$82+ Cheap flights from Iowa to Chicago (CHI)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 6/2. Fares are subject to change and may not be available on all flights or dates of travel.
DSM — CHI
Jun 5 — Jun 121
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Iowa to Chicago with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Iowa to Chicago
Cheapest
Best
Last-minute
One-way
Cheapest flights from Iowa to ChicagoExplore the most affordable flight options available from Iowa to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 6, 2026.
Explore the most affordable flight options available from Iowa to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 6, 2026.
This Kiwi.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/238:25 pm
OMA
- ORD
1 stop24h 18m
Frontier
Tue 7/149:57 pm
ORD
- OMA
1 stop21h 23m
Frontier
Deal found 5/5![Frontier logo]()
$158
This Kiwi.com deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/128:05 pm
OMA
- ORD
1 stop24h 47m
Frontier
Tue 8/189:48 pm
ORD
- OMA
1 stop21h 46m
Frontier
Deal found 5/4![Frontier logo]()
$167
This Frontier deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/288:19 pm
OMA
- ORD
1 stop24h 13m
Frontier
Mon 6/19:37 pm
ORD
- OMA
1 stop21h 47m
Frontier
Deal found 5/3![Frontier logo]()
$181
This Kiwi.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/98:25 pm
OMA
- ORD
1 stop24h 18m
Frontier
Tue 6/169:48 pm
ORD
- OMA
1 stop21h 42m
Frontier
Deal found 5/5![Frontier logo]()
$191
This Kiwi.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/87:56 pm
OMA
- ORD
1 stop24h 47m
Frontier
Tue 6/169:48 pm
ORD
- OMA
1 stop21h 42m
Frontier
Deal found 5/5![Frontier logo]()
$193
This United Airlines deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/297:00 pm
MCW
- ORD
Nonstop1h 30m
United Airlines
Fri 6/57:35 am
ORD
- MCW
Nonstop1h 35m
United Airlines
Deal found 4/30![United Airlines logo]()
$202
This United Airlines deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/68:08 am
SUX
- ORD
Nonstop1h 52m
United Airlines
Sat 6/203:59 pm
ORD
- SUX
Nonstop1h 54m
United Airlines
Deal found 5/5![United Airlines logo]()
$204
This Kiwi.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/108:15 pm
OMA
- ORD
1 stop24h 28m
Frontier
Tue 6/169:48 pm
ORD
- OMA
1 stop21h 42m
Frontier
Deal found 5/5![Frontier logo]()
$213
This Kiwi.com deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/126:44 pm
DSM
- ORD
1 stop17h 40m
Multiple Airlines
Sat 6/138:00 pm
ORD
- DSM
1 stop26h 52m
Multiple Airlines
Deal found 5/2![Multiple Airlines logo]()
$223
This CheapOair deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/238:19 pm
OMA
- ORD
1 stop24h 13m
Frontier
Tue 5/269:37 pm
ORD
- OMA
1 stop21h 57m
Frontier
Deal found 5/4![Frontier logo]()
$225
This United Airlines deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/309:42 am
LSE
- ORD
Nonstop1h 24m
United Airlines
Thu 1/147:30 am
ORD
- LSE
Nonstop1h 26m
United Airlines
Deal found 4/30![United Airlines logo]()
$229
This Southwest deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/95:20 am
DSM
- MDW
Nonstop1h 20m
Southwest
Tue 6/169:20 pm
MDW
- DSM
Nonstop1h 25m
Southwest
Deal found 5/4![Southwest logo]()
$237
Best flights from Iowa to ChicagoDiscover carefully curated flight deals from Iowa to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 6, 2026.
Discover carefully curated flight deals from Iowa to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 6, 2026.
This United Airlines deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/269:45 am
MCW
- ORD
Nonstop1h 30m
United Airlines
Sun 6/287:35 am
ORD
- MCW
Nonstop1h 35m
United Airlines
Deal found 5/1![United Airlines logo]()
$202
This Kiwi.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/238:25 pm
OMA
- ORD
1 stop24h 18m
Frontier
Tue 7/211:50 pm
ORD
- OMA
2 stops29h 30m
Frontier
Deal found 5/5![Frontier logo]()
$214
This American Airlines deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/1811:52 am
LSE
- ORD
Nonstop1h 22m
American Airlines
Tue 6/2310:00 am
ORD
- LSE
Nonstop1h 22m
American Airlines
Deal found 5/4![American Airlines logo]()
$229
This Southwest deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/33:15 pm
DSM
- MDW
Nonstop1h 20m
Southwest
Thu 6/410:10 am
MDW
- DSM
Nonstop1h 20m
Southwest
Deal found 5/4![Southwest logo]()
$253
This Delta deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/176:03 pm
DSM
- ORD
1 stop3h 22m
Delta
Wed 6/2412:27 pm
ORD
- DSM
1 stop4h 27m
Delta
Deal found 5/1![Delta logo]()
$257
This United Airlines deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/109:45 am
MCW
- ORD
Nonstop1h 30m
United Airlines
Mon 6/154:47 pm
ORD
- MCW
Nonstop1h 38m
United Airlines
Deal found 5/1![United Airlines logo]()
$202
This Kiwi.com deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/47:07 pm
OMA
- RFD
1 stop25h 13m
Allegiant Air
Mon 6/87:53 pm
RFD
- OMA
1 stop15h 14m
Allegiant Air
Deal found 5/4![Allegiant Air logo]()
$421
This United Airlines deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/247:15 pm
MCW
- ORD
Nonstop1h 30m
United Airlines
Wed 7/294:47 pm
ORD
- MCW
Nonstop1h 38m
United Airlines
Deal found 5/5![United Airlines logo]()
$202
This American Airlines deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/125:25 pm
LSE
- ORD
Nonstop1h 35m
American Airlines
Mon 6/2211:00 pm
ORD
- LSE
Nonstop1h 19m
American Airlines
Deal found 5/3![American Airlines logo]()
$229
This Kiwi.com deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/228:19 pm
OMA
- RFD
2 stops36h 12m
Multiple Airlines
Mon 5/258:03 pm
RFD
- OMA
1 stop15h 19m
Multiple Airlines
Deal found 5/2![Multiple Airlines logo]()
$478
This American Airlines deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/165:25 pm
LSE
- ORD
Nonstop1h 35m
American Airlines
Thu 7/210:37 pm
ORD
- LSE
Nonstop1h 22m
American Airlines
Deal found 5/3![American Airlines logo]()
$229
This Delta deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/162:45 pm
DSM
- ORD
1 stop6h 40m
Delta
Tue 6/238:36 am
ORD
- DSM
1 stop5h 29m
Delta
Deal found 5/2![Delta logo]()
$257
This American Airlines deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/1111:52 am
LSE
- ORD
Nonstop1h 22m
American Airlines
Mon 6/1510:00 am
ORD
- LSE
Nonstop1h 22m
American Airlines
Deal found 5/3![American Airlines logo]()
$229
This Southwest deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/103:50 pm
DSM
- MDW
Nonstop1h 20m
Southwest
Wed 8/128:35 pm
MDW
- DSM
Nonstop1h 20m
Southwest
Deal found 5/3![Southwest logo]()
$283
This United Airlines deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/111:15 pm
MLI
- ORD
Nonstop1h 14m
United Airlines
Tue 6/2312:45 pm
ORD
- MLI
Nonstop1h 11m
United Airlines
Deal found 5/4![United Airlines logo]()
$239
This Delta deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/25:28 pm
DSM
- ORD
1 stop3h 52m
Delta
Thu 6/42:00 pm
ORD
- DSM
1 stop6h 36m
Delta
Deal found 5/3![Delta logo]()
$273
This American Airlines deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/2711:11 am
MLI
- ORD
Nonstop1h 11m
American Airlines
Sun 6/289:30 am
ORD
- MLI
Nonstop1h 11m
American Airlines
Deal found 5/3![American Airlines logo]()
$239
This United Airlines deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/147:00 pm
MCW
- ORD
Nonstop1h 25m
United Airlines
Sun 8/165:10 pm
ORD
- MCW
Nonstop1h 29m
United Airlines
Deal found 5/3![United Airlines logo]()
$242
This Southwest deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/33:35 pm
OMA
- MDW
Nonstop1h 25m
Southwest
Thu 6/48:40 am
MDW
- OMA
1 stop8h 05m
Southwest
Deal found 5/2![Southwest logo]()
$293
This Delta deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/3010:56 am
DSM
- ORD
1 stop5h 55m
Delta
Sat 6/61:44 pm
ORD
- DSM
1 stop6h 52m
Delta
Deal found 5/2![Delta logo]()
$289
This American Airlines deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/111:07 am
MLI
- ORD
Nonstop1h 15m
American Airlines
Mon 6/85:08 pm
ORD
- MLI
Nonstop1h 14m
American Airlines
Deal found 5/1![American Airlines logo]()
$239
This United Airlines deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/47:00 pm
MCW
- ORD
Nonstop1h 30m
United Airlines
Fri 6/267:35 am
ORD
- MCW
Nonstop1h 35m
United Airlines
Deal found 5/4![United Airlines logo]()
$242
This Southwest deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/512:30 pm
OMA
- MDW
Nonstop1h 20m
Southwest
Mon 9/75:40 am
MDW
- OMA
1 stop6h 50m
Southwest
Deal found 5/5![Southwest logo]()
$301
This United Airlines deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/117:00 pm
MCW
- ORD
Nonstop1h 25m
United Airlines
Mon 9/145:10 pm
ORD
- MCW
Nonstop1h 29m
United Airlines
Deal found 5/2![United Airlines logo]()
$242
This American Airlines deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/179:54 am
LSE
- ORD
Nonstop1h 25m
American Airlines
Sat 5/3010:45 pm
ORD
- LSE
Nonstop1h 21m
American Airlines
Deal found 5/3![American Airlines logo]()
$244
This Southwest deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/46:10 pm
OMA
- MDW
1 stop6h 00m
Southwest
Mon 6/89:25 pm
MDW
- OMA
Nonstop1h 30m
Southwest
Deal found 5/4![Southwest logo]()
$301
This Delta deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/106:00 am
DSM
- MDW
1 stop6h 39m
Delta
Wed 8/121:27 pm
MDW
- DSM
1 stop3h 44m
Delta
Deal found 5/3![Delta logo]()
$303
This United Airlines deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/17:00 pm
MCW
- ORD
Nonstop1h 30m
United Airlines
Mon 6/84:47 pm
ORD
- MCW
Nonstop1h 38m
United Airlines
Deal found 5/4![United Airlines logo]()
$242
This Kiwi.com deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/235:56 pm
OMA
- RFD
1 stop15h 36m
Allegiant Air
Mon 6/87:53 pm
RFD
- OMA
1 stop15h 14m
Allegiant Air
Deal found 5/2![Allegiant Air logo]()
$436
This Delta deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/11:25 pm
OMA
- ORD
1 stop5h 55m
Delta
Wed 6/38:42 am
ORD
- OMA
1 stop3h 43m
Delta
Deal found 5/3![Delta logo]()
$303
Last-minute flights from Iowa to ChicagoDiscover last-minute flight deals from Iowa to Chicago. Data last updated May 6, 2026 and is based on user searches.
Discover last-minute flight deals from Iowa to Chicago. Data last updated May 6, 2026 and is based on user searches.
This CheapOair deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/238:19 pm
OMA
- ORD
1 stop24h 13m
Frontier
Tue 5/269:37 pm
ORD
- OMA
1 stop21h 57m
Frontier
Deal found 5/4![Frontier logo]()
$225
This Frontier deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/288:19 pm
OMA
- ORD
1 stop24h 13m
Frontier
Mon 6/19:37 pm
ORD
- OMA
1 stop21h 47m
Frontier
Deal found 5/3![Frontier logo]()
$181
This United Airlines deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/68:08 am
SUX
- ORD
Nonstop1h 52m
United Airlines
Sat 6/203:59 pm
ORD
- SUX
Nonstop1h 54m
United Airlines
Deal found 5/5![United Airlines logo]()
$204
This Kiwi.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/87:56 pm
OMA
- ORD
1 stop24h 47m
Frontier
Tue 6/169:48 pm
ORD
- OMA
1 stop21h 42m
Frontier
Deal found 5/5![Frontier logo]()
$193
This Kiwi.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/98:25 pm
OMA
- ORD
1 stop24h 18m
Frontier
Tue 6/169:48 pm
ORD
- OMA
1 stop21h 42m
Frontier
Deal found 5/5![Frontier logo]()
$191
This Southwest deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/95:20 am
DSM
- MDW
Nonstop1h 20m
Southwest
Tue 6/169:20 pm
MDW
- DSM
Nonstop1h 25m
Southwest
Deal found 5/4![Southwest logo]()
$237
This United Airlines deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/96:00 am
DSM
- ORD
Nonstop1h 37m
United Airlines
Tue 6/169:20 pm
ORD
- DSM
Nonstop1h 31m
United Airlines
Deal found 5/4![United Airlines logo]()
$237
This Kiwi.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/108:15 pm
OMA
- ORD
1 stop24h 28m
Frontier
Tue 6/169:48 pm
ORD
- OMA
1 stop21h 42m
Frontier
Deal found 5/5![Frontier logo]()
$213
This American Airlines deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/1111:52 am
LSE
- ORD
Nonstop1h 22m
American Airlines
Thu 6/1811:00 pm
ORD
- LSE
Nonstop1h 19m
American Airlines
Deal found 5/2![American Airlines logo]()
$229
This Kiwi.com deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/126:44 pm
DSM
- ORD
1 stop17h 40m
Multiple Airlines
Sat 6/138:00 pm
ORD
- DSM
1 stop26h 52m
Multiple Airlines
Deal found 5/2![Multiple Airlines logo]()
$223
This American Airlines deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/171:51 pm
DSM
- ORD
Nonstop1h 42m
American Airlines
Wed 6/245:00 pm
ORD
- DSM
Nonstop1h 39m
American Airlines
Deal found 5/3![American Airlines logo]()
$238
This Kiwi.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/238:25 pm
OMA
- ORD
1 stop24h 18m
Frontier
Tue 7/149:57 pm
ORD
- OMA
1 stop21h 23m
Frontier
Deal found 5/5![Frontier logo]()
$158
One-way flights from Iowa to ChicagoSearch for one-way flight options from Iowa to Chicago. Find affordable one-way fares based on user searches. Data last updated May 6, 2026.
Search for one-way flight options from Iowa to Chicago. Find affordable one-way fares based on user searches. Data last updated May 6, 2026.
This Kiwi.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/28:19 pm
OMA
- ORD
1 stop24h 13m
Frontier
Deal found 5/5![Frontier logo]()
$82
This Frontier deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/12:16 pm
DSM
- ORD
1 stop6h 16m
Frontier
Deal found 5/4![Frontier logo]()
$90
This Expedia deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/172:16 pm
DSM
- ORD
1 stop6h 27m
Frontier
Deal found 5/5![Frontier logo]()
$95
This Kiwi.com deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/35:55 pm
CID
- ORD
1 stop18h 29m
Multiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$109
This Kiwi.com deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/108:15 pm
OMA
- ORD
1 stop24h 28m
Frontier
Deal found 5/4![Frontier logo]()
$109
This Kiwi.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/68:19 pm
OMA
- ORD
1 stop24h 13m
Frontier
Deal found 5/5![Frontier logo]()
$111
This Kiwi.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/16:11 pm
CID
- ORD
2 stops37h 44m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$112
This Frontier deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/262:16 pm
DSM
- ORD
1 stop6h 27m
Frontier
Deal found 5/5![Frontier logo]()
$115
This Kiwi.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/284:01 pm
DSM
- ORD
2 stops40h 02m
Multiple Airlines
Deal found 5/5![Multiple Airlines logo]()
$116
This Kiwi.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/28:19 pm
OMA
- MDW
2 stops14h 50m
Frontier
Deal found 5/5![Frontier logo]()
$116
This Kiwi.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/268:19 pm
OMA
- MDW
2 stops14h 50m
Frontier
Deal found 5/5![Frontier logo]()
$118
This Southwest deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/175:20 am
DSM
- MDW
Nonstop1h 20m
Southwest
Deal found 4/30![Southwest logo]()
$119
Find flight deals from Iowa to Chicago
Keep the following information in mind while searching for Iowa to Chicago flight deals. Data was last updated May 6, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $158 (Kiwi.com) |
One-way from | $82 (Kiwi.com) |
Popular in | April |
Cheapest in | September |
Average price | $257 |
Good round-trip deal | $218 or less |
Good one-way deal | $42 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Iowa to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated May 6, 2026.
Use the filters below to find and compare flights from Iowa to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Mason CityChicago
MCW - ORD
MCWORD
Mason City
Fri 6/26
9:45 am-11:15 am
Nonstop1h 30m
Chicago O'Hare Intl
Sun 6/28
7:35 am-9:10 am
Nonstop1h 35m
$202
Mason CityChicago
MCW - ORD
MCWORD
Mason City
Wed 6/10
9:45 am-11:15 am
Nonstop1h 30m
Chicago O'Hare Intl
Mon 6/15
4:47 pm-6:25 pm
Nonstop1h 38m
$202
Mason CityChicago
MCW - ORD
MCWORD
Mason City
Fri 7/24
7:15 pm-8:45 pm
Nonstop1h 30m
Chicago O'Hare Intl
Wed 7/29
4:47 pm-6:25 pm
Nonstop1h 38m
$202
OmahaChicago
OMA - ORD
OMAORD
Omaha Eppley Airfield
Tue 6/23
8:25 pm-8:43 pm
1 stop24h 18m
Chicago O'Hare Intl
Tue 7/21
1:50 pm-7:20 pm
2 stops29h 30m
$214
La CrosseChicago
LSE - ORD
LSEORD
La Crosse
Thu 6/18
11:52 am-1:14 pm
Nonstop1h 22m
Chicago O'Hare Intl
Tue 6/23
10:00 am-11:22 am
Nonstop1h 22m
$229
La CrosseChicago
LSE - ORD
LSEORD
La Crosse
Fri 6/12
5:25 pm-7:00 pm
Nonstop1h 35m
Chicago O'Hare Intl
Mon 6/22
11:00 pm-12:19 am
Nonstop1h 19m
$229
La CrosseChicago
LSE - ORD
LSEORD
La Crosse
Tue 6/16
5:25 pm-7:00 pm
Nonstop1h 35m
Chicago O'Hare Intl
Thu 7/2
10:37 pm-11:59 pm
Nonstop1h 22m
$229
La CrosseChicago
LSE - ORD
LSEORD
La Crosse
Thu 6/11
11:52 am-1:14 pm
Nonstop1h 22m
Chicago O'Hare Intl
Mon 6/15
10:00 am-11:22 am
Nonstop1h 22m
$229
MolineChicago
MLI - ORD
MLIORD
Moline Quad-City
Thu 6/11
1:15 pm-2:29 pm
Nonstop1h 14m
Chicago O'Hare Intl
Tue 6/23
12:45 pm-1:56 pm
Nonstop1h 11m
$239
Quickest round-trip
MolineChicago
MLI - ORD
MLIORD
Moline Quad-City
Sat 6/27
11:11 am-12:22 pm
Nonstop1h 11m
Chicago O'Hare Intl
Sun 6/28
9:30 am-10:41 am
Nonstop1h 11m
$239
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Iowa to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Iowa with our price prediction graph.
OMA-ORD
MCW-ORD
SUX-ORD
DSM-ORD
LSE-ORD
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Iowa to Chicago
USIA-CHI
OMA-ORD
MCW-ORD
SUX-ORD
DSM-ORD
How far ahead should I book a flight from Iowa to Chicago?
To ensure you get the cheapest price possible for a flight from Iowa to Chicago, you should look to book at least 84 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.
What is the cheapest month to book a flight from Iowa to Chicago?
Currently, February is the cheapest month in which you can book a flight from Iowa to Chicago (average of $126). Flying from Iowa to Chicago in January is currently the most expensive (average of $179). 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.
What is the cheapest time of day to fly from IA to CHI?
Find hourly flight availability from Iowa to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 6, 2026.
Unlike in the evening, when flights are generally more expensive, you can save up to 28% on flights from Iowa to Chicago by exploring options for tickets in the morning.
What is the cheapest day to fly from Iowa to Chicago?
Use this chart to determine the cheapest time to fly round-trip from Iowa to Chicago. Price data was last updated on May 2, 2026.
Travelers seeking maximum savings on their Iowa to Chicago flight should consider departing on Thursday at noon when fares are most often at their lowest. Sunday evenings flights should be avoided if possible as fares are typically the most expensive at this time.
Weekly flight availability from Iowa to Chicago
Explore weekly flight availability from Iowa to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated May 6, 2026.
The most flights from USIA to CHI are scheduled on a Tuesday (60 on average). You will have fewer flight options on Friday, which is when the least amount of flights are scheduled (39 on average).
How much does it cost to fly round-trip from Iowa to Chicago?
Related info for your journey
Find useful and relevant information for your journey from Iowa to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Hammond
Porter
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Chicago flight routes
Complete your trip
Flights by cabin class
Other flight options
Popular flights
Top destinations
Alternative routes for Iowa to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on May 6, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Iowa to Chicago by cabin class
Find flights from Iowa to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Iowa and Chicago flights
Browse other Iowa and Chicago flight options. Last updated on May 6, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Iowa to Chicago flights
Consider these flights traveling from Iowa to Chicago.
Top 4 airlines flying from Iowa to Chicago
Discover the top 4 airlines that operate flights from Iowa to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated May 6, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$59 | Average$91 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$148 | Average$244 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$168 | Average$222 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$179 | Average$275 | FlexibilityNo cancel fee | On-time69% |