$103+ 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 5/24. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — CHI
May 30 — Jun 61
Round-trip
1 adult, Economy
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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 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 April 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 April 30, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/28. 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 5/242:44 pm
ATW
- ORD
2 stops41h 11m
Multiple Airlines
Thu 5/289:37 pm
ORD
- ATW
1 stop25h 12m
Multiple Airlines
Deal found 4/28![Multiple Airlines logo]()
$226
This American Airlines deal was found by Cheapflights users on 4/28. 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.
Tue 6/1611:16 am
ATW
- ORD
Nonstop1h 20m
American Airlines
Tue 6/239:30 am
ORD
- ATW
Nonstop1h 16m
American Airlines
Deal found 4/28![American Airlines logo]()
$239
This American Airlines deal was found by Cheapflights users on 4/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/275:35 am
ATW
- ORD
Nonstop1h 23m
American Airlines
Wed 6/35:10 am
ORD
- ATW
1 stop8h 24m
American Airlines
Deal found 4/29![American Airlines logo]()
$248
This American Airlines deal was found by Cheapflights users on 4/28. 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 5/156:30 pm
ATW
- ORD
Nonstop1h 32m
American Airlines
Sat 5/3011:40 am
ORD
- ATW
Nonstop1h 15m
American Airlines
Deal found 4/28![American Airlines logo]()
$254
This Delta deal was found by Cheapflights users on 4/27. 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.
Wed 5/2012:32 pm
ATW
- MDW
1 stop5h 24m
Delta
Wed 5/277:13 pm
MDW
- ATW
1 stop3h 41m
Delta
Deal found 4/27![Delta logo]()
$259
This Delta deal was found by Cheapflights users on 4/28. 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 6/162:07 pm
ATW
- ORD
1 stop6h 24m
Delta
Tue 6/237:01 am
ORD
- ATW
1 stop3h 28m
Delta
Deal found 4/28![Delta logo]()
$259
This Delta deal was found by Cheapflights users on 4/26. 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 6/1711:27 am
ATW
- ORD
2 stops9h 04m
Delta
Sat 6/206:30 am
ORD
- ATW
1 stop4h 17m
Delta
Deal found 4/26![Delta logo]()
$264
This Delta deal was found by Cheapflights users on 4/26. 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.
Mon 6/296:00 am
ATW
- ORD
2 stops7h 04m
Delta
Wed 7/156:30 am
ORD
- ATW
2 stops6h 53m
Delta
Deal found 4/26![Delta logo]()
$269
This Kiwi.com deal was found by Cheapflights users on 4/26. 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.
Mon 6/299:36 am
ATW
- ORD
1 stop29h 51m
Multiple Airlines
Thu 7/167:07 pm
ORD
- ATW
1 stop13h 39m
Multiple Airlines
Deal found 4/26![Multiple Airlines logo]()
$277
This Delta deal was found by Cheapflights users on 4/26. 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 7/172:03 pm
ATW
- MDW
1 stop4h 22m
Delta
Sat 7/181:18 pm
MDW
- ATW
1 stop3h 20m
Delta
Deal found 4/26![Delta logo]()
$283
This American Airlines deal was found by Cheapflights users on 4/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/177:15 pm
ATW
- ORD
Nonstop1h 40m
American Airlines
Sun 7/1911:00 pm
ORD
- ATW
Nonstop1h 10m
American Airlines
Deal found 4/29![American Airlines logo]()
$283
This United Airlines deal was found by Cheapflights users on 4/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/812:33 pm
ATW
- ORD
Nonstop1h 26m
United Airlines
Mon 5/117:20 am
ORD
- ATW
Nonstop1h 14m
United Airlines
Deal found 4/27![United Airlines logo]()
$284
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 April 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 April 30, 2026.
This Delta deal was found by Cheapflights users on 4/26. 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 5/2012:32 pm
ATW
- MDW
1 stop5h 24m
Delta
Wed 5/277:13 pm
MDW
- ATW
1 stop3h 41m
Delta
Deal found 4/26![Delta logo]()
$259
This United Airlines deal was found by Cheapflights users on 4/25. 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.
Fri 6/266:20 am
ATW
- ORD
Nonstop1h 31m
United Airlines
Tue 6/309:37 pm
ORD
- ATW
Nonstop1h 23m
United Airlines
Deal found 4/25![United Airlines logo]()
$324
This American Airlines deal was found by Cheapflights users on 4/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/165:00 am
ATW
- ORD
Nonstop1h 22m
American Airlines
Thu 6/189:30 am
ORD
- ATW
Nonstop1h 16m
American Airlines
Deal found 4/29![American Airlines logo]()
$327
This Kiwi.com deal was found by Cheapflights users on 4/29. 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.
Sat 5/1610:15 am
ATW
- MDW
1 stop22h 11m
Multiple Airlines
Wed 5/206:00 am
MDW
- ATW
2 stops39h 52m
Multiple Airlines
Deal found 4/29![Multiple Airlines logo]()
$374
This Delta deal was found by Cheapflights users on 4/29. 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 5/2712:32 pm
ATW
- MDW
1 stop5h 24m
Delta
Wed 6/37:13 pm
MDW
- ATW
1 stop3h 41m
Delta
Deal found 4/29![Delta logo]()
$259
This Delta deal was found by Cheapflights users on 4/25. 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.
Tue 6/162:07 pm
ATW
- ORD
1 stop6h 24m
Delta
Tue 6/237:01 am
ORD
- ATW
1 stop3h 28m
Delta
Deal found 4/25![Delta logo]()
$259
This Delta deal was found by Cheapflights users on 4/29. 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 5/2712:32 pm
ATW
- ORD
1 stop4h 19m
Delta
Wed 6/36:24 am
ORD
- ATW
1 stop5h 27m
Delta
Deal found 4/29![Delta logo]()
$259
This Delta deal was found by Cheapflights users on 4/26. 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 5/2012:32 pm
ATW
- ORD
1 stop6h 48m
Delta
Sat 5/231:44 pm
ORD
- ATW
1 stop3h 50m
Delta
Deal found 4/26![Delta logo]()
$259
This Delta deal was found by Cheapflights users on 4/28. 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.
Wed 5/207:00 am
ATW
- ORD
1 stop6h 01m
Delta
Wed 5/275:41 pm
ORD
- ATW
1 stop5h 13m
Delta
Deal found 4/28![Delta logo]()
$259
This Delta deal was found by Cheapflights users on 4/25. 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.
Thu 7/211:27 am
ATW
- ORD
1 stop3h 38m
Delta
Sun 7/57:01 am
ORD
- ATW
1 stop6h 26m
Delta
Deal found 4/25![Delta logo]()
$259
This Delta deal was found by Cheapflights users on 4/26. 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.
Tue 5/1912:32 pm
ATW
- ORD
1 stop6h 48m
Delta
Sat 5/235:19 pm
ORD
- ATW
1 stop3h 55m
Delta
Deal found 4/26![Delta logo]()
$259
This Kiwi.com deal was found by Cheapflights users on 4/25. 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.
Fri 8/79:36 am
ATW
- MDW
2 stops12h 32m
Multiple Airlines
Sun 8/99:14 am
MDW
- ATW
1 stop8h 22m
Multiple Airlines
Deal found 4/25![Multiple Airlines logo]()
$492
This Delta deal was found by Cheapflights users on 4/26. 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 7/172:03 pm
ATW
- MDW
1 stop4h 22m
Delta
Sat 7/181:18 pm
MDW
- ATW
1 stop3h 20m
Delta
Deal found 4/26![Delta logo]()
$283
This Delta deal was found by Cheapflights users on 4/29. 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 6/54:13 pm
ATW
- ORD
1 stop5h 07m
Delta
Thu 6/116:30 am
ORD
- ATW
1 stop4h 17m
Delta
Deal found 4/29![Delta logo]()
$289
This Delta deal was found by Cheapflights users on 4/26. 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 7/172:03 pm
ATW
- ORD
1 stop6h 28m
Delta
Sat 7/186:25 pm
ORD
- ATW
1 stop4h 31m
Delta
Deal found 4/26![Delta logo]()
$319
This Delta deal was found by Cheapflights users on 4/28. 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.
Fri 5/154:13 pm
ATW
- ORD
1 stop5h 07m
Delta
Sat 5/306:24 am
ORD
- ATW
1 stop5h 27m
Delta
Deal found 4/28![Delta logo]()
$338
This Delta deal was found by Cheapflights users on 4/29. 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.
Sat 5/1612:32 pm
ATW
- MDW
1 stop5h 24m
Delta
Wed 5/201:22 pm
MDW
- ATW
1 stop4h 12m
Delta
Deal found 4/29![Delta logo]()
$344
This Delta deal was found by Cheapflights users on 4/27. 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 6/17:00 am
ATW
- MDW
1 stop5h 42m
Delta
Fri 6/57:13 pm
MDW
- ATW
1 stop3h 41m
Delta
Deal found 4/27![Delta logo]()
$347
This Delta deal was found by Cheapflights users on 4/28. 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 6/92:07 pm
ATW
- MDW
1 stop4h 24m
Delta
Wed 6/109:17 am
MDW
- ATW
1 stop4h 10m
Delta
Deal found 4/28![Delta logo]()
$373
This Delta deal was found by Cheapflights users on 4/25. 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 8/72:03 pm
ATW
- MDW
1 stop4h 22m
Delta
Sun 8/99:20 am
MDW
- ATW
1 stop4h 03m
Delta
Deal found 4/25![Delta logo]()
$439
This Delta deal was found by Cheapflights users on 4/28. 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.
Sun 5/1712:32 pm
ATW
- MDW
1 stop5h 24m
Delta
Thu 5/211:22 pm
MDW
- ATW
1 stop4h 12m
Delta
Deal found 4/28![Delta logo]()
$469
This Delta deal was found by Cheapflights users on 4/27. 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.
Sun 8/27:00 am
ATW
- MDW
1 stop5h 38m
Delta
Fri 8/79:20 am
MDW
- ATW
1 stop4h 03m
Delta
Deal found 4/27![Delta logo]()
$479
Last-minute flights from Oshkosh to ChicagoDiscover last-minute flight deals from Oshkosh to Chicago. Data last updated April 30, 2026 and is based on user searches.
Discover last-minute flight deals from Oshkosh to Chicago. Data last updated April 30, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 4/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/76:30 pm
ATW
- ORD
Nonstop1h 32m
American Airlines
Sun 5/108:55 am
ORD
- ATW
Nonstop1h 10m
American Airlines
Deal found 4/29![American Airlines logo]()
$299
This United Airlines deal was found by Cheapflights users on 4/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/812:33 pm
ATW
- ORD
Nonstop1h 26m
United Airlines
Mon 5/117:20 am
ORD
- ATW
Nonstop1h 14m
United Airlines
Deal found 4/27![United Airlines logo]()
$284
This Delta deal was found by Cheapflights users on 4/27. 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 5/127:00 am
ATW
- ORD
1 stop6h 01m
Delta
Sat 5/166:24 am
ORD
- ATW
1 stop5h 27m
Delta
Deal found 4/27![Delta logo]()
$289
This American Airlines deal was found by Cheapflights users on 4/28. 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 5/156:30 pm
ATW
- ORD
Nonstop1h 32m
American Airlines
Sat 5/3011:40 am
ORD
- ATW
Nonstop1h 15m
American Airlines
Deal found 4/28![American Airlines logo]()
$254
This Delta deal was found by Cheapflights users on 4/29. 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.
Sat 5/167:00 am
ATW
- ORD
1 stop5h 56m
Delta
Wed 5/207:00 am
ORD
- ATW
1 stop3h 28m
Delta
Deal found 4/29![Delta logo]()
$274
This Kiwi.com deal was found by Cheapflights users on 4/28. 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 5/176:30 am
ATW
- ORD
2 stops25h 25m
Multiple Airlines
Thu 5/219:37 pm
ORD
- ATW
1 stop25h 42m
Multiple Airlines
Deal found 4/28![Multiple Airlines logo]()
$285
This American Airlines deal was found by Cheapflights users on 4/28. 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.
Wed 5/205:40 am
ATW
- ORD
Nonstop1h 27m
American Airlines
Wed 5/274:51 pm
ORD
- ATW
Nonstop1h 18m
American Airlines
Deal found 4/28![American Airlines logo]()
$239
This Delta deal was found by Cheapflights users on 4/27. 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.
Wed 5/2012:32 pm
ATW
- MDW
1 stop5h 24m
Delta
Wed 5/277:13 pm
MDW
- ATW
1 stop3h 41m
Delta
Deal found 4/27![Delta logo]()
$259
This Delta deal was found by Cheapflights users on 4/28. 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.
Wed 5/207:00 am
ATW
- ORD
1 stop6h 01m
Delta
Wed 5/275:41 pm
ORD
- ATW
1 stop5h 13m
Delta
Deal found 4/28![Delta logo]()
$259
This Kiwi.com deal was found by Cheapflights users on 4/28. 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 5/242:44 pm
ATW
- ORD
2 stops41h 11m
Multiple Airlines
Thu 5/289:37 pm
ORD
- ATW
1 stop25h 12m
Multiple Airlines
Deal found 4/28![Multiple Airlines logo]()
$226
This American Airlines deal was found by Cheapflights users on 4/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/275:35 am
ATW
- ORD
Nonstop1h 23m
American Airlines
Wed 6/35:10 am
ORD
- ATW
1 stop8h 24m
American Airlines
Deal found 4/29![American Airlines logo]()
$248
This Delta deal was found by Cheapflights users on 4/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/287:00 am
ATW
- ORD
1 stop6h 01m
Delta
Thu 6/46:24 am
ORD
- ATW
1 stop5h 27m
Delta
Deal found 4/30![Delta logo]()
$283
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 April 30, 2026.
Search for one-way flight options from Oshkosh to Chicago. Find affordable one-way fares based on user searches. Data last updated April 30, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/29. 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 5/242:44 pm
ATW
- ORD
1 stop8h 29m
Multiple Airlines
Deal found 4/29![Multiple Airlines logo]()
$103
This Kiwi.com deal was found by Cheapflights users on 4/28. 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 6/229:41 am
ATW
- ORD
1 stop26h 43m
Multiple Airlines
Deal found 4/28![Multiple Airlines logo]()
$129
This Kiwi.com deal was found by Cheapflights users on 4/29. 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 6/89:36 am
ATW
- ORD
2 stops46h 27m
Multiple Airlines
Deal found 4/29![Multiple Airlines logo]()
$133
This Kiwi.com deal was found by Cheapflights users on 4/29. 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 6/299:36 am
ATW
- ORD
1 stop29h 51m
Multiple Airlines
Deal found 4/29![Multiple Airlines logo]()
$134
This Kiwi.com deal was found by Cheapflights users on 4/26. 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.
Mon 5/259:36 am
ATW
- ORD
2 stops46h 19m
Multiple Airlines
Deal found 4/26![Multiple Airlines logo]()
$135
This Kiwi.com deal was found by Cheapflights users on 4/25. 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.
Fri 6/269:36 am
ATW
- ORD
1 stop14h 23m
Multiple Airlines
Deal found 4/25![Multiple Airlines logo]()
$145
This Kiwi.com deal was found by Cheapflights users on 4/29. 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 6/159:41 am
ATW
- MDW
2 stops36h 30m
Multiple Airlines
Deal found 4/29![Multiple Airlines logo]()
$171
This Delta deal was found by Cheapflights users on 4/29. 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 6/122:07 pm
ATW
- MDW
1 stop4h 24m
Delta
Deal found 4/29![Delta logo]()
$174
This Delta deal was found by Cheapflights users on 4/29. 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 6/177:00 am
ATW
- MDW
2 stops11h 18m
Delta
Deal found 4/29![Delta logo]()
$179
This Kiwi.com deal was found by Cheapflights users on 4/28. 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.
Sat 6/275:34 pm
ATW
- MDW
3 stops41h 35m
Multiple Airlines
Deal found 4/28![Multiple Airlines logo]()
$197
This Delta deal was found by Cheapflights users on 4/29. 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.
Thu 6/182:07 pm
ATW
- MDW
1 stop4h 24m
Delta
Deal found 4/29![Delta logo]()
$200
This Kiwi.com deal was found by Cheapflights users on 4/29. 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.
Thu 6/182:44 pm
ATW
- MDW
2 stops31h 27m
Multiple Airlines
Deal found 4/29![Multiple Airlines logo]()
$204
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 April 30, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $226 (Kiwi.com) |
One-way from | $103 (Kiwi.com) |
Popular in | November |
Cheapest in | February |
Average price | $269 |
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 April 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
AppletonChicago
ATW - MDW
ATWMDW
Appleton Intl
Wed 5/20
12:32 pm-5:56 pm
1 stop5h 24m
Chicago Midway
Wed 5/27
7:13 pm-10:54 pm
1 stop3h 41m
$259
AppletonChicago
ATW - MDW
ATWMDW
Appleton Intl
Wed 5/27
12:32 pm-5:56 pm
1 stop5h 24m
Chicago Midway
Wed 6/3
7:13 pm-10:54 pm
1 stop3h 41m
$259
AppletonChicago
ATW - ORD
ATWORD
Appleton Intl
Tue 6/16
2:07 pm-8:31 pm
1 stop6h 24m
Chicago O'Hare Intl
Tue 6/23
7:01 am-10:29 am
1 stop3h 28m
$259
AppletonChicago
ATW - ORD
ATWORD
Appleton Intl
Wed 5/27
12:32 pm-4:51 pm
1 stop4h 19m
Chicago O'Hare Intl
Wed 6/3
6:24 am-11:51 am
1 stop5h 27m
$259
AppletonChicago
ATW - ORD
ATWORD
Appleton Intl
Wed 5/20
12:32 pm-7:20 pm
1 stop6h 48m
Chicago O'Hare Intl
Sat 5/23
1:44 pm-5:34 pm
1 stop3h 50m
$259
AppletonChicago
ATW - ORD
ATWORD
Appleton Intl
Wed 5/20
7:00 am-1:01 pm
1 stop6h 01m
Chicago O'Hare Intl
Wed 5/27
5:41 pm-10:54 pm
1 stop5h 13m
$259
AppletonChicago
ATW - ORD
ATWORD
Appleton Intl
Thu 7/2
11:27 am-3:05 pm
1 stop3h 38m
Chicago O'Hare Intl
Sun 7/5
7:01 am-1:27 pm
1 stop6h 26m
$259
AppletonChicago
ATW - ORD
ATWORD
Appleton Intl
Tue 5/19
12:32 pm-7:20 pm
1 stop6h 48m
Chicago O'Hare Intl
Sat 5/23
5:19 pm-9:14 pm
1 stop3h 55m
$259
AppletonChicago
ATW - MDW
ATWMDW
Appleton Intl
Fri 7/17
2:03 pm-6:25 pm
1 stop4h 22m
Chicago Midway
Sat 7/18
1:18 pm-4:38 pm
1 stop3h 20m
$283
AppletonChicago
ATW - ORD
ATWORD
Appleton Intl
Fri 6/5
4:13 pm-9:20 pm
1 stop5h 07m
Chicago O'Hare Intl
Thu 6/11
6:30 am-10:47 am
1 stop4h 17m
$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 April 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.
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 April 25, 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.
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 April 30, 2026.
The most flights from OS9 to CHI are scheduled on a Thursday (70 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (42 on average).
How much does it cost to fly round-trip from Oshkosh to Chicago?
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 April 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.
Food
6.6
Comfort
7.3
Boarding
7.7
Overall
7.4
Crew
8.1
Entertainment
7.1
Reviews
1 / 20
8.0
ExcellentAnonymous,Apr 2026
DFW - EWR
Food
6.6
Comfort
7.3
Boarding
7.7
Overall
7.4
Crew
8.1
Entertainment
7.1
Reviews
1 / 20
8.0
ExcellentAnonymous,Apr 2026
DFW - EWR
Food
6.6
Comfort
7.3
Boarding
7.7
Overall
7.4
Crew
8.1
Entertainment
7.1
Reviews
1 / 20
8.0
ExcellentAnonymous,Apr 2026
DFW - EWR
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
Lansing
Merrillville
Hammond
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 April 30, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
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Oshkosh and Chicago flights
Browse other Oshkosh and Chicago flight options. Last updated on April 30, 2026.
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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 April 30, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$179 | Average$255 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$179 | Average$270 | FlexibilityNo cancel fee | On-time69% |