$92+ 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 7/16. Fares are subject to change and may not be available on all flights or dates of travel.
JAC — CHI
Jul 9 — Jul 161
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 June 9, 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 June 9, 2026.
This Super.com deal was found by Cheapflights users on 6/8. 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 6/305:05 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Wed 7/89:57 pm
ORD
- DEN
Nonstop3h 00m
Frontier
Deal found 6/8![Frontier logo]()
$181
This Frontier deal was found by Cheapflights users on 6/8. 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 6/295:05 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Tue 7/149:57 pm
ORD
- DEN
Nonstop3h 00m
Frontier
Deal found 6/8![Frontier logo]()
$182
This Cheapflightsfares deal was found by Cheapflights users on 6/7. 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.
Sat 7/45:05 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Wed 7/89:57 pm
ORD
- DEN
Nonstop3h 00m
Frontier
Deal found 6/7![Frontier logo]()
$183
This Southwest deal was found by Cheapflights users on 6/8. 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 8/68:25 pm
DEN
- MDW
Nonstop2h 20m
Southwest
Tue 8/113:50 pm
MDW
- DEN
Nonstop2h 30m
Southwest
Deal found 6/8![Southwest logo]()
$183
This Kiwi.com deal was found by Cheapflights users on 6/4. 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.
Tue 8/255:15 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Sat 8/299:48 pm
ORD
- DEN
Nonstop3h 06m
Frontier
Deal found 6/4![Frontier logo]()
$184
This Frontier deal was found by Cheapflights users on 6/7. 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 7/35:05 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Wed 7/89:57 pm
ORD
- DEN
Nonstop3h 00m
Frontier
Deal found 6/7![Frontier logo]()
$185
This Cheapflightsfares deal was found by Cheapflights users on 6/6. 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.
Tue 7/75:05 pm
DEN
- ORD
Nonstop2h 47m
Frontier
Wed 7/159:57 pm
ORD
- DEN
Nonstop3h 00m
Frontier
Deal found 6/6![Frontier logo]()
$186
This Frontier deal was found by Cheapflights users on 6/7. 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 7/225:05 pm
DEN
- ORD
Nonstop2h 47m
Frontier
Wed 7/299:57 pm
ORD
- DEN
Nonstop3h 00m
Frontier
Deal found 6/7![Frontier logo]()
$187
This Frontier deal was found by Cheapflights users on 6/9. 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 8/225:15 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Mon 8/249:48 pm
ORD
- DEN
Nonstop3h 06m
Frontier
Deal found 6/9![Frontier logo]()
$188
This Frontier deal was found by Cheapflights users on 6/8. 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 8/205:15 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Sat 8/229:48 pm
ORD
- DEN
Nonstop3h 06m
Frontier
Deal found 6/8![Frontier logo]()
$189
This Cheapflightsfares deal was found by Cheapflights users on 6/8. 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.
Tue 7/75:05 pm
DEN
- ORD
Nonstop2h 47m
Frontier
Tue 7/149:57 pm
ORD
- DEN
Nonstop3h 00m
Frontier
Deal found 6/8![Frontier logo]()
$191
This Frontier deal was found by Cheapflights users on 6/7. 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 7/65:05 pm
DEN
- ORD
Nonstop2h 47m
Frontier
Sat 7/189:57 pm
ORD
- DEN
Nonstop3h 00m
Frontier
Deal found 6/7![Frontier logo]()
$192
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 June 9, 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 June 9, 2026.
This Delta deal was found by Cheapflights users on 6/8. 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 8/612:59 am
DEN
- ORD
1 stop5h 57m
Delta
Mon 8/107:00 am
ORD
- DEN
1 stop7h 45m
Delta
Deal found 6/8![Delta logo]()
$227
This United Airlines deal was found by Cheapflights users on 6/8. 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 7/89:05 pm
DEN
- ORD
Nonstop2h 39m
United Airlines
Sun 7/125:00 am
ORD
- DEN
Nonstop2h 41m
United Airlines
Deal found 6/8![United Airlines logo]()
$241
This Southwest deal was found by Cheapflights users on 6/8. 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 7/158:10 am
DEN
- MDW
1 stop5h 25m
Southwest
Mon 7/205:15 am
MDW
- DEN
Nonstop2h 35m
Southwest
Deal found 6/8![Southwest logo]()
$251
This Kiwi.com deal was found by Cheapflights users on 6/7. 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 8/207:23 am
DEN
- RFD
1 stop6h 46m
Multiple Airlines
Sun 8/239:35 pm
RFD
- DEN
1 stop12h 55m
Multiple Airlines
Deal found 6/7![Multiple Airlines logo]()
$315
This American Airlines deal was found by Cheapflights users on 6/6. 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 9/113:41 pm
JAC
- ORD
Nonstop3h 29m
American Airlines
Sun 9/139:45 am
ORD
- JAC
Nonstop3h 22m
American Airlines
Deal found 6/6![American Airlines logo]()
$374
This Delta deal was found by Cheapflights users on 6/8. 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 8/612:59 am
DEN
- MDW
1 stop7h 18m
Delta
Mon 8/101:27 pm
MDW
- DEN
1 stop4h 56m
Delta
Deal found 6/8![Delta logo]()
$227
This Alaska Airlines deal was found by Cheapflights users on 6/5. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/253:47 pm
JAC
- ORD
1 stop12h 13m
Alaska Airlines
Fri 8/77:59 pm
ORD
- JAC
1 stop20h 08m
Alaska Airlines
Deal found 6/5![Alaska Airlines logo]()
$479
This United Airlines deal was found by Cheapflights users on 6/4. 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.
Wed 7/19:05 pm
DEN
- ORD
Nonstop2h 39m
United Airlines
Mon 7/65:00 am
ORD
- DEN
Nonstop2h 42m
United Airlines
Deal found 6/4![United Airlines logo]()
$241
This Southwest deal was found by Cheapflights users on 6/6. 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 8/297:15 am
DEN
- MDW
Nonstop2h 20m
Southwest
Tue 9/18:50 pm
MDW
- DEN
Nonstop2h 35m
Southwest
Deal found 6/6![Southwest logo]()
$255
This United Airlines deal was found by Cheapflights users on 6/6. 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 7/89:05 pm
DEN
- ORD
Nonstop2h 39m
United Airlines
Tue 7/149:50 pm
ORD
- DEN
Nonstop2h 58m
United Airlines
Deal found 6/6![United Airlines logo]()
$245
This Delta deal was found by Cheapflights users on 6/4. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/712:55 am
DEN
- ORD
1 stop6h 05m
Delta
Tue 10/138:55 am
ORD
- DEN
1 stop6h 08m
Delta
Deal found 6/4![Delta logo]()
$257
This Southwest deal was found by Cheapflights users on 6/4. 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 7/237:05 pm
DEN
- MDW
1 stop5h 00m
Southwest
Fri 7/249:25 pm
MDW
- DEN
Nonstop2h 45m
Southwest
Deal found 6/4![Southwest logo]()
$275
This United Airlines deal was found by Cheapflights users on 6/4. 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.
Fri 9/48:29 pm
DEN
- ORD
Nonstop2h 30m
United Airlines
Mon 9/710:00 pm
ORD
- DEN
Nonstop2h 53m
United Airlines
Deal found 6/4![United Airlines logo]()
$251
This Delta deal was found by Cheapflights users on 6/8. 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 7/1511:08 am
DEN
- ORD
1 stop4h 51m
Delta
Mon 7/205:54 pm
ORD
- DEN
1 stop6h 33m
Delta
Deal found 6/8![Delta logo]()
$261
This Southwest deal was found by Cheapflights users on 6/8. 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 7/177:05 pm
DEN
- MDW
1 stop5h 00m
Southwest
Mon 7/205:15 am
MDW
- DEN
Nonstop2h 35m
Southwest
Deal found 6/8![Southwest logo]()
$275
This United Airlines deal was found by Cheapflights users on 6/6. 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 8/295:48 pm
DEN
- ORD
Nonstop2h 42m
United Airlines
Tue 9/16:00 am
ORD
- DEN
Nonstop2h 39m
United Airlines
Deal found 6/6![United Airlines logo]()
$255
This Kiwi.com deal was found by Cheapflights users on 6/4. 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 7/87:56 am
DEN
- RFD
1 stop23h 33m
Multiple Airlines
Wed 7/1510:03 am
RFD
- DEN
2 stops11h 04m
Multiple Airlines
Deal found 6/4![Multiple Airlines logo]()
$363
This Delta deal was found by Cheapflights users on 6/6. 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 7/149:19 am
DEN
- ORD
1 stop6h 40m
Delta
Wed 7/226:30 am
ORD
- DEN
1 stop4h 33m
Delta
Deal found 6/6![Delta logo]()
$275
This United Airlines deal was found by Cheapflights users on 6/5. 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.
Tue 11/248:34 pm
DEN
- ORD
Nonstop2h 23m
United Airlines
Fri 11/275:00 am
ORD
- DEN
Nonstop2h 42m
United Airlines
Deal found 6/5![United Airlines logo]()
$255
This Southwest deal was found by Cheapflights users on 6/4. 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 7/305:15 pm
DEN
- MDW
1 stop4h 50m
Southwest
Sun 8/25:00 am
MDW
- DEN
2 stops8h 20m
Southwest
Deal found 6/4![Southwest logo]()
$286
This Kiwi.com deal was found by Cheapflights users on 6/6. 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 9/187:00 am
DEN
- RFD
1 stop10h 11m
Multiple Airlines
Sun 9/203:53 pm
RFD
- DEN
1 stop6h 56m
Multiple Airlines
Deal found 6/6![Multiple Airlines logo]()
$366
This Delta deal was found by Cheapflights users on 6/5. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/146:05 am
DEN
- ORD
1 stop5h 59m
Delta
Fri 9/185:42 pm
ORD
- DEN
1 stop6h 43m
Delta
Deal found 6/5![Delta logo]()
$281
This Southwest deal was found by Cheapflights users on 6/8. 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 9/166:45 am
SLC
- MDW
2 stops8h 15m
Southwest
Wed 9/236:40 am
MDW
- SLC
1 stop6h 25m
Southwest
Deal found 6/8![Southwest logo]()
$287
This Kiwi.com deal was found by Cheapflights users on 6/9. 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 9/176:30 am
DEN
- RFD
2 stops13h 09m
Multiple Airlines
Mon 9/218:44 pm
RFD
- DEN
1 stop22h 51m
Multiple Airlines
Deal found 6/9![Multiple Airlines logo]()
$376
This Southwest deal was found by Cheapflights users on 6/6. 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 9/711:00 am
DEN
- MDW
1 stop5h 00m
Southwest
Fri 9/112:05 pm
MDW
- DEN
Nonstop2h 30m
Southwest
Deal found 6/6![Southwest logo]()
$295
This Delta deal was found by Cheapflights users on 6/4. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/146:05 am
DEN
- MDW
1 stop5h 34m
Delta
Sun 8/167:25 pm
MDW
- DEN
1 stop5h 09m
Delta
Deal found 6/4![Delta logo]()
$295
This United Airlines deal was found by Cheapflights users on 6/8. 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 9/116:27 pm
LAR
- ORD
1 stop4h 32m
United Airlines
Mon 9/145:51 pm
ORD
- LAR
1 stop5h 05m
United Airlines
Deal found 6/8![United Airlines logo]()
$310
This Kiwi.com deal was found by Cheapflights users on 6/4. 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 10/812:17 pm
DEN
- RFD
2 stops22h 10m
Multiple Airlines
Sun 10/119:33 pm
RFD
- DEN
1 stop7h 19m
Multiple Airlines
Deal found 6/4![Multiple Airlines logo]()
$376
This Southwest deal was found by Cheapflights users on 6/6. 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 6/3010:25 am
DEN
- MDW
2 stops5h 35m
Southwest
Sat 7/115:05 pm
MDW
- DEN
1 stop3h 45m
Southwest
Deal found 6/6![Southwest logo]()
$304
This Kiwi.com deal was found by Cheapflights users on 6/4. 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 7/17:43 am
DEN
- RFD
1 stop23h 46m
Multiple Airlines
Sun 7/59:19 am
RFD
- DEN
1 stop6h 04m
Multiple Airlines
Deal found 6/4![Multiple Airlines logo]()
$377
Last-minute flights from Wyoming to ChicagoDiscover last-minute flight deals from Wyoming to Chicago. Data last updated June 9, 2026 and is based on user searches.
Discover last-minute flight deals from Wyoming to Chicago. Data last updated June 9, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 6/8. 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 6/145:05 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Sat 6/209:48 pm
ORD
- DEN
Nonstop3h 06m
Frontier
Deal found 6/8![Frontier logo]()
$229
This Kiwi.com deal was found by Cheapflights users on 6/7. 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 6/165:05 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Sat 6/279:48 pm
ORD
- DEN
Nonstop3h 06m
Frontier
Deal found 6/7![Frontier logo]()
$195
This Frontier deal was found by Cheapflights users on 6/7. 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 6/175:05 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Sat 6/279:48 pm
ORD
- DEN
Nonstop3h 06m
Frontier
Deal found 6/7![Frontier logo]()
$234
This Frontier deal was found by Cheapflights users on 6/8. 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 6/195:05 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Wed 7/89:57 pm
ORD
- DEN
Nonstop3h 00m
Frontier
Deal found 6/8![Frontier logo]()
$227
This Frontier deal was found by Cheapflights users on 6/7. 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 6/195:05 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Sat 6/279:48 pm
ORD
- DEN
Nonstop3h 06m
Frontier
Deal found 6/7![Frontier logo]()
$237
This Southwest deal was found by Cheapflights users on 6/4. 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 6/3012:20 pm
DEN
- MDW
1 stop3h 45m
Southwest
Wed 7/111:20 am
MDW
- DEN
Nonstop2h 30m
Southwest
Deal found 6/4![Southwest logo]()
$223
This Southwest deal was found by Cheapflights users on 6/4. 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 7/76:15 am
DEN
- MDW
Nonstop2h 25m
Southwest
Tue 7/149:05 pm
MDW
- DEN
Nonstop2h 50m
Southwest
Deal found 6/4![Southwest logo]()
$217
This Delta deal was found by Cheapflights users on 6/9. 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 7/76:00 am
DEN
- MDW
1 stop6h 09m
Delta
Tue 7/147:06 pm
MDW
- DEN
1 stop5h 21m
Delta
Deal found 6/9![Delta logo]()
$237
This Expedia deal was found by Cheapflights users on 6/8. 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 7/89:58 am
DEN
- MDW
1 stop11h 05m
Frontier
Wed 7/154:45 pm
MDW
- DEN
1 stop7h 10m
Frontier
Deal found 6/8![Frontier logo]()
$230
This Super.com deal was found by Cheapflights users on 6/7. 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 7/1410:09 am
DEN
- MDW
1 stop7h 28m
Frontier
Wed 7/226:05 am
MDW
- DEN
1 stop8h 55m
Frontier
Deal found 6/7![Frontier logo]()
$226
This Booking.com deal was found by Cheapflights users on 6/6. 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.
Tue 7/2110:09 am
DEN
- MDW
1 stop5h 42m
Frontier
Tue 7/2812:11 pm
MDW
- DEN
1 stop10h 54m
Frontier
Deal found 6/6![Frontier logo]()
$235
This Booking.com deal was found by Cheapflights users on 6/7. 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.
Wed 7/229:58 am
DEN
- MDW
1 stop11h 05m
Frontier
Wed 7/294:45 pm
MDW
- DEN
1 stop7h 10m
Frontier
Deal found 6/7![Frontier logo]()
$229
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 June 9, 2026.
Search for one-way flight options from Wyoming to Chicago. Find affordable one-way fares based on user searches. Data last updated June 9, 2026.
This Trip.com deal was found by Cheapflights users on 6/9. 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.
Thu 7/165:05 pm
DEN
- ORD
Nonstop2h 47m
Frontier
Deal found 6/9![Frontier logo]()
$92
This Kiwi.com deal was found by Cheapflights users on 6/4. 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.
Mon 8/1711:59 pm
DEN
- ORD
1 stop7h 04m
Frontier
Deal found 6/4![Frontier logo]()
$98
This Kiwi.com deal was found by Cheapflights users on 6/4. 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.
Mon 8/246:30 am
DEN
- MDW
1 stop14h 41m
Frontier
Deal found 6/4![Frontier logo]()
$98
This Delta deal was found by Cheapflights users on 6/9. 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 8/46:05 am
DEN
- ORD
1 stop6h 03m
Delta
Deal found 6/9![Delta logo]()
$99
This Delta deal was found by Cheapflights users on 6/8. 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 8/46:05 am
DEN
- MDW
1 stop5h 34m
Delta
Deal found 6/8![Delta logo]()
$99
This Super.com deal was found by Cheapflights users on 6/7. 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.
Sat 6/205:05 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Deal found 6/7![Frontier logo]()
$100
This Kiwi.com deal was found by Cheapflights users on 6/4. 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.
Tue 9/86:30 am
DEN
- MDW
1 stop27h 28m
Frontier
Deal found 6/4![Frontier logo]()
$100
This Kiwi.com deal was found by Cheapflights users on 6/4. 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 8/126:30 am
DEN
- ORD
1 stop12h 23m
Frontier
Deal found 6/4![Frontier logo]()
$101
This Kiwi.com deal was found by Cheapflights users on 6/4. 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 10/2111:48 pm
DEN
- MDW
1 stop10h 10m
Frontier
Deal found 6/4![Frontier logo]()
$101
This Cheapflightsfares deal was found by Cheapflights users on 6/8. 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.
Sat 7/45:05 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Deal found 6/8![Frontier logo]()
$104
This Southwest deal was found by Cheapflights users on 6/8. 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 8/108:25 pm
DEN
- MDW
Nonstop2h 20m
Southwest
Deal found 6/8![Southwest logo]()
$104
This United Airlines deal was found by Cheapflights users on 6/4. 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.
Wed 7/157:10 pm
DEN
- ORD
Nonstop2h 39m
United Airlines
Deal found 6/4![United Airlines logo]()
$109
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 June 9, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $181 (Super.com) |
One-way from | $92 (Trip.com) |
Popular in | April |
Cheapest in | September |
Average price | $462 |
Good round-trip deal | $505 or less |
Good one-way deal | $267 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 June 9, 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
Thu 8/6
12:59 am-7:56 am
1 stop5h 57m
Chicago O'Hare Intl
Mon 8/10
7:00 am-1:45 pm
1 stop7h 45m
$227
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Thu 8/6
12:59 am-9:17 am
1 stop7h 18m
Chicago Midway
Mon 8/10
1:27 pm-5:23 pm
1 stop4h 56m
$227
DenverChicago
DEN - ORD
DENORD
Denver Intl
Wed 7/8
9:05 pm-12:44 am
Nonstop2h 39m
Chicago O'Hare Intl
Sun 7/12
5:00 am-6:41 am
Nonstop2h 41m
$241
DenverChicago
DEN - ORD
DENORD
Denver Intl
Wed 7/1
9:05 pm-12:44 am
Nonstop2h 39m
Chicago O'Hare Intl
Mon 7/6
5:00 am-6:42 am
Nonstop2h 42m
$241
DenverChicago
DEN - ORD
DENORD
Denver Intl
Wed 7/8
9:05 pm-12:44 am
Nonstop2h 39m
Chicago O'Hare Intl
Tue 7/14
9:50 pm-11:48 pm
Nonstop2h 58m
$245
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Wed 7/15
8:10 am-2:35 pm
1 stop5h 25m
Chicago Midway
Mon 7/20
5:15 am-6:50 am
Nonstop2h 35m
$251
DenverChicago
DEN - ORD
DENORD
Denver Intl
Fri 9/4
8:29 pm-11:59 pm
Nonstop2h 30m
Chicago O'Hare Intl
Mon 9/7
10:00 pm-11:53 pm
Nonstop2h 53m
$251
Quickest round-trip
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Sat 8/29
7:15 am-10:35 am
Nonstop2h 20m
Chicago Midway
Tue 9/1
8:50 pm-10:25 pm
Nonstop2h 35m
$255
DenverChicago
DEN - ORD
DENORD
Denver Intl
Sat 8/29
5:48 pm-9:30 pm
Nonstop2h 42m
Chicago O'Hare Intl
Tue 9/1
6:00 am-7:39 am
Nonstop2h 39m
$255
DenverChicago
DEN - ORD
DENORD
Denver Intl
Tue 11/24
8:34 pm-11:57 pm
Nonstop2h 23m
Chicago O'Hare Intl
Fri 11/27
5:00 am-6:42 am
Nonstop2h 42m
$255
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-MDW
DEN-RFD
JAC-ORD
SLC-MDW
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-MDW
DEN-RFD
JAC-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 $191). Flying from Wyoming to Chicago in June is currently the most expensive (average of $383). 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 June 9, 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 June 9, 2026.
The most flights from USWY to CHI are scheduled on a Monday (9 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (6 on average).
How much does it cost to fly round-trip from Wyoming to Chicago?
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
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.
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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 June 9, 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 June 9, 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 June 9, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$229 | Average$404 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$281 | Average$387 | FlexibilityNo cancel fee | On-time69% |