
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $151 (American Airlines) |
One-way from | $66 (Southwest) |
Popular in | January |
Cheapest in | September |
Average price | $260 |
Good round-trip deal | $392 or less |
Good one-way deal | $188 or less |
Fly from
Fly to
Route
Depart
Return
Price
Des MoinesChicago
DSM - MDW
DSMMDW
Des Moines
Tue 4/14
3:15 pm-4:35 pm
Nonstop1h 20m
Chicago Midway
Thu 4/16
9:45 pm-11:05 pm
Nonstop1h 20m
Des MoinesChicago
DSM - MDW
DSMMDW
Des Moines
Wed 4/1
6:55 am-1:25 pm
1 stop6h 30m
Chicago Midway
Sat 4/4
1:10 pm-4:54 pm
1 stop3h 44m
Des MoinesChicago
DSM - ORD
DSMORD
Des Moines
Wed 4/1
6:55 am-11:35 am
1 stop4h 40m
Chicago O'Hare Intl
Sat 4/4
9:50 am-4:54 pm
1 stop7h 04m
Des MoinesChicago
DSM - ORD
DSMORD
Des Moines
Tue 5/19
2:39 pm-7:20 pm
1 stop4h 41m
Chicago O'Hare Intl
Wed 5/20
2:00 pm-8:36 pm
1 stop6h 36m
Des MoinesChicago
DSM - ORD
DSMORD
Des Moines
Tue 5/19
6:15 am-7:53 am
Nonstop1h 38m
Chicago O'Hare Intl
Fri 5/22
7:40 pm-9:12 pm
Nonstop1h 32m
Des MoinesChicago
DSM - ORD
DSMORD
Des Moines
Sat 3/21
6:00 am-7:45 am
Nonstop1h 45m
Chicago O'Hare Intl
Sat 3/28
10:18 pm-11:40 pm
Nonstop1h 22m
Des MoinesChicago
DSM - ORD
DSMORD
Des Moines
Thu 3/19
10:04 am-11:37 am
Nonstop1h 33m
Chicago O'Hare Intl
Thu 3/26
7:30 am-8:54 am
Nonstop1h 24m
Des MoinesChicago
DSM - MDW
DSMMDW
Des Moines
Fri 4/17
6:10 am-12:43 pm
1 stop6h 33m
Chicago Midway
Mon 4/20
2:12 pm-9:08 pm
1 stop6h 56m
Des MoinesChicago
DSM - ORD
DSMORD
Des Moines
Fri 3/27
6:49 pm-8:25 pm
Nonstop1h 36m
Chicago O'Hare Intl
Sun 3/29
7:55 pm-9:27 pm
Nonstop1h 32m
Des MoinesChicago
DSM - ORD
DSMORD
Des Moines
Fri 4/3
3:21 pm-4:57 pm
Nonstop1h 36m
Chicago O'Hare Intl
Sun 4/5
9:22 pm-10:59 pm
Nonstop1h 37m
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
Booking 41 days in advance of your planned departure date is, on average, the best time to get cheap flights from Des Moines to Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
Currently, February is the cheapest month in which you can book a flight from Des Moines to Chicago (average of $148). Flying from Des Moines to Chicago in January is currently the most expensive (average of $189). 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 in the afternoon, when flights are generally more expensive, you can save up to 29% on flights from Des Moines to Chicago by exploring options for tickets in the morning.
Travelers seeking maximum savings on their Des Moines to Chicago flight should consider departing on Wednesday afternoons when fares are most often at their lowest. Tuesday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
The most flights from DSM to CHI are scheduled on a Thursday (37 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (20 on average).
Comfort
Entertainment
Overall
Boarding
Crew
Food
Reviews
Thomas,Dec 2025
SEA - DEN
Comfort
Entertainment
Overall
Boarding
Crew
Food
Reviews
Thomas,Dec 2025
SEA - DEN
Comfort
Entertainment
Overall
Boarding
Crew
Food
Reviews
Thomas,Dec 2025
SEA - DEN
Comfort
Entertainment
Overall
Boarding
Crew
Food
Reviews
Thomas,Dec 2025
SEA - DEN
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$148 | Average$228 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$189 | Average$253 | FlexibilityNo cancel fee | On-time69% |