Nonstop2h 42m
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Tue 6/9
6:15 am-9:40 am
Nonstop2h 25m
Chicago Midway
Fri 6/12
9:25 pm-11:05 pm
Nonstop2h 40m
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Wed 7/1
12:15 pm-5:00 pm
1 stop3h 45m
Chicago Midway
Sat 7/4
7:35 am-9:15 am
Nonstop2h 40m
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Sat 6/27
12:05 pm-5:00 pm
1 stop3h 55m
Chicago Midway
Tue 6/30
9:05 pm-10:50 pm
Nonstop2h 45m
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Mon 6/8
5:55 am-9:20 am
Nonstop2h 25m
Chicago Midway
Mon 6/15
5:15 am-6:50 am
Nonstop2h 35m
DenverChicago
DEN - ORD
DENORD
Denver Intl
Fri 7/3
6:00 am-11:31 am
1 stop4h 31m
Chicago O'Hare Intl
Wed 7/8
5:54 pm-11:27 pm
1 stop6h 33m
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Fri 7/31
3:10 pm-10:15 pm
1 stop6h 05m
Chicago Midway
Tue 8/4
7:25 pm-11:34 pm
1 stop5h 09m
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*1 star | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars |
The price you pay for your flight from Denver to Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 78 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
Currently, August is the cheapest month in which you can book a flight from Denver to Chicago (average of $220). Flying from Denver to Chicago in December is currently the most expensive (average of $533). 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.
It’s optimal to fly from Denver to Chicago in the evening. By choosing this option you can save up to 49% on the cost of your flight, compared to a flight at noon.
Travelers seeking maximum savings on their Denver to Chicago flight should consider departing on Saturday afternoons 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.
The most flights from DEN to CHI are scheduled on a Sunday (79 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (60 on average).
Entertainment
Crew
Boarding
Overall
Comfort
Food
Reviews
Dominic,Mar 2026
MCO - SMF
Entertainment
Crew
Boarding
Overall
Comfort
Food
Reviews
Dominic,Mar 2026
MCO - SMF
Entertainment
Crew
Boarding
Overall
Comfort
Food
Reviews
Dominic,Mar 2026
MCO - SMF
Entertainment
Crew
Boarding
Overall
Comfort
Food
Reviews
Dominic,Mar 2026
MCO - SMF
Entertainment
Crew
Boarding
Overall
Comfort
Food
Reviews
Dominic,Mar 2026
MCO - SMF
Entertainment
Crew
Boarding
Overall
Comfort
Food
Reviews
Dominic,Mar 2026
MCO - SMF
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$75 | Average$186 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$126 | Average$191 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$157 | Average$278 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$159 | Average$261 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$168 | Average$336 | FlexibilityNo cancel fee | On-time69% |