$332 Cheap Flights from Sheridan (SHR) to Chicago (ORD)

View $332 flight on Wed, Sep 10, 2025Opens in a new window

Popular airlines from Sheridan, WY (SHR-Sheridan County) to Chicago O'Hare Intl. Airport (ORD)

Cheap Flights from Sheridan to Chicago (SHR-ORD)

Prices were available within the past 7 days and start at $332 for one-way flights and $318 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

United
Tue, Jan 13 - Fri, Jan 30
SHR
Sheridan
ORD
Chicago
$318 Roundtrip, found 1 day ago
$318
Roundtrip
found 1 day ago
Select United flight, departing Tue, Jan 13 from Sheridan to Chicago, returning Fri, Jan 30, priced at $318 found 1 day ago
United
Tue, Jan 13 - Tue, Jan 27
SHR
Sheridan
ORD
Chicago
$364 Roundtrip, found 1 day ago
$364
Roundtrip
found 1 day ago
Select United flight, departing Tue, Jan 13 from Sheridan to Chicago, returning Tue, Jan 27, priced at $364 found 1 day ago
United
Tue, Jan 13 - Wed, Jan 28
SHR
Sheridan
ORD
Chicago
$383 Roundtrip, found 1 day ago
$383
Roundtrip
found 1 day ago
Select United flight, departing Tue, Jan 13 from Sheridan to Chicago, returning Wed, Jan 28, priced at $383 found 1 day ago
United
Tue, Oct 28 - Sat, Nov 8
SHR
Sheridan
ORD
Chicago
$387 Roundtrip, found 2 days ago
$387
Roundtrip
found 2 days ago
Select United flight, departing Tue, Oct 28 from Sheridan to Chicago, returning Sat, Nov 8, priced at $387 found 2 days ago
United
Tue, Jan 20 - Fri, Jan 30
SHR
Sheridan
ORD
Chicago
$390 Roundtrip, found 2 days ago
$390
Roundtrip
found 2 days ago
Select United flight, departing Tue, Jan 20 from Sheridan to Chicago, returning Fri, Jan 30, priced at $390 found 2 days ago
United
Mon, Jan 12 - Fri, Jan 30
SHR
Sheridan
ORD
Chicago
$394 Roundtrip, found 1 day ago
$394
Roundtrip
found 1 day ago
Select United flight, departing Mon, Jan 12 from Sheridan to Chicago, returning Fri, Jan 30, priced at $394 found 1 day ago
United
Tue, Oct 21 - Tue, Oct 28
SHR
Sheridan
ORD
Chicago
$397 Roundtrip, found 6 days ago
$397
Roundtrip
found 6 days ago
Select United flight, departing Tue, Oct 21 from Sheridan to Chicago, returning Tue, Oct 28, priced at $397 found 6 days ago
United
Sat, Jan 17 - Tue, Jan 27
SHR
Sheridan
ORD
Chicago
$409 Roundtrip, found 1 day ago
$409
Roundtrip
found 1 day ago
Select United flight, departing Sat, Jan 17 from Sheridan to Chicago, returning Tue, Jan 27, priced at $409 found 1 day ago
United
Wed, Jan 21 - Fri, Feb 6
SHR
Sheridan
ORD
Chicago
$412 Roundtrip, found 1 day ago
$412
Roundtrip
found 1 day ago
Select United flight, departing Wed, Jan 21 from Sheridan to Chicago, returning Fri, Feb 6, priced at $412 found 1 day ago
United
Sun, Feb 15 - Thu, Mar 5
SHR
Sheridan
ORD
Chicago
$421 Roundtrip, found 2 days ago
$421
Roundtrip
found 2 days ago
Select United flight, departing Sun, Feb 15 from Sheridan to Chicago, returning Thu, Mar 5, priced at $421 found 2 days ago
Flights from Sheridan (SHR) to Chicago (ORD)
Origin airport
Sheridan County
Destination airport
O'Hare Intl.
Airlines serving
United
Roundtrip price
$318
Distance
974 mi

Sheridan to Chicago Flights

The cheapest times to fly from Sheridan to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Sheridan to Chicago are during the month of January. You can find some of the cheapest flights from Sheridan to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Sheridan to Chicago

Sunday is one of the best days to book for cheap flights from Sheridan to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Sheridan to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Sheridan to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $332 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Sheridan to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Sheridan to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from Sheridan, WY (SHR-Sheridan County) to O'Hare Intl. Airport (ORD) cost?
Snag a cheap one-way flight from $332 or cheap return flight from $318 from Sheridan, WY (SHR-Sheridan County) to O'Hare Intl. Airport (ORD) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight deals on this route.
What is the cheapest month to fly from Sheridan, WY (SHR-Sheridan County) to O'Hare Intl. Airport (ORD)?
The cheapest month to fly from SHR to ORD is January, when there's less demand. Off-peak season is typically when airlines offer lower prices between these airports.
What is the cheapest airline that flies from Sheridan, WY (SHR-Sheridan County) to O'Hare Intl. Airport (ORD)?
Expedia's filter tool lets you easily compare different airlines, flight durations and fares all in one place. Select your preferences, then sort by "Price (lowest to highest)" to see which carrier offers the cheapest SHR to ORD flight.
How many flights per day from Sheridan, WY (SHR-Sheridan County) to O'Hare Intl. Airport (ORD)?
There are no daily direct flights from Sheridan, WY (SHR-Sheridan County) to O'Hare Intl. Airport (ORD). But you can opt for flights with layovers. Filter your search results on Expedia to include one or more stops, and you'll be soaring above the clouds in no time at all.
What day of the week has the most flights from SHR to ORD?
You'll usually find Tuesday the quietest day for flights, while Fridays tend to be the busiest.* However this can change from season to season and during public holidays or peak travel times.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Sheridan, WY (SHR-Sheridan County) to O'Hare Intl. Airport (ORD)?
Select a flight from Sheridan, WY (SHR-Sheridan County) to O'Hare Intl. Airport (ORD) that leaves before 3 PM to reduce the risk of delays and cancellations. Departures after this time have a 22% higher chance of being canceled, on average.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
Is it cheaper to buy a plane ticket from Sheridan, WY (SHR-Sheridan County) to O'Hare Intl. Airport (ORD) last-minute?
Waiting until just before your trip to book your flight from SHR to ORD generally means paying more. While it's possible to find some last-minute deals, they aren't always guaranteed. Be flexible with your itinerary for the best chance of scoring a bargain.
Is it cheaper to book a SHR to ORD flight and hotel package?
Compared with arranging flights and hotels separately, booking a SHR to ORD flight and hotel package with Expedia could lead to significant savings. Better yet, managing everything in one place will take the hassle out of planning your trip. Just pick your flights and choose from our wide range of hotels, then tailor your trip with extras like car rentals and activities.
Can I cancel or change the date of my flight from Sheridan, WY (SHR-Sheridan County) to O'Hare Intl. Airport (ORD)?
If you reserved your SHR to ORD flight in the last 24 hours, you may be able to cancel or modify it at no cost. Depending on the airline and the ticket type you purchased, additional charges may apply for changes after that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal for further details.

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*Available to One Key members.