$105+ Cheap flights from Wyoming to Chicago (CHI)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/17. Fares are subject to change and may not be available on all flights or dates of travel.
JAC — CHI
Oct 19 — Oct 261
Round-trip
1 adult, Economy
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Find cheap flights from Wyoming 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
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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 September 19, 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 September 19, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 10/128:55 pm -
Nonstop2h 29m
Wed 10/147:44 pm -
1 stop13h 22m
Deal found 9/15![Frontier logo]()
$169
This Frontier deal was found by Cheapflights users on 9/16. 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.
Wed 10/214:12 pm -
1 stop7h 14m
Wed 10/282:11 pm -
1 stop10h 11m
Deal found 9/16![Frontier logo]()
$170
This Frontier deal was found by Cheapflights users on 9/16. 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 10/238:55 pm -
Nonstop2h 29m
Sat 10/247:44 pm -
1 stop13h 22m
Deal found 9/16![Frontier logo]()
$171
This Super.com deal was found by Cheapflights users on 9/17. 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.
Tue 10/68:55 pm -
Nonstop2h 28m
Thu 10/86:30 am -
Nonstop2h 49m
Deal found 9/17![Frontier logo]()
$172
This Frontier deal was found by Cheapflights users on 9/17. 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.
Sat 10/176:10 am -
1 stop7h 15m
Mon 10/197:44 pm -
1 stop13h 22m
Deal found 9/17![Frontier logo]()
$173
This Expedia deal was found by Cheapflights users on 9/15. 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.
Thu 10/2910:41 am -
1 stop6h 06m
Sat 10/3112:20 pm -
1 stop10h 22m
Deal found 9/15![Frontier logo]()
$173
This Super.com deal was found by Cheapflights users on 9/16. 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.
Thu 10/158:55 pm -
Nonstop2h 29m
Sun 10/186:30 am -
Nonstop2h 49m
Deal found 9/16![Frontier logo]()
$174
This Mytrip deal was found by Cheapflights users on 9/17. 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.
Mon 10/56:13 pm -
2 stops16h 38m
Wed 10/76:30 am -
Nonstop2h 45m
Deal found 9/17![Frontier logo]()
$175
This Mytrip deal was found by Cheapflights users on 9/17. 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.
Tue 10/278:55 pm -
Nonstop2h 26m
Tue 11/39:51 am -
2 stops12h 41m
Deal found 9/17![Frontier logo]()
$176
This Expedia deal was found by Cheapflights users on 9/15. 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.
Mon 10/2610:38 am -
1 stop12h 05m
Thu 10/2912:20 pm -
1 stop10h 22m
Deal found 9/15![Frontier logo]()
$176
This CheapOair deal was found by Cheapflights users on 9/16. 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.
Fri 10/169:19 pm -
1 stop20h 48m
Sun 10/186:30 am -
Nonstop2h 49m
Deal found 9/16![Frontier logo]()
$177
This Frontier deal was found by Cheapflights users on 9/14. 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.
Sat 10/108:55 pm -
Nonstop2h 29m
Wed 10/148:30 am -
1 stop8h 24m
Deal found 9/14![Frontier logo]()
$178
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 September 19, 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 September 19, 2026.
This Southwest deal was found by Cheapflights users on 9/15. 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 10/298:55 pm -
Nonstop2h 25m
Sat 10/3112:50 pm -
1 stop3h 50m
Deal found 9/15![Southwest logo]()
$208
This Delta deal was found by Cheapflights users on 9/15. 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.
Thu 10/221:25 pm -
1 stop7h 02m
Mon 10/263:30 pm -
1 stop5h 36m
Deal found 9/15![Delta logo]()
$235
This United Airlines deal was found by Cheapflights users on 9/16. 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 10/164:40 pm -
Nonstop2h 42m
Sun 10/186:00 am -
Nonstop2h 39m
Deal found 9/16![United Airlines logo]()
$286
This Expedia deal was found by Cheapflights users on 9/13. 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.
Fri 10/161:47 pm -
1 stop10h 12m
Mon 10/196:30 am -
1 stop9h 51m
Deal found 9/13![Frontier logo]()
$342
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 10/2010:44 pm -
1 stop13h 33m
Sun 10/2510:20 am -
2 stops22h 46m
Deal found 9/17![Multiple Airlines logo]()
$352
This Alaska Airlines deal was found by Cheapflights users on 9/15. 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.
Fri 10/236:07 pm -
1 stop18h 18m
Sun 10/256:00 am -
1 stop9h 06m
Deal found 9/15![Alaska Airlines logo]()
$357
This Southwest deal was found by Cheapflights users on 9/15. 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 10/137:00 am -
Nonstop2h 20m
Tue 10/134:50 pm -
1 stop5h 05m
Deal found 9/15![Southwest logo]()
$212
This Delta deal was found by Cheapflights users on 9/15. 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.
Fri 12/41:26 pm -
1 stop5h 17m
Tue 12/811:39 am -
1 stop6h 32m
Deal found 9/15![Delta logo]()
$235
This Southwest deal was found by Cheapflights users on 9/14. 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 10/272:20 pm -
1 stop4h 25m
Thu 10/296:05 am -
Nonstop2h 40m
Deal found 9/14![Southwest logo]()
$215
This Southwest deal was found by Cheapflights users on 9/17. 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 11/711:45 am -
1 stop4h 20m
Mon 11/912:45 pm -
1 stop4h 50m
Deal found 9/17![Southwest logo]()
$220
This Delta deal was found by Cheapflights users on 9/15. 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 11/246:15 am -
1 stop6h 44m
Wed 12/25:33 pm -
1 stop7h 17m
Deal found 9/15![Delta logo]()
$262
This Southwest deal was found by Cheapflights users on 9/17. 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.
Fri 10/168:55 pm -
Nonstop2h 25m
Sat 10/172:20 pm -
1 stop5h 20m
Deal found 9/17![Southwest logo]()
$233
This Delta deal was found by Cheapflights users on 9/15. 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 11/76:20 am -
1 stop5h 39m
Sun 11/86:20 am -
1 stop4h 42m
Deal found 9/15![Delta logo]()
$272
This United Airlines deal was found by Cheapflights users on 9/15. 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 2/35:30 am -
1 stop8h 25m
Sat 2/64:07 pm -
1 stop6h 49m
Deal found 9/15![United Airlines logo]()
$334
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 10/2210:44 pm -
1 stop11h 43m
Sun 10/258:53 pm -
2 stops20h 03m
Deal found 9/16![Multiple Airlines logo]()
$364
This Southwest deal was found by Cheapflights users on 9/18. 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 10/288:35 am -
Nonstop2h 20m
Tue 11/31:20 pm -
1 stop5h 05m
Deal found 9/18![Southwest logo]()
$249
This United Airlines deal was found by Cheapflights users on 9/17. 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 10/313:13 pm -
1 stop6h 33m
Wed 11/410:55 am -
1 stop4h 43m
Deal found 9/17![United Airlines logo]()
$338
This Delta deal was found by Cheapflights users on 9/15. 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.
Thu 10/221:25 pm -
1 stop7h 02m
Sun 10/256:20 am -
1 stop6h 44m
Deal found 9/15![Delta logo]()
$285
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 10/1510:44 pm -
1 stop11h 43m
Sun 10/189:33 pm -
1 stop21h 13m
Deal found 9/16![Multiple Airlines logo]()
$366
This Southwest deal was found by Cheapflights users on 9/13. 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 11/216:30 pm -
Nonstop2h 25m
Thu 11/263:45 pm -
Nonstop2h 45m
Deal found 9/13![Southwest logo]()
$273
This United Airlines deal was found by Cheapflights users on 9/18. 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 10/135:30 am -
1 stop4h 58m
Tue 10/204:20 pm -
1 stop6h 36m
Deal found 9/18![United Airlines logo]()
$369
This Southwest deal was found by Cheapflights users on 9/18. 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 11/261:35 pm -
Nonstop2h 15m
Tue 12/18:55 pm -
Nonstop2h 45m
Deal found 9/18![Southwest logo]()
$279
This United Airlines deal was found by Cheapflights users on 9/16. 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 1/136:30 pm -
1 stop4h 33m
Wed 5/52:18 pm -
1 stop8h 38m
Deal found 9/16![United Airlines logo]()
$374
This Delta deal was found by Cheapflights users on 9/17. 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.
Fri 10/95:55 pm -
Nonstop3h 10m
Thu 10/157:35 am -
Nonstop3h 40m
Deal found 9/17![Delta logo]()
$355
This Alaska Airlines deal was found by Cheapflights users on 9/18. 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.
Thu 11/127:33 am -
2 stops15h 16m
Tue 11/172:15 pm -
1 stop30h 04m
Deal found 9/18![Alaska Airlines logo]()
$528
This Southwest deal was found by Cheapflights users on 9/15. 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 10/176:55 am -
1 stop4h 10m
Mon 10/196:25 pm -
1 stop5h 15m
Deal found 9/15![Southwest logo]()
$282
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 10/297:30 am -
1 stop11h 00m
Sun 11/18:53 pm -
1 stop13h 55m
Deal found 9/15![Multiple Airlines logo]()
$457
This Delta deal was found by Cheapflights users on 9/18. 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 11/237:45 am -
Nonstop3h 18m
Thu 11/266:40 am -
1 stop10h 53m
Deal found 9/18![Delta logo]()
$363
This United Airlines deal was found by Cheapflights users on 9/15. 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 10/214:10 pm -
Nonstop3h 25m
Sun 10/258:50 am -
Nonstop3h 47m
Deal found 9/15![United Airlines logo]()
$403
This Southwest deal was found by Cheapflights users on 9/13. 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.
Fri 10/165:55 pm -
Nonstop2h 20m
Mon 10/196:05 am -
Nonstop2h 40m
Deal found 9/13![Southwest logo]()
$287
Last-minute flights from Wyoming to ChicagoDiscover last-minute flight deals from Wyoming to Chicago. Data last updated September 19, 2026 and is based on user searches.
Discover last-minute flight deals from Wyoming to Chicago. Data last updated September 19, 2026 and is based on user searches.
This Mytrip deal was found by Cheapflights users on 9/17. 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.
Mon 10/56:13 pm -
2 stops16h 38m
Wed 10/76:30 am -
Nonstop2h 45m
Deal found 9/17![Frontier logo]()
$175
This Super.com deal was found by Cheapflights users on 9/17. 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.
Tue 10/68:55 pm -
Nonstop2h 28m
Thu 10/86:30 am -
Nonstop2h 49m
Deal found 9/17![Frontier logo]()
$172
This Frontier deal was found by Cheapflights users on 9/13. 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.
Sat 10/108:55 pm -
Nonstop2h 29m
Mon 10/197:44 pm -
1 stop13h 22m
Deal found 9/13![Frontier logo]()
$178
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 10/128:55 pm -
Nonstop2h 29m
Wed 10/147:44 pm -
1 stop13h 22m
Deal found 9/15![Frontier logo]()
$169
This Super.com deal was found by Cheapflights users on 9/16. 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.
Thu 10/158:55 pm -
Nonstop2h 29m
Sun 10/186:30 am -
Nonstop2h 49m
Deal found 9/16![Frontier logo]()
$174
This CheapOair deal was found by Cheapflights users on 9/16. 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.
Fri 10/169:19 pm -
1 stop20h 48m
Sun 10/186:30 am -
Nonstop2h 49m
Deal found 9/16![Frontier logo]()
$177
This Frontier deal was found by Cheapflights users on 9/16. 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.
Sat 10/176:10 am -
1 stop7h 15m
Mon 10/197:44 pm -
1 stop13h 22m
Deal found 9/16![Frontier logo]()
$173
This Frontier deal was found by Cheapflights users on 9/16. 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.
Wed 10/216:10 am -
1 stop7h 15m
Sat 10/2412:37 pm -
1 stop10h 12m
Deal found 9/16![Frontier logo]()
$170
This Frontier deal was found by Cheapflights users on 9/16. 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 10/238:55 pm -
Nonstop2h 29m
Sat 10/247:44 pm -
1 stop13h 22m
Deal found 9/16![Frontier logo]()
$171
This Expedia deal was found by Cheapflights users on 9/15. 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.
Mon 10/2610:38 am -
1 stop12h 05m
Thu 10/2912:20 pm -
1 stop10h 22m
Deal found 9/15![Frontier logo]()
$176
This Mytrip deal was found by Cheapflights users on 9/17. 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.
Tue 10/278:55 pm -
Nonstop2h 26m
Tue 11/39:51 am -
2 stops12h 41m
Deal found 9/17![Frontier logo]()
$176
This Expedia deal was found by Cheapflights users on 9/15. 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.
Thu 10/2910:41 am -
1 stop6h 06m
Sat 10/3112:20 pm -
1 stop10h 22m
Deal found 9/15![Frontier logo]()
$173
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 September 19, 2026.
Search for one-way flight options from Wyoming to Chicago. Find affordable one-way fares based on user searches. Data last updated September 19, 2026.
This Southwest deal was found by Cheapflights users on 9/17. 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 10/176:55 am -
1 stop4h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Southwest logo]()
$105
This Cheapflightsfares deal was found by Cheapflights users on 9/18. 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.
Wed 11/45:17 pm -
1 stop25h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Frontier logo]()
$106
This Cheapflightsfares deal was found by Cheapflights users on 9/18. 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.
Wed 11/410:43 am -
1 stop12h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Frontier logo]()
$106
This Expedia deal was found by Cheapflights users on 9/15. 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 10/149:00 am -
1 stop20h 34m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Frontier logo]()
$107
This Frontier deal was found by Cheapflights users on 9/15. 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 10/1610:38 am -
1 stop12h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Frontier logo]()
$107
This Frontier deal was found by Cheapflights users on 9/18. 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 11/56:10 am -
1 stop12h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Frontier logo]()
$108
This Southwest deal was found by Cheapflights users on 9/16. 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 10/225:50 am -
Nonstop2h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Southwest logo]()
$108
This Mytrip deal was found by Cheapflights users on 9/17. 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.
Tue 10/69:16 pm -
2 stops17h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Frontier logo]()
$109
This Super.com deal was found by Cheapflights users on 9/16. 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.
Sun 11/18:55 pm -
Nonstop2h 26m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Frontier logo]()
$110
This Southwest deal was found by Cheapflights users on 9/16. 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 12/56:00 am -
2 stops7h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Southwest logo]()
$110
This Cheapflightsfares deal was found by Cheapflights users on 9/16. 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.
Sun 10/188:55 pm -
Nonstop2h 29m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Frontier logo]()
$111
This Mytrip deal was found by Cheapflights users on 9/18. 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.
Mon 10/59:16 pm -
2 stops13h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Frontier logo]()
$112
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 September 19, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $169 (Kiwi.com) |
One-way from | $105 (Southwest) |
Popular in | April |
Cheapest in | September |
Average price | $318 |
Good round-trip deal | $550 or less |
Good one-way deal | $302 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 7,457,451 searches. Data last updated September 19, 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 Denver Intl - MDW Chicago Midway
DENMDW
Denver Intl
Thu 10/22
5:50 am-9:10 am
Nonstop2h 20m
Chicago Midway
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$108
DenverChicago
DEN Denver Intl - MDW Chicago Midway
DENMDW
Denver Intl
Sat 10/17
6:55 am-12:05 pm
1 stop4h 10m
Chicago Midway
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$111
DenverChicago
DEN Denver Intl - MDW Chicago Midway
DENMDW
Denver Intl
Thu 10/15
5:55 pm-9:15 pm
Nonstop2h 20m
Chicago Midway
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$115
DenverChicago
DEN Denver Intl - ORD Chicago O'Hare Intl
DENORD
Denver Intl
Wed 10/21
12:59 am-7:41 am
1 stop5h 42m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$118
DenverChicago
DEN Denver Intl - ORD Chicago O'Hare Intl
DENORD
Denver Intl
Mon 12/14
11:13 am-7:43 pm
1 stop7h 30m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$118
DenverChicago
DEN Denver Intl - MDW Chicago Midway
DENMDW
Denver Intl
Thu 11/5
6:30 pm-1:10 am
1 stop5h 40m
Chicago Midway
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$125
DenverChicago
DEN Denver Intl - MDW Chicago Midway
DENMDW
Denver Intl
Fri 10/30
11:20 am-5:15 pm
1 stop4h 55m
Chicago Midway
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$126
Quickest round-trip
DenverChicago
DEN Denver Intl - MDW Chicago Midway
DENMDW
Denver Intl
Fri 11/27
8:40 pm-11:55 pm
Nonstop2h 15m
Chicago Midway
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$129
DenverChicago
DEN Denver Intl - MDW Chicago Midway
DENMDW
Denver Intl
Fri 10/16
11:20 am-5:15 pm
1 stop4h 55m
Chicago Midway
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$135
DenverChicago
DEN Denver Intl - ORD Chicago O'Hare Intl
DENORD
Denver Intl
Thu 11/5
6:42 pm-5:13 am
1 stop9h 31m
Chicago O'Hare Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$137
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-MDW
DEN-ORD
SLC-ORD
DEN-RFD
LAR-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-MDW
DEN-ORD
SLC-ORD
DEN-RFD
What is the cheapest month to book a flight from Wyoming to Chicago?
Currently, February is the cheapest month in which you can book a flight from Wyoming to Chicago (average of $370). Flying from Wyoming to Chicago in January is currently the most expensive (average of $609). 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 September 19, 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 September 19, 2026.
The most flights from USWY to CHI are scheduled on a Wednesday (8 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (3 on average).
How much does it cost to fly round-trip from Wyoming to Chicago?
Airfare is typical for this route at the moment.
Wyoming to Chicago flights typically cost between $314 and $435 in October.The cheapest round-trip price found within the last 5 days was $389 on United Airlines (Oct 16-Oct 19).
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 locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
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
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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 September 19, 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 September 19, 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 7,457,451 searches. Data last updated September 19, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$260 | Average$462 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$281 | Average$585 | FlexibilityNo cancel fee | On-time69% |