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Cheap flights from Oshkosh, WI to Chicago (CHI)

MKE — CHI
Oct 27 — Nov 31
Tue 10/27
Tue 11/3
1 adult, Economy
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Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Popular in

September

Cheapest in

February

Average price

$388
Provider with most accurate pricing for Appleton Intl-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Appleton Intl-Chicago (CHI) flights.
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Highest demand for flights based on searches. 5% potential increase in price ($19 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in September 2026
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Cheapflights Insights

Everything you need to know about your flight from Oshkosh to Chicago

What is the cheapest time of day to fly from OS9 to CHI?

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?

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

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
10,242 reviews

Crew

8.1

Boarding

7.7

Food

6.7

Overall

7.4

Comfort

7.3

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Chris,Aug 2026

MIA - ORD

Had to go through TSA again, already purchased bottle drink. TSA would not let through, United changed gates last minute. This experience bad for everyone. Staff rude, not our fault. Staff from Chicago to Wichita excellent!
United Airlines
7.4
Good
10,242 reviews
United Airlines
7.4
Good
10,242 reviews

Crew

8.1

Boarding

7.7

Food

6.7

Overall

7.4

Comfort

7.3

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Chris,Aug 2026

MIA - ORD

Had to go through TSA again, already purchased bottle drink. TSA would not let through, United changed gates last minute. This experience bad for everyone. Staff rude, not our fault. Staff from Chicago to Wichita excellent!
American Airlines
7.0
Good
12,099 reviews
United Airlines
7.4
Good
10,242 reviews

Crew

8.1

Boarding

7.7

Food

6.7

Overall

7.4

Comfort

7.3

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Chris,Aug 2026

MIA - ORD

Had to go through TSA again, already purchased bottle drink. TSA would not let through, United changed gates last minute. This experience bad for everyone. Staff rude, not our fault. Staff from Chicago to Wichita excellent!

Related info for your journey

  • 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 (92%), Japan Airlines (79%), Envoy Air (74%).

  • What are the cheapest flights from Oshkosh to Chicago?

    While on average a flight from Oshkosh to Chicago is generally $748, our data shows the cheapest flight currently is $144. When looking at the most popular route, (Appleton Intl - Chicago O'Hare Intl), you can expect to pay $289 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.

See more FAQs

Traveling to a place near Chicago?

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

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Top 2 airlines flying from Oshkosh to Chicago

AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$171Average$275FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$179Average$292FlexibilityNo cancel feeOn-time71%

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