$93+ Cheap flights from Wisconsin 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 12/24. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — CHI
Dec 10 — Dec 171
Round-trip
1 adult, Economy
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Find cheap flights from Wisconsin 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 Wisconsin to ChicagoExplore the most affordable flight options available from Wisconsin to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 10, 2026.
Explore the most affordable flight options available from Wisconsin to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 10, 2026.
This United Airlines deal was found by Cheapflights users on 11/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/72:21 pm -
Nonstop1h 39m
Mon 12/1410:25 am -
Nonstop1h 28m
Deal found 11/9![United Airlines logo]()
$180
This United Airlines deal was found by Cheapflights users on 11/5. 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.
Thu 11/265:05 am -
Nonstop1h 38m
Sun 11/2910:10 pm -
Nonstop1h 21m
Deal found 11/5![United Airlines logo]()
$201
This Southwest deal was found by Cheapflights users on 11/5. 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.
Thu 12/34:15 pm -
Nonstop0h 55m
Mon 12/79:10 pm -
Nonstop1h 05m
Deal found 11/5![Southwest logo]()
$209
This American Airlines deal was found by Cheapflights users on 11/7. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/52:57 pm -
Nonstop1h 21m
Sat 12/121:20 pm -
Nonstop1h 07m
Deal found 11/7![American Airlines logo]()
$231
This American Airlines deal was found by Cheapflights users on 11/8. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/57:40 am -
Nonstop1h 27m
Mon 12/710:05 am -
Nonstop1h 12m
Deal found 11/8![American Airlines logo]()
$244
This Southwest deal was found by Cheapflights users on 11/5. 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.
Mon 12/215:45 am -
Nonstop1h 00m
Mon 12/2810:00 am -
Nonstop0h 50m
Deal found 11/5![Southwest logo]()
$244
This United Airlines deal was found by Cheapflights users on 11/8. 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.
Sat 12/55:00 am -
Nonstop1h 10m
Mon 12/78:52 am -
Nonstop1h 11m
Deal found 11/8![United Airlines logo]()
$246
This Southwest deal was found by Cheapflights users on 11/8. 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.
Sat 12/51:45 pm -
Nonstop0h 55m
Mon 12/710:10 am -
Nonstop0h 50m
Deal found 11/8![Southwest logo]()
$246
This American Airlines deal was found by Cheapflights users on 11/5. 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.
Sun 12/68:12 pm -
Nonstop1h 21m
Sun 12/135:29 pm -
Nonstop1h 14m
Deal found 11/5![American Airlines logo]()
$249
This Southwest deal was found by Cheapflights users on 11/5. 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.
Sun 12/65:30 am -
Nonstop1h 05m
Sun 12/1310:10 am -
Nonstop0h 50m
Deal found 11/5![Southwest logo]()
$249
This United Airlines deal was found by Cheapflights users on 11/8. 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 12/232:31 pm -
Nonstop1h 14m
Sat 12/264:40 pm -
Nonstop1h 11m
Deal found 11/8![United Airlines logo]()
$255
This United Airlines deal was found by Cheapflights users on 11/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/75:00 am -
Nonstop1h 10m
Mon 12/144:15 pm -
Nonstop1h 03m
Deal found 11/9![United Airlines logo]()
$261
Best flights from Wisconsin to ChicagoDiscover carefully curated flight deals from Wisconsin to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated November 10, 2026.
Discover carefully curated flight deals from Wisconsin to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated November 10, 2026.
This United Airlines deal was found by Cheapflights users on 11/6. 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.
Fri 5/72:45 pm -
Nonstop1h 33m
Sat 5/1512:35 pm -
Nonstop1h 30m
Deal found 11/6![United Airlines logo]()
$180
This Southwest deal was found by Cheapflights users on 11/5. 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.
Thu 12/38:00 am -
1 stop4h 05m
Mon 12/75:25 pm -
1 stop4h 55m
Deal found 11/5![Southwest logo]()
$229
This Delta deal was found by Cheapflights users on 11/6. 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.
Wed 12/1612:30 pm -
1 stop4h 13m
Fri 3/266:00 am -
1 stop5h 42m
Deal found 11/6![Delta logo]()
$265
This American Airlines deal was found by Cheapflights users on 11/8. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/1610:05 am -
Nonstop1h 25m
Sun 4/188:11 am -
Nonstop1h 24m
Deal found 11/8![American Airlines logo]()
$309
This United Airlines deal was found by Cheapflights users on 11/8. 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.
Tue 1/195:15 am -
Nonstop1h 44m
Tue 1/2610:00 pm -
Nonstop1h 35m
Deal found 11/8![United Airlines logo]()
$180
This United Airlines deal was found by Cheapflights users on 11/5. 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 1/265:15 am -
Nonstop1h 44m
Tue 2/910:00 pm -
Nonstop1h 35m
Deal found 11/5![United Airlines logo]()
$180
This United Airlines deal was found by Cheapflights users on 11/8. 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 1/62:20 pm -
Nonstop1h 37m
Sun 1/1011:29 am -
Nonstop1h 39m
Deal found 11/8![United Airlines logo]()
$180
This United Airlines deal was found by Cheapflights users on 11/6. 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 12/125:51 am -
Nonstop1h 39m
Mon 12/1410:09 pm -
Nonstop1h 21m
Deal found 11/6![United Airlines logo]()
$180
This Southwest deal was found by Cheapflights users on 11/5. 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.
Mon 12/215:45 am -
Nonstop1h 00m
Mon 12/2810:00 am -
Nonstop0h 50m
Deal found 11/5![Southwest logo]()
$244
This Southwest deal was found by Cheapflights users on 11/5. 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.
Sun 12/65:30 am -
Nonstop1h 05m
Sun 12/1310:10 am -
Nonstop0h 50m
Deal found 11/5![Southwest logo]()
$249
This Delta deal was found by Cheapflights users on 11/4. 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.
Sun 12/206:31 am -
1 stop5h 22m
Sun 12/276:29 am -
1 stop5h 21m
Deal found 11/4![Delta logo]()
$275
This United Airlines deal was found by Cheapflights users on 11/6. 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 1/255:15 am -
Nonstop1h 44m
Fri 1/2911:29 am -
Nonstop1h 39m
Deal found 11/6![United Airlines logo]()
$200
This American Airlines deal was found by Cheapflights users on 11/6. 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.
Thu 12/246:01 am -
Nonstop1h 40m
Thu 12/315:00 pm -
Nonstop1h 31m
Deal found 11/6![American Airlines logo]()
$309
This Southwest deal was found by Cheapflights users on 11/9. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/76:20 am -
Nonstop1h 00m
Mon 12/149:10 pm -
Nonstop1h 05m
Deal found 11/9![Southwest logo]()
$261
This American Airlines deal was found by Cheapflights users on 11/9. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/115:55 am -
Nonstop1h 35m
Sun 12/1310:05 am -
Nonstop1h 34m
Deal found 11/9![American Airlines logo]()
$309
This Southwest deal was found by Cheapflights users on 11/8. 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.
Sat 12/57:20 am -
1 stop8h 15m
Mon 12/711:45 am -
1 stop3h 30m
Deal found 11/8![Southwest logo]()
$271
This United Airlines deal was found by Cheapflights users on 11/8. 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.
Tue 1/129:20 am -
Nonstop1h 20m
Tue 1/123:35 pm -
Nonstop1h 11m
Deal found 11/8![United Airlines logo]()
$231
This Delta deal was found by Cheapflights users on 11/9. 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.
Thu 12/247:00 am -
1 stop5h 46m
Wed 12/3010:30 am -
1 stop6h 04m
Deal found 11/9![Delta logo]()
$339
This American Airlines deal was found by Cheapflights users on 11/5. 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 1/155:34 am -
Nonstop1h 41m
Sat 1/2310:25 pm -
Nonstop1h 29m
Deal found 11/5![American Airlines logo]()
$309
This Delta deal was found by Cheapflights users on 11/9. 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 12/155:39 pm -
1 stop3h 56m
Sat 12/196:29 am -
1 stop5h 27m
Deal found 11/9![Delta logo]()
$339
This American Airlines deal was found by Cheapflights users on 11/5. 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.
Sun 1/108:32 pm -
Nonstop1h 33m
Sun 1/1710:25 pm -
Nonstop1h 29m
Deal found 11/5![American Airlines logo]()
$309
This United Airlines deal was found by Cheapflights users on 11/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/18:00 am -
Nonstop1h 44m
Sat 1/910:00 pm -
Nonstop1h 35m
Deal found 11/9![United Airlines logo]()
$238
This Mytrip deal was found by Cheapflights users on 11/6. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/212:11 pm -
2 stops29h 19m
Mon 12/281:11 pm -
3 stops24h 56m
Deal found 11/6![Multiple Airlines logo]()
$896
This Delta deal was found by Cheapflights users on 11/8. 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.
Sat 12/511:20 am -
1 stop4h 57m
Mon 12/72:41 pm -
1 stop6h 15m
Deal found 11/8![Delta logo]()
$339
This American Airlines deal was found by Cheapflights users on 11/7. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/155:34 am -
Nonstop1h 41m
Sun 1/179:26 am -
Nonstop1h 31m
Deal found 11/7![American Airlines logo]()
$309
This United Airlines deal was found by Cheapflights users on 11/5. 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.
Wed 12/308:20 am -
Nonstop1h 20m
Sun 1/34:40 pm -
Nonstop1h 11m
Deal found 11/5![United Airlines logo]()
$244
This Delta deal was found by Cheapflights users on 11/9. 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.
Fri 1/86:40 am -
1 stop6h 16m
Sun 1/1010:33 am -
1 stop6h 11m
Deal found 11/9![Delta logo]()
$339
This American Airlines deal was found by Cheapflights users on 11/8. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/58:32 pm -
Nonstop1h 33m
Fri 2/195:26 pm -
Nonstop1h 26m
Deal found 11/8![American Airlines logo]()
$309
This United Airlines deal was found by Cheapflights users on 11/8. 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.
Sat 12/55:00 am -
Nonstop1h 10m
Mon 12/78:52 am -
Nonstop1h 11m
Deal found 11/8![United Airlines logo]()
$246
This Delta deal was found by Cheapflights users on 11/8. 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.
Fri 12/1111:20 am -
1 stop4h 57m
Sun 12/135:02 pm -
1 stop3h 54m
Deal found 11/8![Delta logo]()
$339
Last-minute flights from Wisconsin to ChicagoDiscover last-minute flight deals from Wisconsin to Chicago. Data last updated November 10, 2026 and is based on user searches.
Discover last-minute flight deals from Wisconsin to Chicago. Data last updated November 10, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 11/5. 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.
Thu 11/265:05 am -
Nonstop1h 38m
Sun 11/2910:10 pm -
Nonstop1h 21m
Deal found 11/5![United Airlines logo]()
$201
This Southwest deal was found by Cheapflights users on 11/5. 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.
Thu 12/34:15 pm -
Nonstop0h 55m
Mon 12/79:10 pm -
Nonstop1h 05m
Deal found 11/5![Southwest logo]()
$209
This American Airlines deal was found by Cheapflights users on 11/7. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/52:57 pm -
Nonstop1h 21m
Sat 12/121:20 pm -
Nonstop1h 07m
Deal found 11/7![American Airlines logo]()
$231
This American Airlines deal was found by Cheapflights users on 11/8. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/57:40 am -
Nonstop1h 27m
Mon 12/710:05 am -
Nonstop1h 12m
Deal found 11/8![American Airlines logo]()
$244
This United Airlines deal was found by Cheapflights users on 11/8. 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.
Sat 12/55:00 am -
Nonstop1h 10m
Mon 12/78:52 am -
Nonstop1h 11m
Deal found 11/8![United Airlines logo]()
$246
This Southwest deal was found by Cheapflights users on 11/8. 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.
Sat 12/51:45 pm -
Nonstop0h 55m
Mon 12/710:10 am -
Nonstop0h 50m
Deal found 11/8![Southwest logo]()
$246
This American Airlines deal was found by Cheapflights users on 11/5. 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.
Sun 12/68:12 pm -
Nonstop1h 21m
Sun 12/135:29 pm -
Nonstop1h 14m
Deal found 11/5![American Airlines logo]()
$249
This Southwest deal was found by Cheapflights users on 11/5. 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.
Sun 12/65:30 am -
Nonstop1h 05m
Sun 12/1310:10 am -
Nonstop0h 50m
Deal found 11/5![Southwest logo]()
$249
This United Airlines deal was found by Cheapflights users on 11/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/72:21 pm -
Nonstop1h 39m
Mon 12/1410:25 am -
Nonstop1h 28m
Deal found 11/9![United Airlines logo]()
$180
This United Airlines deal was found by Cheapflights users on 11/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/75:00 am -
Nonstop1h 10m
Mon 12/144:15 pm -
Nonstop1h 03m
Deal found 11/9![United Airlines logo]()
$261
This Southwest deal was found by Cheapflights users on 11/5. 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.
Mon 12/215:45 am -
Nonstop1h 00m
Mon 12/2810:00 am -
Nonstop0h 50m
Deal found 11/5![Southwest logo]()
$244
This United Airlines deal was found by Cheapflights users on 11/8. 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 12/232:31 pm -
Nonstop1h 14m
Sat 12/264:40 pm -
Nonstop1h 11m
Deal found 11/8![United Airlines logo]()
$255
One-way flights from Wisconsin to ChicagoSearch for one-way flight options from Wisconsin to Chicago. Find affordable one-way fares based on user searches. Data last updated November 10, 2026.
Search for one-way flight options from Wisconsin to Chicago. Find affordable one-way fares based on user searches. Data last updated November 10, 2026.
This United Airlines deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” 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 12/245:01 am -
Nonstop1h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/10![United Airlines logo]()
$93
This deal was found by Cheapflights users on 11/9. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/35:30 am -
Nonstop1h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/9![United Airlines logo]()
$103
This United Airlines deal was found by Cheapflights users on 11/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/305:00 am -
Nonstop1h 19m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/9![United Airlines logo]()
$116
This American Airlines deal was found by Cheapflights users on 11/5. 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.
Sun 12/202:08 pm -
Nonstop1h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/5![American Airlines logo]()
$125
This Southwest deal was found by Cheapflights users on 11/5. 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.
Sun 12/205:20 pm -
Nonstop0h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/5![Southwest logo]()
$125
This American Airlines deal was found by Cheapflights users on 11/9. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/311:47 am -
Nonstop1h 23m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/9![American Airlines logo]()
$131
This Southwest deal was found by Cheapflights users on 11/9. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/36:20 am -
Nonstop1h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/9![Southwest logo]()
$131
This United Airlines deal was found by Cheapflights users on 11/7. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/55:15 am -
Nonstop1h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/7![United Airlines logo]()
$132
This United Airlines deal was found by Cheapflights users on 11/6. 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.
Sun 12/137:17 pm -
Nonstop1h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/6![United Airlines logo]()
$140
This Southwest deal was found by Cheapflights users on 11/6. 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.
Sun 12/135:30 am -
Nonstop1h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/6![Southwest logo]()
$140
This United Airlines deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/1210:38 am -
Nonstop1h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/5![United Airlines logo]()
$150
This United Airlines deal was found by Cheapflights users on 11/5. 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.
Wed 11/255:05 am -
Nonstop1h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/5![United Airlines logo]()
$153
Find flight deals from Wisconsin to Chicago
Keep the following information in mind while searching for Wisconsin to Chicago flight deals. Data was last updated November 10, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $180 (United Airlines) |
One-way from | $93 (United Airlines) |
Good round-trip deal | $258 or less |
Good one-way deal | $219 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Wisconsin 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 November 10, 2026.
Use the filters below to find and compare flights from Wisconsin to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Eau ClaireChicago
EAU Eau Claire - ORD Chicago O'Hare Intl
EAUORD
Eau Claire
Fri 12/25
8:00 am-9:44 am
Nonstop1h 44m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$93
Eau ClaireChicago
EAU Eau Claire - ORD Chicago O'Hare Intl
EAUORD
Eau Claire
Sat 4/3
5:30 am-7:05 am
Nonstop1h 35m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$103
Eau ClaireChicago
EAU Eau Claire - ORD Chicago O'Hare Intl
EAUORD
Eau Claire
Sun 4/4
2:45 pm-4:18 pm
Nonstop1h 33m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$103
MilwaukeeChicago
MKE Milwaukee-Mitchell - ORD Chicago O'Hare Intl
MKEORD
Milwaukee-Mitchell
Wed 12/23
7:33 am-9:00 am
Nonstop1h 27m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$116
MilwaukeeChicago
MKE Milwaukee-Mitchell - ORD Chicago O'Hare Intl
MKEORD
Milwaukee-Mitchell
Tue 1/19
6:50 pm-8:11 pm
Nonstop1h 21m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$116
MilwaukeeChicago
MKE Milwaukee-Mitchell - ORD Chicago O'Hare Intl
MKEORD
Milwaukee-Mitchell
Wed 12/30
5:00 am-6:19 am
Nonstop1h 19m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$116
MilwaukeeChicago
MKE Milwaukee-Mitchell - ORD Chicago O'Hare Intl
MKEORD
Milwaukee-Mitchell
Tue 12/29
10:38 am-11:58 am
Nonstop1h 20m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$116
MilwaukeeChicago
MKE Milwaukee-Mitchell - ORD Chicago O'Hare Intl
MKEORD
Milwaukee-Mitchell
Tue 1/12
3:51 pm-5:05 pm
Nonstop1h 14m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$116
Quickest round-trip
MilwaukeeChicago
MKE Milwaukee-Mitchell - MDW Chicago Midway
MKEMDW
Milwaukee-Mitchell
Mon 12/7
4:20 pm-5:15 pm
Nonstop0h 55m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$131
MilwaukeeChicago
MKE Milwaukee-Mitchell - MDW Chicago Midway
MKEMDW
Milwaukee-Mitchell
Thu 12/3
6:20 am-7:20 am
Nonstop1h 00m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$131
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Wisconsin to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Wisconsin with our price prediction graph.
EAU-ORD
MKE-ORD
MKE-MDW
MSN-MDW
ATW-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 Wisconsin to Chicago
USWI-CHI
EAU-ORD
MKE-ORD
MKE-MDW
MSN-MDW
What is the cheapest month to book a flight from Wisconsin to Chicago?
Currently, December is the cheapest month in which you can book a flight from Wisconsin to Chicago (average of $239). Flying from Wisconsin to Chicago in October is currently the most expensive (average of $399). 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 WI to CHI?
Find hourly flight availability from Wisconsin 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 November 10, 2026.
One of the essential ways to save on airfare from Wisconsin to Chicago is to remain as flexible as possible. Flights that are in the evening tend to be the most expensive. A flight in the morning could potentially save you up to 28% on airfare.
Weekly flight availability from Wisconsin to Chicago
Explore weekly flight availability from Wisconsin 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 November 10, 2026.
The most flights from USWI to CHI are scheduled on a Sunday (56 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (43 on average).
What is the cheapest day to fly from Wisconsin to Chicago?
Use this chart to determine the cheapest time to fly round-trip from Wisconsin to Chicago. Price data was last updated on November 7, 2026.
Travelers seeking maximum savings on their Wisconsin to Chicago flight should consider departing on Thursday afternoons when fares are most often at their lowest. Saturday evenings flights should be avoided if possible as fares are typically the most expensive at this time.
Related info for your journey
Find useful and relevant information for your journey from Wisconsin 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
Merrillville
Lansing
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 Wisconsin 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 November 10, 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 Wisconsin to Chicago by cabin class
Find flights from Wisconsin to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Wisconsin and Chicago flights
Browse other Wisconsin and Chicago flight options. Last updated on November 10, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Wisconsin to Chicago flights
Consider these flights traveling from Wisconsin to Chicago.
Top 2 airlines flying from Wisconsin to Chicago
Discover the top 2 airlines that operate flights from Wisconsin 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 November 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$171 | Average$280 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$179 | Average$334 | FlexibilityNo cancel fee | On-time71% |