$90+ Cheap flights from Wyoming 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 5/17. Fares are subject to change and may not be available on all flights or dates of travel.
JAC — CHI
Apr 23 — Apr 301
Round-trip
1 adult, Economy
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Cheapest flights from Wyoming to ChicagoExplore the most affordable flight options available from Wyoming to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on März 24, 2026.
Explore the most affordable flight options available from Wyoming to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on März 24, 2026.
This United Airlines deal was found by Cheapflights users on 3/24. 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.
Di 5/58:20 pm
DEN
- ORD
Nonstop2h 37m
United Airlines
Sa 5/98:20 pm
ORD
- DEN
Nonstop2h 59m
United Airlines
Deal found 3/24![United Airlines logo]()
$175
This Southwest deal was found by Cheapflights users on 3/23. 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.
Do 4/168:20 pm
DEN
- MDW
Nonstop2h 20m
Southwest
Di 4/2112:35 pm
MDW
- DEN
Nonstop2h 35m
Southwest
Deal found 3/23![Southwest logo]()
$175
This Cheapflightsfares deal was found by Cheapflights users on 3/23. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Do 6/44:59 pm
DEN
- ORD
Nonstop2h 38m
Frontier
So 6/79:42 pm
ORD
- DEN
Nonstop3h 10m
Frontier
Deal found 3/23![Frontier logo]()
$176
This Southwest deal was found by Cheapflights users on 3/23. 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.
Sa 5/96:30 am
DEN
- MDW
Nonstop2h 20m
Southwest
Mi 5/138:50 pm
MDW
- DEN
Nonstop2h 45m
Southwest
Deal found 3/23![Southwest logo]()
$176
This Super.com deal was found by Cheapflights users on 3/22. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sa 4/119:00 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Mo 4/132:29 pm
ORD
- DEN
Nonstop3h 11m
Frontier
Deal found 3/22![Frontier logo]()
$177
This Kiwi.com deal was found by Cheapflights users on 3/19. 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.
Fr 4/243:45 pm
DEN
- ORD
1 stop6h 37m
Frontier
Mo 4/278:58 pm
ORD
- DEN
1 stop8h 01m
Frontier
Deal found 3/19![Frontier logo]()
$178
This Lucky2Go deal was found by Cheapflights users on 3/21. 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 Lucky2Go is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Di 5/55:00 pm
DEN
- MDW
1 stop20h 12m
Frontier
Di 5/123:07 pm
MDW
- DEN
1 stop16h 26m
Frontier
Deal found 3/21![Frontier logo]()
$178
This Cheapflightsfares deal was found by Cheapflights users on 3/23. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fr 4/1711:59 pm
DEN
- ORD
1 stop9h 38m
Frontier
So 4/195:59 am
ORD
- DEN
1 stop7h 10m
Frontier
Deal found 3/23![Frontier logo]()
$179
This Frontier deal was found by Cheapflights users on 3/21. 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.
Mi 5/65:05 am
DEN
- MDW
1 stop8h 07m
Frontier
Mi 5/1312:04 pm
MDW
- DEN
1 stop11h 20m
Frontier
Deal found 3/21![Frontier logo]()
$179
This Expedia deal was found by Cheapflights users on 3/20. 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.
Do 4/236:30 am
DEN
- MDW
1 stop7h 34m
Frontier
Sa 4/256:00 am
MDW
- DEN
1 stop7h 14m
Frontier
Deal found 3/20![Frontier logo]()
$180
This Frontier deal was found by Cheapflights users on 3/23. 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.
Mi 4/84:34 pm
DEN
- ORD
1 stop6h 06m
Frontier
Di 4/2110:45 am
ORD
- DEN
1 stop12h 44m
Frontier
Deal found 3/23![Frontier logo]()
$181
This Southwest deal was found by Cheapflights users on 3/22. 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.
Di 5/52:20 pm
DEN
- MDW
1 stop4h 30m
Southwest
Do 5/79:35 pm
MDW
- DEN
Nonstop2h 40m
Southwest
Deal found 3/22![Southwest logo]()
$181
Best flights from Wyoming to ChicagoDiscover carefully curated flight deals from Wyoming to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated März 24, 2026.
Discover carefully curated flight deals from Wyoming to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated März 24, 2026.
This United Airlines deal was found by Cheapflights users on 3/23. 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.
Mo 6/87:10 pm
DEN
- ORD
Nonstop2h 39m
United Airlines
Do 6/1110:55 pm
ORD
- DEN
Nonstop2h 58m
United Airlines
Deal found 3/23![United Airlines logo]()
$191
This Southwest deal was found by Cheapflights users on 3/23. 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.
Mi 5/206:15 am
DEN
- ORD
1 stop6h 00m
Southwest
Mo 6/12:40 pm
ORD
- DEN
2 stops10h 05m
Southwest
Deal found 3/23![Southwest logo]()
$200
This Delta deal was found by Cheapflights users on 3/23. 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.
Do 6/112:15 pm
DEN
- ORD
1 stop6h 58m
Delta
Mo 6/155:57 pm
ORD
- DEN
1 stop6h 53m
Delta
Deal found 3/23![Delta logo]()
$238
This Kiwi.com deal was found by Cheapflights users on 3/23. 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.
Mi 4/222:37 pm
DEN
- RFD
1 stop20h 23m
Multiple Airlines
So 4/2610:37 am
RFD
- DEN
2 stops26h 15m
Multiple Airlines
Deal found 3/23![Multiple Airlines logo]()
$343
This Southwest deal was found by Cheapflights users on 3/22. 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.
Di 4/2111:00 am
DEN
- MDW
2 stops5h 10m
Southwest
So 4/266:00 am
MDW
- DEN
Nonstop2h 40m
Southwest
Deal found 3/22![Southwest logo]()
$213
This Alaska Airlines deal was found by Cheapflights users on 3/21. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fr 9/1810:51 am
SLC
- ORD
1 stop7h 04m
Alaska Airlines
So 9/209:20 am
ORD
- SLC
1 stop10h 04m
Alaska Airlines
Deal found 3/21![Alaska Airlines logo]()
$471
This Southwest deal was found by Cheapflights users on 3/19. 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.
Sa 5/1611:40 am
DEN
- MDW
1 stop4h 35m
Southwest
Di 5/198:50 pm
MDW
- DEN
Nonstop2h 45m
Southwest
Deal found 3/19![Southwest logo]()
$215
This Southwest deal was found by Cheapflights users on 3/19. 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.
Sa 5/92:20 pm
DEN
- MDW
Nonstop2h 20m
Southwest
Sa 5/165:30 pm
MDW
- DEN
Nonstop2h 40m
Southwest
Deal found 3/19![Southwest logo]()
$217
This Delta deal was found by Cheapflights users on 3/19. 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.
Do 5/76:05 am
DEN
- ORD
1 stop5h 56m
Delta
Mo 5/115:19 pm
ORD
- DEN
1 stop6h 39m
Delta
Deal found 3/19![Delta logo]()
$265
This Southwest deal was found by Cheapflights users on 3/24. 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.
Fr 5/15:30 pm
DEN
- MDW
1 stop5h 25m
Southwest
Mo 5/49:35 pm
MDW
- DEN
Nonstop2h 40m
Southwest
Deal found 3/24![Southwest logo]()
$217
This Southwest deal was found by Cheapflights users on 3/21. 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.
Di 5/55:55 pm
DEN
- MDW
Nonstop2h 35m
Southwest
Di 5/125:30 pm
MDW
- DEN
Nonstop2h 40m
Southwest
Deal found 3/21![Southwest logo]()
$217
This Delta deal was found by Cheapflights users on 3/22. 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.
Do 6/1812:59 am
DEN
- ORD
1 stop6h 06m
Delta
Mo 6/225:22 pm
ORD
- DEN
1 stop6h 31m
Delta
Deal found 3/22![Delta logo]()
$291
This United Airlines deal was found by Cheapflights users on 3/22. 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.
Mi 7/224:23 pm
JAC
- ORD
1 stop7h 21m
United Airlines
Di 7/284:21 pm
ORD
- JAC
Nonstop3h 21m
United Airlines
Deal found 3/22![United Airlines logo]()
$329
This Delta deal was found by Cheapflights users on 3/21. 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.
Mi 6/1712:59 am
DEN
- ORD
1 stop6h 06m
Delta
Mo 6/225:22 pm
ORD
- DEN
1 stop6h 31m
Delta
Deal found 3/21![Delta logo]()
$291
This Southwest deal was found by Cheapflights users on 3/19. 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.
Sa 4/1810:50 am
DEN
- ORD
Nonstop2h 30m
Southwest
Mi 4/226:15 am
ORD
- DEN
1 stop7h 50m
Southwest
Deal found 3/19![Southwest logo]()
$219
This Kiwi.com deal was found by Cheapflights users on 3/20. 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.
Do 4/2312:02 pm
DEN
- RFD
2 stops29h 17m
Multiple Airlines
Mo 4/278:35 pm
RFD
- DEN
1 stop14h 08m
Multiple Airlines
Deal found 3/20![Multiple Airlines logo]()
$356
This United Airlines deal was found by Cheapflights users on 3/23. 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.
Sa 4/255:30 am
LAR
- ORD
1 stop4h 53m
United Airlines
Mi 4/292:05 pm
ORD
- LAR
1 stop8h 54m
United Airlines
Deal found 3/23![United Airlines logo]()
$335
This Southwest deal was found by Cheapflights users on 3/19. 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.
Do 6/47:05 pm
DEN
- MDW
1 stop4h 55m
Southwest
Mo 6/85:15 am
MDW
- DEN
Nonstop2h 35m
Southwest
Deal found 3/19![Southwest logo]()
$231
This Delta deal was found by Cheapflights users on 3/22. 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.
Fr 5/11:00 pm
JAC
- ORD
1 stop7h 18m
Delta
Mo 5/47:35 am
ORD
- JAC
1 stop5h 29m
Delta
Deal found 3/22![Delta logo]()
$339
This Southwest deal was found by Cheapflights users on 3/19. 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.
So 4/2611:25 am
DEN
- ORD
Nonstop2h 35m
Southwest
Di 4/284:50 pm
ORD
- DEN
1 stop7h 30m
Southwest
Deal found 3/19![Southwest logo]()
$233
This United Airlines deal was found by Cheapflights users on 3/19. 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.
Sa 4/185:30 am
LAR
- ORD
1 stop16h 28m
United Airlines
Mi 4/222:35 pm
ORD
- LAR
1 stop8h 24m
United Airlines
Deal found 3/19![United Airlines logo]()
$395
This Kiwi.com deal was found by Cheapflights users on 3/24. 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.
Fr 5/89:03 am
DEN
- RFD
1 stop9h 42m
Multiple Airlines
So 5/1010:37 am
RFD
- DEN
2 stops13h 02m
Multiple Airlines
Deal found 3/24![Multiple Airlines logo]()
$443
This Delta deal was found by Cheapflights users on 3/22. 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.
Di 4/217:20 am
JAC
- ORD
2 stops10h 32m
Delta
Di 4/287:35 am
ORD
- JAC
1 stop5h 29m
Delta
Deal found 3/22![Delta logo]()
$344
This Southwest deal was found by Cheapflights users on 3/19. 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.
Sa 5/235:20 am
DEN
- ORD
1 stop9h 10m
Southwest
Di 5/263:45 pm
ORD
- DEN
1 stop6h 10m
Southwest
Deal found 3/19![Southwest logo]()
$236
This United Airlines deal was found by Cheapflights users on 3/23. 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.
Do 6/44:23 pm
JAC
- ORD
1 stop5h 56m
United Airlines
Fr 6/54:21 pm
ORD
- JAC
Nonstop3h 21m
United Airlines
Deal found 3/23![United Airlines logo]()
$395
This Southwest deal was found by Cheapflights users on 3/21. 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.
Mi 4/1511:25 am
DEN
- ORD
Nonstop2h 35m
Southwest
Di 4/2110:30 am
ORD
- DEN
Nonstop2h 45m
Southwest
Deal found 3/21![Southwest logo]()
$237
This Kiwi.com deal was found by Cheapflights users on 3/24. 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.
Fr 5/159:03 am
DEN
- RFD
1 stop9h 42m
Multiple Airlines
So 5/1710:37 am
RFD
- DEN
2 stops13h 02m
Multiple Airlines
Deal found 3/24![Multiple Airlines logo]()
$465
This Delta deal was found by Cheapflights users on 3/24. 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.
Mi 5/61:09 pm
JAC
- ORD
1 stop7h 36m
Delta
Sa 5/93:47 pm
ORD
- JAC
1 stop5h 28m
Delta
Deal found 3/24![Delta logo]()
$354
This United Airlines deal was found by Cheapflights users on 3/23. 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.
Di 5/125:30 am
LAR
- ORD
1 stop5h 23m
United Airlines
Mo 5/181:43 pm
ORD
- LAR
1 stop4h 41m
United Airlines
Deal found 3/23![United Airlines logo]()
$408
This Southwest deal was found by Cheapflights users on 3/21. 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.
Sa 5/911:40 am
DEN
- MDW
1 stop4h 35m
Southwest
Mo 5/116:00 am
MDW
- DEN
Nonstop2h 40m
Southwest
Deal found 3/21![Southwest logo]()
$237
Last-minute flights from Wyoming to ChicagoDiscover last-minute flight deals from Wyoming to Chicago. Data last updated März 24, 2026 and is based on user searches.
Discover last-minute flight deals from Wyoming to Chicago. Data last updated März 24, 2026 and is based on user searches.
This Super.com deal was found by Cheapflights users on 3/24. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sa 4/49:00 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Mi 4/83:29 pm
ORD
- DEN
Nonstop3h 08m
Frontier
Deal found 3/24![Frontier logo]()
$176
This Kiwi.com deal was found by Cheapflights users on 3/20. 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.
Di 4/74:34 pm
DEN
- ORD
1 stop6h 06m
Frontier
Do 4/96:00 pm
ORD
- DEN
1 stop6h 58m
Frontier
Deal found 3/20![Frontier logo]()
$178
This Frontier deal was found by Cheapflights users on 3/23. 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.
Mi 4/84:34 pm
DEN
- ORD
1 stop6h 06m
Frontier
Di 4/2110:45 am
ORD
- DEN
1 stop12h 44m
Frontier
Deal found 3/23![Frontier logo]()
$181
This Super.com deal was found by Cheapflights users on 3/22. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sa 4/119:00 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Mo 4/132:29 pm
ORD
- DEN
Nonstop3h 11m
Frontier
Deal found 3/22![Frontier logo]()
$177
This Southwest deal was found by Cheapflights users on 3/23. 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.
Do 4/168:20 pm
DEN
- MDW
Nonstop2h 20m
Southwest
Di 4/2112:35 pm
MDW
- DEN
Nonstop2h 35m
Southwest
Deal found 3/23![Southwest logo]()
$175
This Kiwi.com deal was found by Cheapflights users on 3/23. 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.
Do 4/166:15 am
DEN
- ORD
Nonstop2h 35m
Multiple Airlines
Mo 4/209:44 pm
ORD
- DEN
1 stop13h 40m
Multiple Airlines
Deal found 3/23![Multiple Airlines logo]()
$182
This Cheapflightsfares deal was found by Cheapflights users on 3/23. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fr 4/1712:14 pm
DEN
- ORD
1 stop9h 39m
Frontier
So 4/193:08 pm
ORD
- DEN
1 stop18h 47m
Frontier
Deal found 3/23![Frontier logo]()
$179
This American Airlines deal was found by Cheapflights users on 3/24. 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.
Sa 4/187:36 am
DEN
- ORD
Nonstop2h 36m
American Airlines
Di 4/218:52 pm
ORD
- DEN
Nonstop2h 53m
American Airlines
Deal found 3/24![American Airlines logo]()
$175
This Southwest deal was found by Cheapflights users on 3/23. 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.
Mi 4/226:35 am
DEN
- MDW
Nonstop2h 20m
Southwest
Sa 4/2510:15 am
MDW
- DEN
1 stop5h 25m
Southwest
Deal found 3/23![Southwest logo]()
$181
This Expedia deal was found by Cheapflights users on 3/20. 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.
Do 4/236:30 am
DEN
- MDW
1 stop7h 34m
Frontier
Sa 4/256:00 am
MDW
- DEN
1 stop7h 14m
Frontier
Deal found 3/20![Frontier logo]()
$180
This Booking.com deal was found by Cheapflights users on 3/22. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Do 4/231:09 pm
DEN
- MDW
1 stop8h 10m
Frontier
Di 4/282:15 pm
MDW
- DEN
1 stop9h 14m
Frontier
Deal found 3/22![Frontier logo]()
$182
This Frontier deal was found by Cheapflights users on 3/20. 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.
Fr 4/2411:59 pm
DEN
- ORD
1 stop10h 34m
Frontier
Mo 4/274:28 pm
ORD
- DEN
1 stop7h 01m
Frontier
Deal found 3/20![Frontier logo]()
$180
One-way flights from Wyoming to ChicagoSearch for one-way flight options from Wyoming to Chicago. Find affordable one-way fares based on user searches. Data last updated März 24, 2026.
Search for one-way flight options from Wyoming to Chicago. Find affordable one-way fares based on user searches. Data last updated März 24, 2026.
This Frontier deal was found by Cheapflights users on 3/20. 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.
So 5/1711:54 pm
DEN
- ORD
1 stop7h 01m
Frontier
Deal found 3/20![Frontier logo]()
$90
This Frontier deal was found by Cheapflights users on 3/24. 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.
Mo 4/201:07 pm
DEN
- MDW
1 stop8h 12m
Frontier
Deal found 3/24![Frontier logo]()
$90
This Frontier deal was found by Cheapflights users on 3/20. 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.
Fr 5/811:54 pm
DEN
- ORD
1 stop7h 01m
Frontier
Deal found 3/20![Frontier logo]()
$91
This Trip.com deal was found by Cheapflights users on 3/21. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Do 4/306:00 am
DEN
- MDW
1 stop7h 32m
Frontier
Deal found 3/21![Frontier logo]()
$92
This Super.com deal was found by Cheapflights users on 3/19. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fr 4/176:15 am
DEN
- ORD
Nonstop2h 35m
Frontier
Deal found 3/19![Frontier logo]()
$93
This Trip.com deal was found by Cheapflights users on 3/23. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mi 5/65:05 am
DEN
- MDW
1 stop8h 07m
Frontier
Deal found 3/23![Frontier logo]()
$93
This Super.com deal was found by Cheapflights users on 3/24. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Do 5/146:30 am
DEN
- ORD
1 stop12h 21m
Frontier
Deal found 3/24![Frontier logo]()
$94
This Super.com deal was found by Cheapflights users on 3/24. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fr 5/811:54 pm
DEN
- MDW
1 stop10h 10m
Frontier
Deal found 3/24![Frontier logo]()
$94
This Mytrip deal was found by Cheapflights users on 3/21. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mo 4/139:45 am
DEN
- ORD
Nonstop2h 34m
Frontier
Deal found 3/21![Frontier logo]()
$95
This Southwest deal was found by Cheapflights users on 3/23. 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.
Mi 4/228:40 am
DEN
- MDW
2 stops5h 15m
Southwest
Deal found 3/23![Southwest logo]()
$95
This Cheapflightsfares deal was found by Cheapflights users on 3/20. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Do 5/285:27 pm
DEN
- ORD
1 stop28h 34m
Frontier
Deal found 3/20![Frontier logo]()
$96
This Frontier deal was found by Cheapflights users on 3/23. 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.
Mo 5/1811:54 pm
DEN
- MDW
1 stop10h 18m
Frontier
Deal found 3/23![Frontier logo]()
$96
Find flight deals from Wyoming to Chicago
Keep the following information in mind while searching for Wyoming to Chicago flight deals. Data was last updated März 24, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $174 (Southwest) |
One-way from | $90 (Frontier) |
Popular in | January |
Cheapest in | September |
Average price | $530 |
Good round-trip deal | $381 or less |
Good one-way deal | $291 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Wyoming 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 März 24, 2026.
Use the filters below to find and compare flights from Wyoming to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
DenverChicago
DEN - ORD
DENORD
Denver Intl
Mo 6/8
7:10 pm-10:49 pm
Nonstop2h 39m
Chicago O'Hare Intl
Do 6/11
10:55 pm-12:53 am
Nonstop2h 58m
$191
DenverChicago
DEN - ORD
DENORD
Denver Intl
Mi 5/20
6:15 am-1:15 pm
1 stop6h 00m
Chicago O'Hare Intl
Mo 6/1
2:40 pm-11:45 pm
2 stops10h 05m
$200
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Di 4/21
11:00 am-5:10 pm
2 stops5h 10m
Chicago Midway
So 4/26
6:00 am-7:40 am
Nonstop2h 40m
$213
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Sa 5/16
11:40 am-5:15 pm
1 stop4h 35m
Chicago Midway
Di 5/19
8:50 pm-10:35 pm
Nonstop2h 45m
$215
Quickest round-trip
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Sa 5/9
2:20 pm-5:40 pm
Nonstop2h 20m
Chicago Midway
Sa 5/16
5:30 pm-7:10 pm
Nonstop2h 40m
$217
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Fr 5/1
5:30 pm-11:55 pm
1 stop5h 25m
Chicago Midway
Mo 5/4
9:35 pm-11:15 pm
Nonstop2h 40m
$217
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Di 5/5
5:55 pm-9:30 pm
Nonstop2h 35m
Chicago Midway
Di 5/12
5:30 pm-7:10 pm
Nonstop2h 40m
$217
DenverChicago
DEN - ORD
DENORD
Denver Intl
Sa 4/18
10:50 am-2:20 pm
Nonstop2h 30m
Chicago O'Hare Intl
Mi 4/22
6:15 am-1:05 pm
1 stop7h 50m
$219
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Do 6/4
7:05 pm-1:00 am
1 stop4h 55m
Chicago Midway
Mo 6/8
5:15 am-6:50 am
Nonstop2h 35m
$231
DenverChicago
DEN - ORD
DENORD
Denver Intl
So 4/26
11:25 am-3:00 pm
Nonstop2h 35m
Chicago O'Hare Intl
Di 4/28
4:50 pm-11:20 pm
1 stop7h 30m
$233
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Wyoming to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Wyoming with our price prediction graph.
DEN-ORD
DEN-RFD
DEN-MDW
SLC-ORD
JAC-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 Wyoming to Chicago
USWY-CHI
DEN-ORD
DEN-RFD
DEN-MDW
SLC-ORD
What is the cheapest month to book a flight from Wyoming to Chicago?
Currently, September is the cheapest month in which you can book a flight from Wyoming to Chicago (average of $197). Flying from Wyoming to Chicago in July is currently the most expensive (average of $447). 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 WY to CHI?
Find hourly flight availability from Wyoming 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 März 24, 2026.
When flying from Wyoming to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
Weekly flight availability from Wyoming to Chicago
Explore weekly flight availability from Wyoming 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 März 24, 2026.
The most flights from USWY to CHI are scheduled on a Monday (5 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (2 on average).
Related info for your journey
Find useful and relevant information for your journey from Wyoming 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 locationsLansing
Merrillville
Hammond
Porter
Benton Harbor
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
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Alternative routes for Wyoming 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 März 24, 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 Wyoming to Chicago by cabin class
Find flights from Wyoming to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Wyoming and Chicago flights
Browse other Wyoming and Chicago flight options. Last updated on März 24, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Wyoming to Chicago flights
Consider these flights traveling from Wyoming to Chicago.
Top 2 airlines flying from Wyoming to Chicago
Discover the top 2 airlines that operate flights from Wyoming 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 März 24, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$191 | Average$370 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$281 | Average$385 | FlexibilityNo cancel fee | On-time69% |