Weekly flight availability from Oshkosh to Chicago O'Hare Intl Airport

The most flights from OS9 to ORD are scheduled on a Friday (59 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (40 on average).

In terms of precipitation, rainfall in Chicago O'Hare Intl Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago O'Hare Intl Airport when rainfall is around 1.7 in.

If weather is an important factor for your trip to Chicago O'Hare Intl Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

What are the cheapest flights from Oshkosh to Chicago O'Hare Intl Airport?

While on average a flight from Oshkosh to Chicago O'Hare Intl Airport 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.

What are the most reliable airlines from Oshkosh to Chicago O'Hare Intl Airport?

Before booking your flight to Chicago O'Hare Intl Airport from Oshkosh, check out the most reliable airlines to get you to your destination on time: Republic Airways (92%), Japan Airlines (79%), Envoy Air( 74%).

Can I find deals for flights from Oshkosh to O'Hare Intl that include hotel bookings?

Yes. In addition to deals on Oshkosh to O'Hare Intl flights, Cheapflights offers vacation packages that include both flights and hotel.

How can I find direct flights from Oshkosh to O'Hare Intl?

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

Can I find deals for business class flights from Oshkosh to O'Hare Intl?

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

Find Cheap Flights from Oshkosh to Chicago O'Hare Intl Airport

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Most accurate provider	FlightHub 3 stars
Most trusted provider	FlightHub 3 stars
Popular in	August
Cheapest in	November
Average price	$309

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. 10% potential increase in price ($33 potential increase over avg. RT price).

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Cheapest flight prices on average. 3% potential price decrease ($10 potential savings vs. average RT price).

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Average for round-trip flights in September 2026

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Everything you need to know about your flight from Oshkosh to Chicago O'Hare Intl Airport

Prices

Airlines

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

It’s typically best to fly out from Oshkosh to Chicago O'Hare Intl Airport in the morning. Doing so could potentially save you 22% on the flight price compared to flying in the evening, which is usually more expensive.

What is the cheapest day to fly from Oshkosh to Chicago O'Hare Intl Airport?

Travelers seeking maximum savings on their Oshkosh to Chicago O'Hare Intl Airport 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 O'Hare Intl

See what other customers who have flown with United Airlines and American Airlines from Oshkosh to Chicago O'Hare Intl Airport have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.

United Airlines

7.4

Good

10,242 reviews

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

Reviews

1 / 20

4.0

Okay

Chris,Aug 2026

MIA - ORD

American Airlines

7.0

Good

12,099 reviews

United Airlines

7.4

Good

10,242 reviews

Reviews

1 / 20

4.0

Okay

Chris,Aug 2026

MIA - ORD

Related info for your journey

What are the most reliable airlines from Oshkosh to Chicago O'Hare Intl Airport?
Before booking your flight to Chicago O'Hare Intl Airport from Oshkosh, check out the most reliable airlines to get you to your destination on time: Republic Airways (92%), Japan Airlines (79%), Envoy Air( 74%).
What are the cheapest flights from Oshkosh to Chicago O'Hare Intl Airport?
While on average a flight from Oshkosh to Chicago O'Hare Intl Airport 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 O'Hare Intl that include hotel bookings?
Yes. In addition to deals on Oshkosh to O'Hare Intl flights, Cheapflights offers vacation packages that include both flights and hotel.
How can I find direct flights from Oshkosh to O'Hare Intl?
After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Oshkosh to O'Hare Intl.
Can I find deals for business class flights from Oshkosh to O'Hare Intl?
Yes. Cheapflights offers flight deals from Oshkosh to O'Hare Intl by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

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Top 2 airlines flying from Oshkosh to O'Hare Intl

Airline	Cheapest	Average	Flexibility	On-time
United Airlines	Cheapest$171	Average$275	FlexibilityNo cancel fee	On-time69%
American Airlines	Cheapest$179	Average$292	FlexibilityNo cancel fee	On-time71%

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Cheap flights from Oshkosh, WI to O'Hare Intl (ORD)

Find cheap flights from Oshkosh to O'Hare Intl with Cheapflights

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3. Compare prices and book

Find flight deals from Oshkosh to O'Hare Intl

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Popular in

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Average price

Cheapflights Insights

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

It’s typically best to fly out from Oshkosh to Chicago O'Hare Intl Airport in the morning. Doing so could potentially save you 22% on the flight price compared to flying in the evening, which is usually more expensive.

What is the cheapest day to fly from Oshkosh to Chicago O'Hare Intl Airport?

Travelers seeking maximum savings on their Oshkosh to Chicago O'Hare Intl Airport 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.

Weekly flight availability from Oshkosh to Chicago O'Hare Intl Airport

The most flights from OS9 to ORD are scheduled on a Friday (59 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (40 on average).

Reviews of airlines servicing O'Hare Intl

See what other customers who have flown with United Airlines and American Airlines from Oshkosh to Chicago O'Hare Intl Airport have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.

Related info for your journey

What are the most reliable airlines from Oshkosh to Chicago O'Hare Intl Airport?

What are the cheapest flights from Oshkosh to Chicago O'Hare Intl Airport?

Can I find deals for flights from Oshkosh to O'Hare Intl that include hotel bookings?

How can I find direct flights from Oshkosh to O'Hare Intl?

Can I find deals for business class flights from Oshkosh to O'Hare Intl?

Traveling to a place near Chicago O'Hare Intl Airport?

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Complete your trip to O'Hare Intl by adding a car rental and/or hotel reservation to your travel itinerary.

Search flights from Oshkosh to O'Hare Intl by cabin class

Find flights from Oshkosh to O'Hare Intl, based on your preferred cabin class, be it economy, premium economy, business, or first class.

Other flights to O'Hare Intl

Explore flights to O'Hare Intl departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on September 27, 2026.

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