$126+ 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 9/21. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — CHI
Sep 24 — Oct 11
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Oshkosh 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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Oshkosh to Chicago
Cheapest
Best
Last-minute
One-way
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 August 25, 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 August 25, 2026.
This American Airlines deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” 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 9/256:31 pm -
Nonstop1h 42m
Sat 10/109:48 am -
Nonstop1h 15m
Deal found 8/21![American Airlines logo]()
$249
This Kiwi.com deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” 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 9/215:56 pm -
1 stop21h 24m
Fri 9/257:11 am -
1 stop9h 09m
Deal found 8/21![Multiple Airlines logo]()
$250
This United Airlines deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 9/1912:18 pm -
Nonstop1h 26m
Sun 9/205:50 pm -
Nonstop1h 15m
Deal found 8/24![United Airlines logo]()
$256
This United Airlines deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” 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 9/1010:00 am -
Nonstop1h 29m
Wed 9/1612:45 pm -
Nonstop1h 17m
Deal found 8/22![United Airlines logo]()
$264
This Delta deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” 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 10/105:34 pm -
1 stop3h 53m
Fri 10/236:20 am -
1 stop5h 18m
Deal found 8/21![Delta logo]()
$269
This United Airlines deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/49:10 am -
Nonstop1h 30m
Tue 9/82:15 pm -
Nonstop1h 18m
Deal found 8/20![United Airlines logo]()
$279
This Delta deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” 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 9/54:10 pm -
1 stop5h 37m
Sat 9/266:10 am -
1 stop4h 07m
Deal found 8/21![Delta logo]()
$284
This United Airlines deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” 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 12/209:45 am -
Nonstop1h 47m
Sun 12/275:45 pm -
Nonstop1h 29m
Deal found 8/23![United Airlines logo]()
$285
This Delta deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 9/195:07 pm -
1 stop3h 23m
Sun 9/206:10 am -
1 stop4h 07m
Deal found 8/24![Delta logo]()
$289
This Delta deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” 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 9/102:00 pm -
1 stop6h 30m
Wed 9/166:10 am -
1 stop4h 07m
Deal found 8/22![Delta logo]()
$293
This American Airlines deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” 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 9/15:42 am -
Nonstop1h 18m
Sat 9/511:00 pm -
Nonstop1h 10m
Deal found 8/20![American Airlines logo]()
$294
This Delta deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” 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 9/42:06 pm -
1 stop4h 27m
Tue 9/89:29 am -
1 stop3h 49m
Deal found 8/20![Delta logo]()
$299
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 August 25, 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 August 25, 2026.
This United Airlines deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” 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 10/106:25 am -
Nonstop1h 27m
Fri 10/235:50 pm -
Nonstop1h 17m
Deal found 8/22![United Airlines logo]()
$249
This Delta deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” 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 1/105:25 pm -
1 stop4h 12m
Sun 1/176:00 am -
1 stop5h 27m
Deal found 8/20![Delta logo]()
$269
This United Airlines deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” 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 10/96:25 am -
Nonstop1h 27m
Sat 10/105:50 pm -
Nonstop1h 17m
Deal found 8/23![United Airlines logo]()
$249
This Delta deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” 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 10/105:34 pm -
1 stop3h 53m
Fri 10/236:20 am -
1 stop5h 18m
Deal found 8/22![Delta logo]()
$269
This United Airlines deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” 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 9/145:00 pm -
Nonstop1h 31m
Sun 9/202:15 pm -
Nonstop1h 18m
Deal found 8/21![United Airlines logo]()
$249
This Delta deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 9/195:07 pm -
1 stop3h 23m
Sun 9/206:10 am -
1 stop4h 07m
Deal found 8/24![Delta logo]()
$269
This United Airlines deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/49:10 am -
Nonstop1h 30m
Tue 9/82:15 pm -
Nonstop1h 18m
Deal found 8/20![United Airlines logo]()
$279
This Delta deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” 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 10/22:00 pm -
1 stop6h 30m
Sun 10/46:10 am -
1 stop4h 07m
Deal found 8/21![Delta logo]()
$284
This United Airlines deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” 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 9/56:00 am -
Nonstop1h 29m
Wed 9/95:45 pm -
Nonstop1h 15m
Deal found 8/21![United Airlines logo]()
$279
This Delta deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” 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 9/42:06 pm -
1 stop4h 27m
Tue 9/89:29 am -
1 stop3h 49m
Deal found 8/20![Delta logo]()
$299
This United Airlines deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” 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 12/209:45 am -
Nonstop1h 47m
Sun 12/275:45 pm -
Nonstop1h 29m
Deal found 8/23![United Airlines logo]()
$285
This Delta deal was found by Cheapflights users on 8/25. 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.
Wed 9/911:09 am -
1 stop5h 48m
Sun 9/137:13 pm -
1 stop3h 49m
Deal found 8/25![Delta logo]()
$319
This Delta deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” 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 10/237:00 am -
1 stop5h 47m
Fri 10/3010:01 am -
1 stop6h 40m
Deal found 8/22![Delta logo]()
$323
This Delta deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” 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 10/297:00 am -
1 stop5h 47m
Mon 11/25:31 pm -
1 stop4h 03m
Deal found 8/21![Delta logo]()
$369
This Delta deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” 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 9/1011:09 am -
1 stop5h 48m
Wed 9/169:29 am -
1 stop3h 49m
Deal found 8/22![Delta logo]()
$437
This Delta deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” 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 9/252:00 pm -
1 stop4h 33m
Sat 10/105:31 pm -
1 stop4h 03m
Deal found 8/21![Delta logo]()
$484
This Delta deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” 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 9/252:00 pm -
1 stop4h 33m
Sun 9/279:29 am -
1 stop3h 49m
Deal found 8/22![Delta logo]()
$499
This Delta deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” 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 9/307:00 am -
1 stop5h 39m
Thu 10/19:29 am -
1 stop3h 49m
Deal found 8/21![Delta logo]()
$584
This Delta deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/77:00 am -
1 stop5h 39m
Fri 9/117:13 pm -
1 stop3h 49m
Deal found 8/23![Delta logo]()
$667
Last-minute flights from Oshkosh to ChicagoDiscover last-minute flight deals from Oshkosh to Chicago. Data last updated August 25, 2026 and is based on user searches.
Discover last-minute flight deals from Oshkosh to Chicago. Data last updated August 25, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” 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 9/15:42 am -
Nonstop1h 18m
Sat 9/511:00 pm -
Nonstop1h 10m
Deal found 8/20![American Airlines logo]()
$294
This Delta deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” 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 9/111:09 am -
1 stop5h 50m
Sat 9/55:45 pm -
1 stop3h 52m
Deal found 8/20![Delta logo]()
$314
This United Airlines deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/49:10 am -
Nonstop1h 30m
Tue 9/82:15 pm -
Nonstop1h 18m
Deal found 8/20![United Airlines logo]()
$279
This Delta deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” 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 9/42:06 pm -
1 stop4h 27m
Tue 9/89:29 am -
1 stop3h 49m
Deal found 8/20![Delta logo]()
$299
This Delta deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” 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 9/42:06 pm -
1 stop6h 24m
Tue 9/88:55 am -
1 stop4h 23m
Deal found 8/20![Delta logo]()
$299
This Delta deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” 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 9/54:10 pm -
1 stop5h 37m
Sat 9/266:10 am -
1 stop4h 07m
Deal found 8/21![Delta logo]()
$284
This United Airlines deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” 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 9/1010:00 am -
Nonstop1h 29m
Wed 9/1612:45 pm -
Nonstop1h 17m
Deal found 8/22![United Airlines logo]()
$264
This Delta deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” 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 9/102:00 pm -
1 stop6h 30m
Wed 9/166:10 am -
1 stop4h 07m
Deal found 8/22![Delta logo]()
$293
This United Airlines deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 9/1912:18 pm -
Nonstop1h 26m
Sun 9/205:50 pm -
Nonstop1h 15m
Deal found 8/24![United Airlines logo]()
$256
This Delta deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 9/195:07 pm -
1 stop3h 23m
Sun 9/206:10 am -
1 stop4h 07m
Deal found 8/24![Delta logo]()
$269
This Kiwi.com deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” 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 9/215:56 pm -
1 stop21h 24m
Fri 9/257:11 am -
1 stop9h 09m
Deal found 8/21![Multiple Airlines logo]()
$250
This American Airlines deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” 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 9/256:31 pm -
Nonstop1h 42m
Sat 10/109:48 am -
Nonstop1h 15m
Deal found 8/21![American Airlines logo]()
$249
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 August 25, 2026.
Search for one-way flight options from Oshkosh to Chicago. Find affordable one-way fares based on user searches. Data last updated August 25, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” 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 9/215:56 pm -
1 stop21h 24m
Deal found 8/21![Multiple Airlines logo]()
$126
This Kiwi.com deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/255:10 pm -
1 stop22h 10m
Deal found 8/21![Multiple Airlines logo]()
$128
This Kiwi.com deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” 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 10/27:11 pm -
1 stop20h 09m
Deal found 8/20![Multiple Airlines logo]()
$133
This Kiwi.com deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” 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 10/197:11 pm -
1 stop20h 25m
Deal found 8/23![Multiple Airlines logo]()
$139
This Kiwi.com deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” 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 9/204:10 pm -
1 stop18h 10m
Deal found 8/22![Multiple Airlines logo]()
$162
This Kiwi.com deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” 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 10/237:12 pm -
1 stop20h 24m
Deal found 8/21![Multiple Airlines logo]()
$164
This Kiwi.com deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/185:10 pm -
2 stops42h 30m
Deal found 8/21![Multiple Airlines logo]()
$166
This Kiwi.com deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” 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 10/27:11 pm -
2 stops22h 40m
Deal found 8/20![Multiple Airlines logo]()
$172
This Kiwi.com deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 10/197:11 pm -
3 stops28h 32m
Deal found 8/24![Multiple Airlines logo]()
$232
This Delta deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” 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 10/22:00 pm -
1 stop4h 33m
Deal found 8/20![Delta logo]()
$249
This Delta deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” 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 2/156:30 am -
1 stop5h 21m
Deal found 8/22![Delta logo]()
$310
This Delta deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” 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 9/611:00 am -
1 stop4h 57m
Deal found 8/21![Delta logo]()
$324
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 August 25, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $249 (American Airlines) |
One-way from | $126 (Kiwi.com) |
Popular in | August |
Cheapest in | February |
Average price | $675 |
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 7,457,451 searches. Data last updated August 25, 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 Appleton Intl - ORD Chicago O'Hare Intl
ATWORD
Appleton Intl
Sat 10/10
6:25 am-7:52 am
Nonstop1h 27m
Chicago O'Hare Intl
Fri 10/23
5:50 pm-7:07 pm
Nonstop1h 17m
$249
AppletonChicago
ATW Appleton Intl - ORD Chicago O'Hare Intl
ATWORD
Appleton Intl
Fri 10/9
6:25 am-7:52 am
Nonstop1h 27m
Chicago O'Hare Intl
Sat 10/10
5:50 pm-7:07 pm
Nonstop1h 17m
$249
AppletonChicago
ATW Appleton Intl - ORD Chicago O'Hare Intl
ATWORD
Appleton Intl
Mon 9/14
5:00 pm-6:31 pm
Nonstop1h 31m
Chicago O'Hare Intl
Sun 9/20
2:15 pm-3:33 pm
Nonstop1h 18m
$249
AppletonChicago
ATW Appleton Intl - ORD Chicago O'Hare Intl
ATWORD
Appleton Intl
Sun 1/10
5:25 pm-9:37 pm
1 stop4h 12m
Chicago O'Hare Intl
Sun 1/17
6:00 am-11:27 am
1 stop5h 27m
$269
AppletonChicago
ATW Appleton Intl - ORD Chicago O'Hare Intl
ATWORD
Appleton Intl
Sat 10/10
5:34 pm-9:27 pm
1 stop3h 53m
Chicago O'Hare Intl
Fri 10/23
6:20 am-11:38 am
1 stop5h 18m
$269
AppletonChicago
ATW Appleton Intl - ORD Chicago O'Hare Intl
ATWORD
Appleton Intl
Sat 9/19
5:07 pm-8:30 pm
1 stop3h 23m
Chicago O'Hare Intl
Sun 9/20
6:10 am-10:17 am
1 stop4h 07m
$269
AppletonChicago
ATW Appleton Intl - ORD Chicago O'Hare Intl
ATWORD
Appleton Intl
Fri 9/4
9:10 am-10:40 am
Nonstop1h 30m
Chicago O'Hare Intl
Tue 9/8
2:15 pm-3:33 pm
Nonstop1h 18m
$279
AppletonChicago
ATW Appleton Intl - ORD Chicago O'Hare Intl
ATWORD
Appleton Intl
Sat 9/5
6:00 am-7:29 am
Nonstop1h 29m
Chicago O'Hare Intl
Wed 9/9
5:45 pm-7:00 pm
Nonstop1h 15m
$279
AppletonChicago
ATW Appleton Intl - ORD Chicago O'Hare Intl
ATWORD
Appleton Intl
Fri 10/2
2:00 pm-8:30 pm
1 stop6h 30m
Chicago O'Hare Intl
Sun 10/4
6:10 am-10:17 am
1 stop4h 07m
$284
AppletonChicago
ATW Appleton Intl - ORD Chicago O'Hare Intl
ATWORD
Appleton Intl
Sun 12/20
9:45 am-11:32 am
Nonstop1h 47m
Chicago O'Hare Intl
Sun 12/27
5:45 pm-7:14 pm
Nonstop1h 29m
$285
Showing 1-10 of 39 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 August 25, 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 August 25, 2026.
The most flights from OS9 to CHI are scheduled on a Friday (62 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (40 on average).
How much does it cost to fly round-trip from Oshkosh to Chicago?
Airfare is below average for this route at the moment.
Oshkosh to Chicago flights typically cost between $321 and $537 in September.The cheapest round-trip price found within the last 5 days was $249 on American Airlines (Sep 25-Oct 10).
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 August 22, 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. Monday at noon 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 August 25, 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.
Boarding
7.7
Crew
8.1
Entertainment
7.1
Overall
7.4
Comfort
7.3
Food
6.7
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Boarding
7.7
Crew
8.1
Entertainment
7.1
Overall
7.4
Comfort
7.3
Food
6.7
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Boarding
7.7
Crew
8.1
Entertainment
7.1
Overall
7.4
Comfort
7.3
Food
6.7
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - 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
Lansing
Merrillville
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
Flights by cabin class
Other flight options
Popular flights
Top destinations
Alternative routes for Oshkosh 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 August 25, 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 Oshkosh to Chicago by cabin class
Find flights from Oshkosh to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Oshkosh and Chicago flights
Browse other Oshkosh and Chicago flight options. Last updated on August 25, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
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 7,457,451 searches. Data last updated August 25, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$149 | Average$277 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$179 | Average$286 | FlexibilityNo cancel fee | On-time71% |