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$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 5/3. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — CHI
Apr 9 — Apr 161
Thu 4/9
Thu 4/16
1 adult, Economy
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Cheap flight deals from Oshkosh to Chicago

Cheapest flights from Oshkosh to Chicago
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 March 10, 2026.

This American Airlines deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/81:30 pm
ATW
-
ORD
Nonstop1h 27m
American Airlines
Fri 4/174:47 pm
ORD
-
ATW
Nonstop1h 14m
American Airlines
Deal found 3/6$199
This American Airlines deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/256:39 pm
ATW
-
ORD
Nonstop1h 20m
American Airlines
Sun 4/124:47 pm
ORD
-
ATW
Nonstop1h 14m
American Airlines
Deal found 3/8$214
This Delta deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/37:00 am
ATW
-
MDW
1 stop5h 29m
Delta
Fri 4/101:10 pm
MDW
-
ATW
1 stop4h 32m
Delta
Deal found 3/6$219
This Delta deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/77:00 am
ATW
-
ORD
1 stop6h 01m
Delta
Sun 5/106:24 am
ORD
-
ATW
1 stop5h 27m
Delta
Deal found 3/9$219
This American Airlines deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/209:38 am
ATW
-
ORD
Nonstop1h 15m
American Airlines
Tue 3/2410:15 pm
ORD
-
ATW
Nonstop1h 04m
American Airlines
Deal found 3/6$229
This Delta deal was found by Cheapflights users on 3/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/317:00 am
ATW
-
MDW
1 stop5h 29m
Delta
Sat 4/41:10 pm
MDW
-
ATW
1 stop4h 20m
Delta
Deal found 3/7$234
This American Airlines deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/245:40 am
ATW
-
ORD
Nonstop1h 16m
American Airlines
Tue 3/3110:15 pm
ORD
-
ATW
Nonstop1h 04m
American Airlines
Deal found 3/10$234
This Delta deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/171:26 pm
ATW
-
ORD
1 stop5h 15m
Delta
Thu 6/258:55 am
ORD
-
ATW
1 stop3h 51m
Delta
Deal found 3/9$239
This American Airlines deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/196:39 pm
ATW
-
ORD
Nonstop1h 20m
American Airlines
Fri 3/2711:45 am
ORD
-
ATW
Nonstop1h 04m
American Airlines
Deal found 3/8$244
This Delta deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/21:26 pm
ATW
-
MDW
1 stop5h 05m
Delta
Mon 9/71:00 pm
MDW
-
ATW
1 stop3h 37m
Delta
Deal found 3/8$249
This Delta deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/171:26 pm
ATW
-
ORD
1 stop5h 15m
Delta
Sun 7/197:10 am
ORD
-
ATW
1 stop5h 36m
Delta
Deal found 3/6$249
This Delta deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/287:00 am
ATW
-
ORD
1 stop6h 01m
Delta
Mon 6/16:24 am
ORD
-
ATW
1 stop5h 27m
Delta
Deal found 3/9$254

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 March 10, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$199
(American Airlines)

One-way from

$126
(Kiwi.com)

Popular in

November

Cheapest in

February

Average price

$230
Provider with most accurate pricing for Appleton Intl-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Appleton Intl-Chicago (CHI) flights.
Search Deals
From Oshkosh to Chicago (CHI)
Search Deals
One-way flight from Oshkosh to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 19% potential increase in price ($57 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
Search Deals

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 March 10, 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

Price

Cheapest round-trip

AppletonChicago

ATW - MDW

ATWMDW

Appleton Intl

Fri 4/3

7:00 am-12:29 pm

1 stop5h 29m

Chicago Midway

Fri 4/10

1:10 pm-5:42 pm

1 stop4h 32m

$219

AppletonChicago

ATW - MDW

ATWMDW

Appleton Intl

Wed 5/20

7:00 am-12:42 pm

1 stop5h 42m

Chicago Midway

Sat 5/23

7:13 pm-10:54 pm

1 stop3h 41m

$219

AppletonChicago

ATW - ORD

ATWORD

Appleton Intl

Sat 8/15

12:06 pm-4:48 pm

1 stop4h 42m

Chicago O'Hare Intl

Sat 8/29

10:35 am-4:37 pm

1 stop6h 02m

$219

AppletonChicago

ATW - ORD

ATWORD

Appleton Intl

Thu 5/7

12:32 pm-7:20 pm

1 stop6h 48m

Chicago O'Hare Intl

Sun 5/10

6:24 am-11:51 am

1 stop5h 27m

$219

AppletonChicago

ATW - ORD

ATWORD

Appleton Intl

Wed 6/17

1:26 pm-6:41 pm

1 stop5h 15m

Chicago O'Hare Intl

Wed 6/24

8:55 am-12:46 pm

1 stop3h 51m

$219

AppletonChicago

ATW - ORD

ATWORD

Appleton Intl

Fri 4/3

7:00 am-1:17 pm

1 stop6h 17m

Chicago O'Hare Intl

Fri 4/10

1:57 pm-5:42 pm

1 stop3h 45m

$249

AppletonChicago

ATW - ORD

ATWORD

Appleton Intl

Fri 7/17

1:26 pm-6:41 pm

1 stop5h 15m

Chicago O'Hare Intl

Sun 7/19

7:10 am-12:46 pm

1 stop5h 36m

$249
Quickest round-trip

AppletonChicago

ATW - ORD

ATWORD

Appleton Intl

Sat 4/18

3:46 pm-5:05 pm

Nonstop1h 19m

Chicago O'Hare Intl

Wed 4/22

10:45 am-11:58 am

Nonstop1h 13m

$259

AppletonChicago

ATW - ORD

ATWORD

Appleton Intl

Wed 9/2

10:55 am-4:36 pm

1 stop5h 41m

Chicago O'Hare Intl

Mon 9/7

8:55 am-12:46 pm

1 stop3h 51m

$288

AppletonChicago

ATW - MDW

ATWMDW

Appleton Intl

Thu 4/2

7:00 am-12:29 pm

1 stop5h 29m

Chicago Midway

Thu 4/9

1:10 pm-5:30 pm

1 stop4h 20m

$289

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/7

Showing 1-10 of 35 resultsSorted by cheapest first
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4

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.
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

What is the cheapest month to book a flight from Oshkosh to Chicago?

Currently, January is the cheapest month in which you can book a flight from Oshkosh to Chicago (average of $179). Flying from Oshkosh to Chicago in September is currently the most expensive (average of $182). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from 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 March 10, 2026.

Unlike in the evening, when flights are generally more expensive, you can save up to 22% 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 February 21, 2026.

Travelers seeking maximum savings on their Oshkosh to Chicago flight should consider departing on Thursday 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 March 10, 2026.

The most flights from OS9 to CHI are scheduled on a Monday (59 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (33 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 March 10, 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.
United Airlines
7.4
Good
9,409 reviews

Boarding

7.7

Comfort

7.3

Food

6.6

Crew

8.1

Overall

7.4

Entertainment

7.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
United Airlines
7.4
Good
9,409 reviews
United Airlines
7.4
Good
9,409 reviews

Boarding

7.7

Comfort

7.3

Food

6.6

Crew

8.1

Overall

7.4

Entertainment

7.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
American Airlines
7.1
Good
11,413 reviews
United Airlines
7.4
Good
9,409 reviews

Boarding

7.7

Comfort

7.3

Food

6.6

Crew

8.1

Overall

7.4

Entertainment

7.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.

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.

  • How long is the flight from Oshkosh to Chicago?

    A quick flight from Oshkosh to Chicago can take about 5h 29m. Delta provides one of the quickest options available for as low as $219. The distance between Oshkosh and Chicago is about 175 mi.

  • What are the most reliable airlines from Oshkosh to Chicago?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Oshkosh to Chicago on time: Republic Airways (100%), PSA Airlines (81%), United Airlines (74%).

  • What are the cheapest flights from Oshkosh to Chicago?

    While on average a flight from Oshkosh to Chicago is generally $880, our data shows the cheapest flight currently is $124. When looking at the most popular route, (Appleton Intl - Chicago O'Hare Intl), you can expect to pay $199 for that flight.

  • Can I find deals for flights from Oshkosh to Chicago that include hotel bookings?

    Yes. In addition to deals on Oshkosh to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Oshkosh to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Oshkosh to Chicago.

  • Can I find deals for business class flights from Oshkosh to Chicago?

    Yes. Cheapflights offers flight deals from Oshkosh to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Oshkosh to Chicago?

    Currently, January is the cheapest month in which you can book a flight from Oshkosh to Chicago (average of $179). Flying from Oshkosh to Chicago in September is currently the most expensive (average of $182). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

Browse thousands of different options on Cheapflights for your next trip

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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 March 10, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$179Average$259FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$179Average$262FlexibilityNo cancel feeOn-time69%

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