$116+ Cheap flights from Oshkosh, WI 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 8/24. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — CHI
Jul 30 — Aug 61
Round-trip
1 adult, Economy
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Cheapest flights from Oshkosh to ChicagoExplore the most affordable flight options available from Oshkosh to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 30, 2026.
Explore the most affordable flight options available from Oshkosh to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 30, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” 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 8/244:04 pm
ATW
- ORD
1 stop20h 46m
Multiple Airlines
Wed 9/164:49 pm
ORD
- ATW
1 stop30h 16m
Multiple Airlines
Deal found 6/28![Multiple Airlines logo]()
$235
This United Airlines deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” 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 7/302:39 pm
ATW
- ORD
Nonstop1h 20m
United Airlines
Sat 8/112:45 pm
ORD
- ATW
Nonstop1h 20m
United Airlines
Deal found 6/25![United Airlines logo]()
$239
This American Airlines deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” 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 9/2511:36 am
ATW
- ORD
Nonstop1h 23m
American Airlines
Sat 10/1011:00 pm
ORD
- ATW
Nonstop1h 12m
American Airlines
Deal found 6/28![American Airlines logo]()
$254
This Delta deal was found by Cheapflights users on 6/26. Clicking the “Pick Dates” 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 7/302:05 pm
ATW
- ORD
1 stop4h 24m
Delta
Tue 8/46:00 am
ORD
- ATW
1 stop4h 20m
Delta
Deal found 6/26![Delta logo]()
$259
This American Airlines deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” 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 7/107:15 pm
ATW
- ORD
Nonstop1h 40m
American Airlines
Tue 7/145:03 pm
ORD
- ATW
Nonstop1h 15m
American Airlines
Deal found 6/25![American Airlines logo]()
$269
This Delta deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” 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 7/152:05 pm
ATW
- ORD
1 stop4h 24m
Delta
Wed 7/296:30 am
ORD
- ATW
1 stop4h 17m
Delta
Deal found 6/29![Delta logo]()
$274
This United Airlines deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” 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 7/23:44 pm
ATW
- ORD
Nonstop1h 21m
United Airlines
Thu 7/96:00 pm
ORD
- ATW
Nonstop1h 22m
United Airlines
Deal found 6/25![United Airlines logo]()
$284
This Delta deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” 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 7/1011:27 am
ATW
- MDW
1 stop6h 51m
Delta
Tue 7/141:18 pm
MDW
- ATW
1 stop4h 32m
Delta
Deal found 6/25![Delta logo]()
$289
This Delta deal was found by Cheapflights users on 6/26. Clicking the “Pick Dates” 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 7/114:10 pm
ATW
- ORD
1 stop5h 42m
Delta
Wed 7/156:30 am
ORD
- ATW
1 stop4h 17m
Delta
Deal found 6/26![Delta logo]()
$289
This American Airlines deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” 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 12/126:02 am
ATW
- ORD
Nonstop1h 28m
American Airlines
Wed 12/234:15 pm
ORD
- ATW
Nonstop1h 20m
American Airlines
Deal found 6/30![American Airlines logo]()
$298
This United Airlines deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” 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 7/95:29 pm
ATW
- ORD
Nonstop1h 30m
United Airlines
Sun 7/123:35 pm
ORD
- ATW
Nonstop1h 19m
United Airlines
Deal found 6/29![United Airlines logo]()
$299
This Delta deal was found by Cheapflights users on 6/27. Clicking the “Pick Dates” 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 7/77:00 am
ATW
- MDW
1 stop5h 38m
Delta
Sat 7/116:55 pm
MDW
- ATW
1 stop4h 01m
Delta
Deal found 6/27![Delta logo]()
$304
Best flights from Oshkosh to ChicagoDiscover carefully curated flight deals from Oshkosh to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 30, 2026.
Discover carefully curated flight deals from Oshkosh to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 30, 2026.
This United Airlines deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” 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 7/1510:37 am
ATW
- ORD
Nonstop1h 22m
United Airlines
Wed 7/291:55 pm
ORD
- ATW
Nonstop1h 14m
United Airlines
Deal found 6/29![United Airlines logo]()
$254
This Delta deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” 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 8/282:06 pm
ATW
- ORD
1 stop4h 23m
Delta
Thu 9/36:00 am
ORD
- ATW
1 stop4h 20m
Delta
Deal found 6/25![Delta logo]()
$259
This American Airlines deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” 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 7/107:15 pm
ATW
- ORD
Nonstop1h 40m
American Airlines
Tue 7/145:03 pm
ORD
- ATW
Nonstop1h 15m
American Airlines
Deal found 6/25![American Airlines logo]()
$269
This Kiwi.com deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” 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 9/911:00 am
ATW
- ORD
1 stop12h 55m
Multiple Airlines
Thu 9/104:49 pm
ORD
- ATW
1 stop28h 11m
Multiple Airlines
Deal found 6/29![Multiple Airlines logo]()
$322
This Delta deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” 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 9/2210:57 am
ATW
- ORD
1 stop6h 36m
Delta
Sat 10/36:24 pm
ORD
- ATW
1 stop4h 38m
Delta
Deal found 6/29![Delta logo]()
$259
This United Airlines deal was found by Cheapflights users on 6/26. Clicking the “Pick Dates” 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 7/112:40 pm
ATW
- ORD
Nonstop1h 20m
United Airlines
Wed 7/1510:25 am
ORD
- ATW
Nonstop1h 18m
United Airlines
Deal found 6/26![United Airlines logo]()
$269
This Delta deal was found by Cheapflights users on 6/26. Clicking the “Pick Dates” 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 7/302:05 pm
ATW
- ORD
1 stop4h 24m
Delta
Tue 8/46:00 am
ORD
- ATW
1 stop4h 20m
Delta
Deal found 6/26![Delta logo]()
$259
This Delta deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” 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 7/302:05 pm
ATW
- ORD
1 stop4h 24m
Delta
Sun 8/26:30 am
ORD
- ATW
1 stop4h 17m
Delta
Deal found 6/28![Delta logo]()
$259
This Delta deal was found by Cheapflights users on 6/26. Clicking the “Pick Dates” 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 8/1911:00 am
ATW
- ORD
1 stop6h 41m
Delta
Wed 8/267:00 am
ORD
- ATW
1 stop3h 29m
Delta
Deal found 6/26![Delta logo]()
$259
This Delta deal was found by Cheapflights users on 6/27. Clicking the “Pick Dates” 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 8/177:00 am
ATW
- ORD
1 stop5h 54m
Delta
Sat 8/296:59 am
ORD
- ATW
1 stop3h 30m
Delta
Deal found 6/27![Delta logo]()
$259
This Delta deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” 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 7/1011:27 am
ATW
- MDW
1 stop6h 51m
Delta
Tue 7/141:18 pm
MDW
- ATW
1 stop4h 32m
Delta
Deal found 6/25![Delta logo]()
$289
This Delta deal was found by Cheapflights users on 6/26. Clicking the “Pick Dates” 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 7/114:10 pm
ATW
- ORD
1 stop5h 42m
Delta
Wed 7/156:30 am
ORD
- ATW
1 stop4h 17m
Delta
Deal found 6/26![Delta logo]()
$289
This Delta deal was found by Cheapflights users on 6/27. Clicking the “Pick Dates” 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 7/257:00 am
ATW
- ORD
1 stop6h 46m
Delta
Sat 8/111:10 am
ORD
- ATW
1 stop5h 28m
Delta
Deal found 6/27![Delta logo]()
$289
This Delta deal was found by Cheapflights users on 6/27. Clicking the “Pick Dates” 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 7/1111:27 am
ATW
- MDW
1 stop6h 25m
Delta
Mon 7/131:18 pm
MDW
- ATW
1 stop4h 32m
Delta
Deal found 6/27![Delta logo]()
$304
This Delta deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” 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 7/152:05 pm
ATW
- MDW
1 stop4h 20m
Delta
Wed 7/299:19 am
MDW
- ATW
1 stop4h 06m
Delta
Deal found 6/29![Delta logo]()
$304
This Delta deal was found by Cheapflights users on 6/27. Clicking the “Pick Dates” 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 7/1011:27 am
ATW
- MDW
1 stop6h 51m
Delta
Mon 7/131:18 pm
MDW
- ATW
1 stop4h 32m
Delta
Deal found 6/27![Delta logo]()
$319
This Delta deal was found by Cheapflights users on 6/27. Clicking the “Pick Dates” 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 7/1011:27 am
ATW
- MDW
1 stop6h 51m
Delta
Sun 7/129:19 am
MDW
- ATW
1 stop4h 06m
Delta
Deal found 6/27![Delta logo]()
$382
This Delta deal was found by Cheapflights users on 6/27. Clicking the “Pick Dates” 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 8/212:06 pm
ATW
- MDW
1 stop4h 27m
Delta
Sun 8/239:24 am
MDW
- ATW
1 stop12h 13m
Delta
Deal found 6/27![Delta logo]()
$441
This Delta deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” 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 7/302:05 pm
ATW
- MDW
1 stop4h 20m
Delta
Sun 8/29:19 am
MDW
- ATW
1 stop4h 06m
Delta
Deal found 6/28![Delta logo]()
$474
This Delta deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” 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 9/257:00 am
ATW
- MDW
1 stop5h 39m
Delta
Sat 10/105:21 pm
MDW
- ATW
1 stop4h 13m
Delta
Deal found 6/29![Delta logo]()
$479
This Delta deal was found by Cheapflights users on 6/26. Clicking the “Pick Dates” 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 12/1212:06 pm
ATW
- MDW
1 stop4h 44m
Delta
Wed 12/235:35 pm
MDW
- ATW
1 stop4h 00m
Delta
Deal found 6/26![Delta logo]()
$504
This Delta deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” 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 7/147:00 am
ATW
- MDW
1 stop5h 38m
Delta
Sat 7/189:54 am
MDW
- ATW
1 stop5h 36m
Delta
Deal found 6/28![Delta logo]()
$534
Last-minute flights from Oshkosh to ChicagoDiscover last-minute flight deals from Oshkosh to Chicago. Data last updated June 30, 2026 and is based on user searches.
Discover last-minute flight deals from Oshkosh to Chicago. Data last updated June 30, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” 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 7/23:44 pm
ATW
- ORD
Nonstop1h 21m
United Airlines
Thu 7/96:00 pm
ORD
- ATW
Nonstop1h 22m
United Airlines
Deal found 6/25![United Airlines logo]()
$284
This Delta deal was found by Cheapflights users on 6/26. Clicking the “Pick Dates” 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 7/37:00 am
ATW
- MDW
1 stop5h 46m
Delta
Fri 7/37:16 pm
MDW
- ATW
1 stop3h 42m
Delta
Deal found 6/26![Delta logo]()
$319
This Delta deal was found by Cheapflights users on 6/27. Clicking the “Pick Dates” 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 7/77:00 am
ATW
- MDW
1 stop5h 38m
Delta
Sat 7/116:55 pm
MDW
- ATW
1 stop4h 01m
Delta
Deal found 6/27![Delta logo]()
$304
This Delta deal was found by Cheapflights users on 6/27. Clicking the “Pick Dates” 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 7/77:00 am
ATW
- ORD
1 stop6h 03m
Delta
Wed 7/156:30 am
ORD
- ATW
1 stop4h 17m
Delta
Deal found 6/27![Delta logo]()
$304
This United Airlines deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” 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 7/95:29 pm
ATW
- ORD
Nonstop1h 30m
United Airlines
Thu 7/166:00 pm
ORD
- ATW
Nonstop1h 22m
United Airlines
Deal found 6/25![United Airlines logo]()
$254
This United Airlines deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” 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 7/95:29 pm
ATW
- ORD
Nonstop1h 30m
United Airlines
Sun 7/123:35 pm
ORD
- ATW
Nonstop1h 19m
United Airlines
Deal found 6/29![United Airlines logo]()
$299
This American Airlines deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” 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 7/107:15 pm
ATW
- ORD
Nonstop1h 40m
American Airlines
Tue 7/145:03 pm
ORD
- ATW
Nonstop1h 15m
American Airlines
Deal found 6/25![American Airlines logo]()
$269
This Delta deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” 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 7/1011:27 am
ATW
- MDW
1 stop6h 51m
Delta
Tue 7/141:18 pm
MDW
- ATW
1 stop4h 32m
Delta
Deal found 6/25![Delta logo]()
$289
This Delta deal was found by Cheapflights users on 6/26. Clicking the “Pick Dates” 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 7/114:10 pm
ATW
- ORD
1 stop5h 42m
Delta
Wed 7/156:30 am
ORD
- ATW
1 stop4h 17m
Delta
Deal found 6/26![Delta logo]()
$289
This Delta deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” 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 7/152:05 pm
ATW
- ORD
1 stop4h 24m
Delta
Wed 7/296:30 am
ORD
- ATW
1 stop4h 17m
Delta
Deal found 6/29![Delta logo]()
$274
This United Airlines deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” 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 7/302:39 pm
ATW
- ORD
Nonstop1h 20m
United Airlines
Sat 8/112:45 pm
ORD
- ATW
Nonstop1h 20m
United Airlines
Deal found 6/25![United Airlines logo]()
$239
This Delta deal was found by Cheapflights users on 6/26. Clicking the “Pick Dates” 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 7/302:05 pm
ATW
- ORD
1 stop4h 24m
Delta
Tue 8/46:00 am
ORD
- ATW
1 stop4h 20m
Delta
Deal found 6/26![Delta logo]()
$259
One-way flights from Oshkosh to ChicagoSearch for one-way flight options from Oshkosh to Chicago. Find affordable one-way fares based on user searches. Data last updated June 30, 2026.
Search for one-way flight options from Oshkosh to Chicago. Find affordable one-way fares based on user searches. Data last updated June 30, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” 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 8/244:04 pm
ATW
- ORD
1 stop20h 46m
Multiple Airlines
Deal found 6/28![Multiple Airlines logo]()
$116
This Kiwi.com deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” 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 7/279:36 am
ATW
- ORD
1 stop26h 39m
Multiple Airlines
Deal found 6/28![Multiple Airlines logo]()
$123
This Kiwi.com deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” 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 8/39:36 am
ATW
- ORD
1 stop26h 39m
Multiple Airlines
Deal found 6/29![Multiple Airlines logo]()
$126
This Kiwi.com deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” 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 8/284:04 pm
ATW
- ORD
1 stop20h 46m
Multiple Airlines
Deal found 6/29![Multiple Airlines logo]()
$127
This Kiwi.com deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” 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 8/304:17 pm
ATW
- ORD
1 stop30h 51m
Multiple Airlines
Deal found 6/29![Multiple Airlines logo]()
$129
This Kiwi.com deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” 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 7/209:36 am
ATW
- ORD
1 stop26h 39m
Multiple Airlines
Deal found 6/25![Multiple Airlines logo]()
$135
This Kiwi.com deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” 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 8/234:17 pm
ATW
- ORD
1 stop30h 51m
Multiple Airlines
Deal found 6/28![Multiple Airlines logo]()
$138
This Kiwi.com deal was found by Cheapflights users on 6/26. Clicking the “Pick Dates” 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 9/244:10 pm
ATW
- ORD
1 stop7h 45m
Multiple Airlines
Deal found 6/26![Multiple Airlines logo]()
$147
This Kiwi.com deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” 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 8/39:36 am
ATW
- MDW
2 stops25h 31m
Multiple Airlines
Deal found 6/29![Multiple Airlines logo]()
$207
This Kiwi.com deal was found by Cheapflights users on 6/27. Clicking the “Pick Dates” 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 7/302:44 pm
ATW
- MDW
2 stops31h 19m
Multiple Airlines
Deal found 6/27![Multiple Airlines logo]()
$212
This Delta deal was found by Cheapflights users on 6/27. Clicking the “Pick Dates” 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 7/302:05 pm
ATW
- MDW
1 stop4h 20m
Delta
Deal found 6/27![Delta logo]()
$244
This Delta deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” 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 7/1111:27 am
ATW
- MDW
1 stop6h 25m
Delta
Deal found 6/25![Delta logo]()
$319
Find flight deals from Oshkosh to Chicago
Keep the following information in mind while searching for Oshkosh to Chicago flight deals. Data was last updated June 30, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $235 (Kiwi.com) |
One-way from | $116 (Kiwi.com) |
Popular in | September |
Cheapest in | February |
Cheapflights Fare Finder
Customize your flight search to find flights from Oshkosh 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 30, 2026.
Use the filters below to find and compare flights from Oshkosh to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
AppletonChicago
ATW - ORD
ATWORD
Appleton Intl
Wed 7/15
10:37 am-11:59 am
Nonstop1h 22m
Chicago O'Hare Intl
Wed 7/29
1:55 pm-3:09 pm
Nonstop1h 14m
$254
AppletonChicago
ATW - ORD
ATWORD
Appleton Intl
Fri 8/28
2:06 pm-6:29 pm
1 stop4h 23m
Chicago O'Hare Intl
Thu 9/3
6:00 am-10:20 am
1 stop4h 20m
$259
AppletonChicago
ATW - ORD
ATWORD
Appleton Intl
Tue 9/22
10:57 am-5:33 pm
1 stop6h 36m
Chicago O'Hare Intl
Sat 10/3
6:24 pm-11:02 pm
1 stop4h 38m
$259
AppletonChicago
ATW - ORD
ATWORD
Appleton Intl
Thu 7/30
2:05 pm-6:29 pm
1 stop4h 24m
Chicago O'Hare Intl
Tue 8/4
6:00 am-10:20 am
1 stop4h 20m
$259
AppletonChicago
ATW - ORD
ATWORD
Appleton Intl
Thu 7/30
2:05 pm-6:29 pm
1 stop4h 24m
Chicago O'Hare Intl
Sun 8/2
6:30 am-10:47 am
1 stop4h 17m
$259
AppletonChicago
ATW - ORD
ATWORD
Appleton Intl
Wed 8/19
11:00 am-5:41 pm
1 stop6h 41m
Chicago O'Hare Intl
Wed 8/26
7:00 am-10:29 am
1 stop3h 29m
$259
AppletonChicago
ATW - ORD
ATWORD
Appleton Intl
Mon 8/17
7:00 am-12:54 pm
1 stop5h 54m
Chicago O'Hare Intl
Sat 8/29
6:59 am-10:29 am
1 stop3h 30m
$259
AppletonChicago
ATW - ORD
ATWORD
Appleton Intl
Fri 7/10
7:15 pm-8:55 pm
Nonstop1h 40m
Chicago O'Hare Intl
Tue 7/14
5:03 pm-6:18 pm
Nonstop1h 15m
$269
AppletonChicago
ATW - ORD
ATWORD
Appleton Intl
Sat 7/11
2:40 pm-4:00 pm
Nonstop1h 20m
Chicago O'Hare Intl
Wed 7/15
10:25 am-11:43 am
Nonstop1h 18m
$269
AppletonChicago
ATW - MDW
ATWMDW
Appleton Intl
Fri 7/10
11:27 am-6:18 pm
1 stop6h 51m
Chicago Midway
Tue 7/14
1:18 pm-5:50 pm
1 stop4h 32m
$289
Showing 1-10 of 41 resultsSorted by cheapest first
Best time to book a flight from Oshkosh to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Oshkosh with our price prediction graph.
ATW-ORD
ATW-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 Oshkosh to Chicago
OS9-CHI
ATW-ORD
ATW-MDW
What is the cheapest time of day to fly from OS9 to CHI?
Find hourly flight availability from Oshkosh 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 30, 2026.
Unlike in the evening, when flights are generally more expensive, you can save up to 23% on flights from Oshkosh to Chicago by exploring options for tickets in the morning.
Weekly flight availability from Oshkosh to Chicago
Explore weekly flight availability from Oshkosh 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 30, 2026.
The most flights from OS9 to CHI are scheduled on a Tuesday (56 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (9 on average).
What is the cheapest day to fly from Oshkosh to Chicago?
Use this chart to determine the cheapest time to fly round-trip from Oshkosh to Chicago. Price data was last updated on June 27, 2026.
Travelers seeking maximum savings on their Oshkosh to Chicago flight should consider departing on Friday evenings 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.
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated June 30, 2026.
Read through reviews of airlines operating flights from Oshkosh to Chicago, such as United Airlines and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Comfort
7.3
Boarding
7.7
Food
6.6
Entertainment
7.1
Crew
8.1
Overall
7.4
Reviews
1 / 20
2.0
MediocreDeb,Jan 2025
MKE - ORD
Comfort
7.3
Boarding
7.7
Food
6.6
Entertainment
7.1
Crew
8.1
Overall
7.4
Reviews
1 / 20
2.0
MediocreDeb,Jan 2025
MKE - ORD
Comfort
7.3
Boarding
7.7
Food
6.6
Entertainment
7.1
Crew
8.1
Overall
7.4
Reviews
1 / 20
2.0
MediocreDeb,Jan 2025
MKE - ORD
Related info for your journey
Find useful and relevant information for your journey from Oshkosh 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
Hammond
Lansing
Merrillville
Valparaiso
Porter
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Alternative routes for Oshkosh to Chicago
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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 30, 2026.
Complete your trip
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Oshkosh and Chicago flights
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Oshkosh to Chicago flights
Consider these flights traveling from Oshkosh to Chicago.
Top 2 airlines flying from Oshkosh to Chicago
Discover the top 2 airlines that operate flights from Oshkosh 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 30, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$179 | Average$283 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$179 | Average$274 | FlexibilityNo cancel fee | On-time69% |