O'Hare Intl

$184+ Cheap flights from Oshkosh, WI to O'Hare Intl (ORD)

MKE — ORD
Dec 13 — Dec 201
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1. Tell us where you want to go

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Cheap flight deals from Oshkosh to O'Hare Intl

Cheapest flights from Oshkosh to O'Hare Intl

Sat 12/126:25 pm -
Nonstop1h 34m
Wed 12/234:39 pm -
Nonstop1h 16m
Deal found 11/11$319
Wed 12/166:15 am -
Nonstop1h 40m
Sat 12/199:50 pm -
Nonstop1h 24m
Deal found 11/10$333
Mon 11/234:55 pm -
Nonstop1h 42m
Mon 1/49:50 pm -
Nonstop1h 25m
Deal found 11/8$334
Fri 12/45:39 pm -
1 stop3h 56m
Sat 12/53:47 pm -
1 stop6h 10m
Deal found 11/8$339
Tue 12/295:30 am -
Nonstop1h 36m
Sat 1/24:39 pm -
Nonstop1h 16m
Deal found 11/11$343
Fri 11/279:50 am -
Nonstop1h 37m
Mon 11/3010:00 pm -
Nonstop1h 17m
Deal found 11/10$349
Sat 12/1911:30 am -
Nonstop1h 21m
Sun 12/204:39 pm -
Nonstop1h 16m
Deal found 11/11$350
Thu 12/35:39 pm -
1 stop3h 56m
Sat 12/56:20 am -
1 stop5h 39m
Deal found 11/8$354
Mon 12/74:02 pm -
2 stops22h 28m
Wed 12/165:24 pm -
1 stop29h 26m
Deal found 11/9$357
Thu 11/265:35 am -
Nonstop1h 37m
Sat 11/2811:00 pm -
Nonstop1h 09m
Deal found 11/12$359

Find flight deals from Oshkosh to O'Hare Intl

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$319
(United Airlines)

One-way from

$184
(United Airlines)

Popular in

November

Cheapest in

January

Average price

$511
Provider with most accurate pricing for Appleton Intl-Chicago (CHI) flight deals.
Provider most trusted by Cheapflights users for Appleton Intl-Chicago (CHI) flights.
From Oshkosh to Chicago O'Hare Intl
One-way flight from Oshkosh to Chicago O'Hare Intl
Highest demand for flights based on searches. 10% potential increase in price ($35 potential increase over avg. RT price).
Cheapest flight prices on average. 6% potential price decrease ($19 potential savings vs. average RT price).
Average for round-trip flights in November 2026

Cheapflights Fare Finder

 
Use the filters below to find and compare flights from Oshkosh to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

AppletonChicago

ATW Appleton Intl - ORD Chicago O'Hare Intl

ATWORD

Appleton Intl

Sat 12/26

8:00 am-9:45 am

Nonstop1h 45m

Chicago O'Hare Intl

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$184

AppletonChicago

ATW Appleton Intl - ORD Chicago O'Hare Intl

ATWORD

Appleton Intl

Mon 3/1

6:00 am-7:40 am

Nonstop1h 40m

Chicago O'Hare Intl

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$214

AppletonChicago

ATW Appleton Intl - ORD Chicago O'Hare Intl

ATWORD

Appleton Intl

Mon 3/1

5:28 pm-9:32 pm

1 stop4h 04m

Chicago O'Hare Intl

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$224

AppletonChicago

ATW Appleton Intl - ORD Chicago O'Hare Intl

ATWORD

Appleton Intl

Tue 12/1

6:17 pm-7:55 pm

Nonstop1h 38m

Chicago O'Hare Intl

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$239
Quickest round-trip

AppletonChicago

ATW Appleton Intl - ORD Chicago O'Hare Intl

ATWORD

Appleton Intl

Thu 12/10

2:39 pm-4:00 pm

Nonstop1h 21m

Chicago O'Hare Intl

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$245

AppletonChicago

ATW Appleton Intl - ORD Chicago O'Hare Intl

ATWORD

Appleton Intl

Tue 12/1

8:00 am-9:41 am

Nonstop1h 41m

Chicago O'Hare Intl

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$274

AppletonChicago

ATW Appleton Intl - ORD Chicago O'Hare Intl

ATWORD

Appleton Intl

Mon 3/1

6:30 am-4:55 pm

2 stops34h 25m

Chicago O'Hare Intl

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$280

AppletonChicago

ATW Appleton Intl - ORD Chicago O'Hare Intl

ATWORD

Appleton Intl

Sat 12/26

6:45 am-12:46 pm

1 stop6h 01m

Chicago O'Hare Intl

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$304

AppletonChicago

ATW Appleton Intl - ORD Chicago O'Hare Intl

ATWORD

Appleton Intl

Thu 12/24

8:00 am-9:45 am

Nonstop1h 45m

Chicago O'Hare Intl

Wed 12/30

12:50 pm-2:15 pm

Nonstop1h 25m

$319

AppletonChicago

ATW Appleton Intl - ORD Chicago O'Hare Intl

ATWORD

Appleton Intl

Mon 12/7

9:54 am-11:31 am

Nonstop1h 37m

Chicago O'Hare Intl

Wed 12/16

10:46 am-12:02 pm

Nonstop1h 16m

$319

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/8

Showing 1-10 of 21 resultsSorted by cheapest first
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Best time to book a flight from Oshkosh to O'Hare Intl

Have a flexible travel schedule? Discover the best time to fly to O'Hare Intl from Oshkosh with our price prediction graph.
Estimated round-trip price

Cheapflights Insights

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

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 12% on the flight price compared to flying in the evening, which is usually more expensive.

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

The most flights from OS9 to ORD are scheduled on a Wednesday (56 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (30 on average).

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 Sunday 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.

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.

Overall

7.3

Boarding

7.7

Food

6.7

Comfort

7.3

Crew

8.1

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!

Overall

7.3

Boarding

7.7

Food

6.7

Comfort

7.3

Crew

8.1

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!

Overall

7.3

Boarding

7.7

Food

6.7

Comfort

7.3

Crew

8.1

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

  • How long is the flight from Oshkosh to Chicago O'Hare Intl Airport?

    Airlines like United Airlines fly from Oshkosh to Chicago O'Hare Intl Airport in about 1h 45m. The time it takes to get you to your destination is usually consistent. The distance between Oshkosh and Chicago O'Hare Intl Airport is about 160 mi. All flights are typically nonstop.

  • 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: Porter Airlines (94%), Republic Airways (83%), Copa Airlines( 80%).

  • 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 $1,004, 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 $319 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.

See more FAQs

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

Book flights to Chicago O'Hare Intl Airport if you plan to visit one of these locations
Benton Harbor
Rosemont
Naperville
Lake Geneva
Des Plaines
Glenview
Oak Brook
Aurora
Oakbrook Terrace
Delavan
Schaumburg
Libertyville
Rockford
Hoffman Estates
Gurnee
Orland Park
South Holland
Beloit
Elgin
Racine

Browse thousands of different options on Cheapflights for your next trip

Top 2 airlines flying from Oshkosh to O'Hare Intl

AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$171Average$294FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$179Average$327FlexibilityNo cancel feeOn-time71%

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