$84+ 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 4/20. Fares are subject to change and may not be available on all flights or dates of travel.
JAC — CHI
Mar 9 — Mar 161
1 adult, Economy
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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 February 7, 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 February 7, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 2/4. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/2412:59 am
DEN
- ORD
1 stop8h 52m
Frontier
Sat 2/288:05 am
ORD
- DEN
1 stop25h 15m
Frontier
Deal found 2/4![Frontier logo]()
$127
This Cheapflightsfares deal was found by Cheapflights users on 2/4. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/57:35 pm
DEN
- ORD
Nonstop2h 39m
Frontier
Thu 3/1210:53 am
ORD
- DEN
Nonstop2h 59m
Frontier
Deal found 2/4![Frontier logo]()
$131
This Kiwi.com deal was found by Cheapflights users on 2/6. 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 2/279:41 am
DEN
- ORD
Nonstop2h 44m
Multiple Airlines
Tue 3/37:23 pm
ORD
- DEN
1 stop14h 48m
Multiple Airlines
Deal found 2/6![Multiple Airlines logo]()
$132
This Cheapflightsfares deal was found by Cheapflights users on 2/4. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/57:35 pm
DEN
- ORD
Nonstop2h 39m
Frontier
Wed 3/117:39 pm
ORD
- DEN
1 stop15h 05m
Frontier
Deal found 2/4![Frontier logo]()
$133
This Kiwi.com deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/279:41 am
DEN
- ORD
Nonstop2h 44m
Frontier
Mon 3/26:00 am
ORD
- DEN
1 stop26h 54m
Frontier
Deal found 2/4![Frontier logo]()
$134
This Kiwi.com deal was found by Cheapflights users on 2/7. 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.
Sat 3/710:20 am
DEN
- ORD
1 stop13h 01m
Frontier
Tue 3/104:28 pm
ORD
- DEN
1 stop15h 45m
Frontier
Deal found 2/7![Frontier logo]()
$135
This Super.com deal was found by Cheapflights users on 2/6. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/99:19 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Thu 3/1210:53 am
ORD
- DEN
Nonstop2h 59m
Frontier
Deal found 2/6![Frontier logo]()
$136
This Cheapflightsfares deal was found by Cheapflights users on 2/4. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/267:35 pm
DEN
- ORD
Nonstop2h 39m
Frontier
Mon 3/27:35 am
ORD
- DEN
1 stop25h 51m
Frontier
Deal found 2/4![Frontier logo]()
$137
This Cheapflightsfares deal was found by Cheapflights users on 2/7. 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.
Thu 4/236:15 am
DEN
- ORD
Nonstop2h 35m
Frontier
Mon 4/2710:55 am
ORD
- DEN
Nonstop3h 03m
Frontier
Deal found 2/7![Frontier logo]()
$138
This Kiwi.com deal was found by Cheapflights users on 2/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/611:59 pm
DEN
- ORD
1 stop10h 17m
Frontier
Fri 3/136:20 pm
ORD
- DEN
Nonstop3h 04m
Frontier
Deal found 2/5![Frontier logo]()
$139
This Kiwi.com deal was found by Cheapflights users on 2/4. 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 3/312:59 am
DEN
- MDW
1 stop17h 08m
Frontier
Wed 3/116:05 am
MDW
- DEN
1 stop17h 59m
Frontier
Deal found 2/4![Frontier logo]()
$139
This Cheapflightsfares deal was found by Cheapflights users on 2/4. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/246:15 am
DEN
- ORD
Nonstop2h 35m
Frontier
Sun 4/2610:55 am
ORD
- DEN
Nonstop3h 03m
Frontier
Deal found 2/4![Frontier logo]()
$141
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 February 7, 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 February 7, 2026.
This Southwest deal was found by Cheapflights users on 2/7. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/34:35 pm
DEN
- MDW
Nonstop2h 20m
Southwest
Sat 3/79:35 pm
MDW
- DEN
Nonstop2h 40m
Southwest
Deal found 2/7![Southwest logo]()
$179
This Kiwi.com deal was found by Cheapflights users on 2/6. 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.
Mon 3/98:38 am
SLC
- MDW
1 stop13h 42m
Frontier
Wed 3/1111:25 am
MDW
- SLC
2 stops13h 49m
Frontier
Deal found 2/6![Frontier logo]()
$179
This United Airlines deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/266:00 am
DEN
- ORD
Nonstop2h 38m
United Airlines
Tue 3/315:45 pm
ORD
- DEN
Nonstop2h 55m
United Airlines
Deal found 2/3![United Airlines logo]()
$191
This Delta deal was found by Cheapflights users on 2/6. 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 4/146:20 am
DEN
- ORD
1 stop5h 25m
Delta
Tue 4/145:53 pm
ORD
- DEN
1 stop7h 40m
Delta
Deal found 2/6![Delta logo]()
$205
This Alaska Airlines deal was found by Cheapflights users on 2/4. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/256:20 am
SLC
- ORD
1 stop9h 13m
Alaska Airlines
Tue 3/35:29 pm
ORD
- SLC
1 stop19h 19m
Alaska Airlines
Deal found 2/4![Alaska Airlines logo]()
$217
This American Airlines deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/111:44 pm
JAC
- ORD
Nonstop3h 13m
American Airlines
Mon 3/239:54 am
ORD
- JAC
Nonstop3h 24m
American Airlines
Deal found 2/4![American Airlines logo]()
$311
This Kiwi.com deal was found by Cheapflights users on 2/6. 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 2/2010:30 pm
DEN
- RFD
1 stop11h 40m
Multiple Airlines
Mon 2/237:51 pm
RFD
- DEN
1 stop13h 03m
Multiple Airlines
Deal found 2/6![Multiple Airlines logo]()
$312
This Southwest deal was found by Cheapflights users on 2/6. 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 3/72:45 pm
DEN
- ORD
1 stop8h 10m
Southwest
Sat 3/143:45 pm
ORD
- DEN
1 stop9h 05m
Southwest
Deal found 2/6![Southwest logo]()
$182
This Sun Country Air deal was found by Cheapflights users on 2/6. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/226:16 pm
SLC
- ORD
1 stop22h 23m
Sun Country Air
Mon 7/276:25 pm
ORD
- SLC
1 stop23h 47m
Sun Country Air
Deal found 2/6![Sun Country Air logo]()
$365
This United Airlines deal was found by Cheapflights users on 2/4. 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.
Sat 5/169:20 pm
DEN
- ORD
Nonstop2h 38m
United Airlines
Tue 5/199:34 pm
ORD
- DEN
Nonstop2h 56m
United Airlines
Deal found 2/4![United Airlines logo]()
$192
This Southwest deal was found by Cheapflights users on 2/7. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/72:45 pm
DEN
- ORD
1 stop8h 10m
Southwest
Tue 3/104:50 pm
ORD
- DEN
Nonstop2h 45m
Southwest
Deal found 2/7![Southwest logo]()
$189
This Delta deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/112:35 am
DEN
- MDW
1 stop7h 18m
Delta
Mon 4/67:20 pm
MDW
- DEN
1 stop5h 19m
Delta
Deal found 2/3![Delta logo]()
$211
This United Airlines deal was found by Cheapflights users on 2/6. 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 3/286:00 am
DEN
- ORD
Nonstop2h 38m
United Airlines
Tue 3/312:05 pm
ORD
- DEN
Nonstop2h 55m
United Airlines
Deal found 2/6![United Airlines logo]()
$195
This Southwest deal was found by Cheapflights users on 2/6. 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 4/1810:50 am
DEN
- ORD
Nonstop2h 30m
Southwest
Wed 4/2210:30 am
ORD
- DEN
Nonstop2h 45m
Southwest
Deal found 2/6![Southwest logo]()
$190
This Alaska Airlines deal was found by Cheapflights users on 2/6. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/277:08 am
SLC
- ORD
1 stop15h 51m
Alaska Airlines
Fri 3/63:07 pm
ORD
- SLC
1 stop9h 38m
Alaska Airlines
Deal found 2/6![Alaska Airlines logo]()
$233
This United Airlines deal was found by Cheapflights users on 2/6. 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.
Mon 3/98:23 pm
DEN
- ORD
Nonstop2h 30m
United Airlines
Sat 3/142:01 pm
ORD
- DEN
Nonstop2h 55m
United Airlines
Deal found 2/6![United Airlines logo]()
$195
This Southwest deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/266:50 pm
DEN
- MDW
Nonstop2h 15m
Southwest
Tue 3/315:35 pm
MDW
- DEN
Nonstop2h 40m
Southwest
Deal found 2/3![Southwest logo]()
$191
This United Airlines deal was found by Cheapflights users on 2/6. 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 3/44:15 pm
DEN
- ORD
Nonstop2h 35m
United Airlines
Thu 3/510:05 pm
ORD
- DEN
Nonstop2h 51m
United Airlines
Deal found 2/6![United Airlines logo]()
$195
This Southwest deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/116:25 am
DEN
- MDW
Nonstop2h 25m
Southwest
Wed 3/185:55 am
MDW
- DEN
Nonstop2h 45m
Southwest
Deal found 2/4![Southwest logo]()
$191
This United Airlines deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/33:20 pm
DEN
- ORD
Nonstop2h 35m
United Airlines
Fri 3/69:39 pm
ORD
- DEN
Nonstop2h 51m
United Airlines
Deal found 2/4![United Airlines logo]()
$198
This Alaska Airlines deal was found by Cheapflights users on 2/6. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/1211:48 am
JAC
- ORD
1 stop11h 11m
Alaska Airlines
Fri 3/137:00 am
ORD
- JAC
1 stop29h 08m
Alaska Airlines
Deal found 2/6![Alaska Airlines logo]()
$265
This Kiwi.com deal was found by Cheapflights users on 2/6. 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 3/1310:40 pm
SLC
- ORD
1 stop16h 19m
Frontier
Mon 3/168:55 pm
ORD
- SLC
1 stop13h 15m
Frontier
Deal found 2/6![Frontier logo]()
$302
This Southwest deal was found by Cheapflights users on 2/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/285:55 am
DEN
- MDW
Nonstop2h 25m
Southwest
Wed 4/18:50 pm
MDW
- DEN
Nonstop2h 45m
Southwest
Deal found 2/5![Southwest logo]()
$191
This American Airlines deal was found by Cheapflights users on 2/5. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/1212:28 pm
JAC
- ORD
1 stop10h 19m
American Airlines
Fri 3/209:54 am
ORD
- JAC
Nonstop3h 24m
American Airlines
Deal found 2/5![American Airlines logo]()
$335
This Southwest deal was found by Cheapflights users on 2/6. 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 4/216:35 am
DEN
- MDW
Nonstop2h 20m
Southwest
Wed 4/2212:35 pm
MDW
- DEN
Nonstop2h 35m
Southwest
Deal found 2/6![Southwest logo]()
$195
This Delta deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/221:00 pm
JAC
- ORD
1 stop7h 18m
Delta
Sun 4/262:09 pm
ORD
- JAC
1 stop5h 52m
Delta
Deal found 2/3![Delta logo]()
$331
This Southwest deal was found by Cheapflights users on 2/6. 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.
Fri 4/248:20 pm
DEN
- MDW
Nonstop2h 20m
Southwest
Sun 4/266:00 am
MDW
- DEN
Nonstop2h 40m
Southwest
Deal found 2/6![Southwest logo]()
$197
This American Airlines deal was found by Cheapflights users on 2/5. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/203:10 pm
JAC
- ORD
1 stop7h 26m
American Airlines
Tue 2/247:00 am
ORD
- JAC
1 stop6h 38m
American Airlines
Deal found 2/5![American Airlines logo]()
$359
This Delta deal was found by Cheapflights users on 2/6. 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.
Thu 4/165:10 pm
SLC
- ORD
Nonstop3h 08m
Delta
Tue 4/217:20 am
ORD
- SLC
Nonstop3h 42m
Delta
Deal found 2/6![Delta logo]()
$347
This Southwest deal was found by Cheapflights users on 2/4. 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.
Sat 2/287:20 am
DEN
- MDW
Nonstop2h 35m
Southwest
Sat 2/283:15 pm
MDW
- DEN
Nonstop2h 40m
Southwest
Deal found 2/4![Southwest logo]()
$199
Last-minute flights from Wyoming to ChicagoDiscover last-minute flight deals from Wyoming to Chicago. Data last updated February 7, 2026 and is based on user searches.
Discover last-minute flight deals from Wyoming to Chicago. Data last updated February 7, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 2/4. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/2412:59 am
DEN
- ORD
1 stop8h 52m
Frontier
Sat 2/288:05 am
ORD
- DEN
1 stop25h 15m
Frontier
Deal found 2/4![Frontier logo]()
$127
This Cheapflightsfares deal was found by Cheapflights users on 2/4. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/267:35 pm
DEN
- ORD
Nonstop2h 39m
Frontier
Mon 3/27:35 am
ORD
- DEN
1 stop25h 51m
Frontier
Deal found 2/4![Frontier logo]()
$137
This Kiwi.com deal was found by Cheapflights users on 2/6. 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 2/279:41 am
DEN
- ORD
Nonstop2h 44m
Multiple Airlines
Tue 3/37:23 pm
ORD
- DEN
1 stop14h 48m
Multiple Airlines
Deal found 2/6![Multiple Airlines logo]()
$132
This Kiwi.com deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/279:41 am
DEN
- ORD
Nonstop2h 44m
Frontier
Mon 3/26:00 am
ORD
- DEN
1 stop26h 54m
Frontier
Deal found 2/4![Frontier logo]()
$134
This Kiwi.com deal was found by Cheapflights users on 2/4. 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 3/312:59 am
DEN
- MDW
1 stop17h 08m
Frontier
Wed 3/116:05 am
MDW
- DEN
1 stop17h 59m
Frontier
Deal found 2/4![Frontier logo]()
$139
This Cheapflightsfares deal was found by Cheapflights users on 2/4. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/43:36 pm
DEN
- ORD
1 stop21h 29m
Frontier
Wed 3/117:39 pm
ORD
- DEN
1 stop29h 51m
Frontier
Deal found 2/4![Frontier logo]()
$143
This Cheapflightsfares deal was found by Cheapflights users on 2/4. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/57:35 pm
DEN
- ORD
Nonstop2h 39m
Frontier
Thu 3/1210:53 am
ORD
- DEN
Nonstop2h 59m
Frontier
Deal found 2/4![Frontier logo]()
$131
This Cheapflightsfares deal was found by Cheapflights users on 2/4. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/57:35 pm
DEN
- ORD
Nonstop2h 39m
Frontier
Wed 3/117:39 pm
ORD
- DEN
1 stop15h 05m
Frontier
Deal found 2/4![Frontier logo]()
$133
This Kiwi.com deal was found by Cheapflights users on 2/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/611:59 pm
DEN
- ORD
1 stop10h 17m
Frontier
Fri 3/136:20 pm
ORD
- DEN
Nonstop3h 04m
Frontier
Deal found 2/5![Frontier logo]()
$139
This Cheapflightsfares deal was found by Cheapflights users on 2/7. 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.
Fri 3/69:19 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Mon 3/98:55 pm
ORD
- DEN
1 stop13h 06m
Frontier
Deal found 2/7![Frontier logo]()
$142
This Kiwi.com deal was found by Cheapflights users on 2/7. 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.
Sat 3/710:20 am
DEN
- ORD
1 stop13h 01m
Frontier
Tue 3/104:28 pm
ORD
- DEN
1 stop15h 45m
Frontier
Deal found 2/7![Frontier logo]()
$135
This Super.com deal was found by Cheapflights users on 2/6. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/99:19 pm
DEN
- ORD
Nonstop2h 38m
Frontier
Thu 3/1210:53 am
ORD
- DEN
Nonstop2h 59m
Frontier
Deal found 2/6![Frontier logo]()
$136
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 February 7, 2026.
Search for one-way flight options from Wyoming to Chicago. Find affordable one-way fares based on user searches. Data last updated February 7, 2026.
This Frontier deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/206:15 am
DEN
- ORD
Nonstop2h 35m
Frontier
Deal found 2/4![Frontier logo]()
$84
This Kiwi.com deal was found by Cheapflights users on 2/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/711:49 pm
DEN
- MDW
1 stop20h 30m
Frontier
Deal found 2/5![Frontier logo]()
$84
This Cheapflightsfares deal was found by Cheapflights users on 2/7. 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.
Thu 2/267:35 pm
DEN
- ORD
Nonstop2h 39m
Frontier
Deal found 2/7![Frontier logo]()
$85
This Kiwi.com deal was found by Cheapflights users on 2/7. 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.
Sun 3/811:59 pm
DEN
- MDW
1 stop18h 48m
Frontier
Deal found 2/7![Frontier logo]()
$85
This Cheapflightsfares deal was found by Cheapflights users on 2/6. 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 5/191:35 pm
DEN
- ORD
1 stop15h 15m
Frontier
Deal found 2/6![Frontier logo]()
$86
This Frontier deal was found by Cheapflights users on 2/7. 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.
Tue 3/3110:20 am
DEN
- MDW
1 stop9h 34m
Frontier
Deal found 2/7![Frontier logo]()
$86
This Flightnetwork deal was found by Cheapflights users on 2/4. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/218:24 pm
DEN
- ORD
1 stop10h 10m
Frontier
Deal found 2/4![Frontier logo]()
$87
This Kiwi.com deal was found by Cheapflights users on 2/6. 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.
Thu 3/56:00 am
DEN
- MDW
1 stop16h 51m
Frontier
Deal found 2/6![Frontier logo]()
$87
This Cheapflightsfares deal was found by Cheapflights users on 2/6. 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.
Fri 5/86:15 am
DEN
- ORD
Nonstop2h 35m
Frontier
Deal found 2/6![Frontier logo]()
$88
This Kiwi.com deal was found by Cheapflights users on 2/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/284:10 pm
DEN
- ORD
1 stop6h 07m
Frontier
Deal found 2/5![Frontier logo]()
$89
This Kiwi.com deal was found by Cheapflights users on 2/7. 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 3/2412:54 pm
DEN
- MDW
1 stop20h 31m
Frontier
Deal found 2/7![Frontier logo]()
$89
This Kiwi.com deal was found by Cheapflights users on 2/7. 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.
Wed 4/87:43 pm
DEN
- MDW
1 stop26h 30m
Frontier
Deal found 2/7![Frontier logo]()
$90
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 February 7, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $127 (Cheapflightsfares) |
One-way from | $84 (Frontier) |
Popular in | January |
Cheapest in | September |
Average price | $359 |
Good round-trip deal | $423 or less |
Good one-way deal | $305 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 February 7, 2026.
Use the filters below to find and compare flights from Wyoming to Chicago that are best for you.
Fly from
Wyoming
Fly to
Chicago
Route
Depart
Return
Price
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Tue 3/3
4:35 pm-7:55 pm
Nonstop2h 20m
Chicago Midway
Sat 3/7
9:35 pm-11:15 pm
Nonstop2h 40m
$179
Salt Lake CityChicago
SLC - MDW
SLCMDW
Salt Lake City
Mon 3/9
8:38 am-11:20 pm
1 stop13h 42m
Chicago Midway
Wed 3/11
11:25 am-12:14 am
2 stops13h 49m
$179
DenverChicago
DEN - ORD
DENORD
Denver Intl
Sat 3/7
2:45 pm-11:55 pm
1 stop8h 10m
Chicago O'Hare Intl
Sat 3/14
3:45 pm-11:50 pm
1 stop9h 05m
$182
DenverChicago
DEN - ORD
DENORD
Denver Intl
Sat 3/7
2:45 pm-11:55 pm
1 stop8h 10m
Chicago O'Hare Intl
Tue 3/10
4:50 pm-6:35 pm
Nonstop2h 45m
$189
DenverChicago
DEN - ORD
DENORD
Denver Intl
Sat 4/18
10:50 am-2:20 pm
Nonstop2h 30m
Chicago O'Hare Intl
Wed 4/22
10:30 am-12:15 pm
Nonstop2h 45m
$190
DenverChicago
DEN - ORD
DENORD
Denver Intl
Thu 3/26
6:00 am-9:38 am
Nonstop2h 38m
Chicago O'Hare Intl
Tue 3/31
5:45 pm-7:40 pm
Nonstop2h 55m
$191
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Thu 3/26
6:50 pm-10:05 pm
Nonstop2h 15m
Chicago Midway
Tue 3/31
5:35 pm-7:15 pm
Nonstop2h 40m
$191
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Wed 3/11
6:25 am-9:50 am
Nonstop2h 25m
Chicago Midway
Wed 3/18
5:55 am-7:40 am
Nonstop2h 45m
$191
DenverChicago
DEN - MDW
DENMDW
Denver Intl
Sat 3/28
5:55 am-9:20 am
Nonstop2h 25m
Chicago Midway
Wed 4/1
8:50 pm-10:35 pm
Nonstop2h 45m
$191
DenverChicago
DEN - ORD
DENORD
Denver Intl
Sat 5/16
9:20 pm-12:58 am
Nonstop2h 38m
Chicago O'Hare Intl
Tue 5/19
9:34 pm-11:30 pm
Nonstop2h 56m
$192
Showing 1-10 of 60 results
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
SLC-MDW
DEN-ORD
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-MDW
SLC-MDW
DEN-ORD
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 February 7, 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.
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
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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 February 7, 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 February 7, 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 February 7, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$191 | Average$385 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$289 | Average$407 | FlexibilityNo cancel fee | On-time69% |