$160 Cheap Flights from Tupelo (TUP) to Chicago (ORD)

View $160 flight on Tue, Jan 27, 2026Opens in a new window

Popular airlines from Tupelo, MS (TUP-Tupelo Regional) to Chicago O'Hare Intl. Airport (ORD)

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Cheap Flights from Tupelo to Chicago (TUP-ORD)

Prices were available within the past 7 days and start at $160 for one-way flights and $298 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Contour Airlines
Mon, Jan 12 - Tue, Jan 13
TUP
Tupelo
ORD
Chicago
$298 Roundtrip, found 2 days ago
$298
Roundtrip
found 2 days ago
Select Contour Airlines flight, departing Mon, Jan 12 from Tupelo to Chicago, returning Tue, Jan 13, priced at $298 found 2 days ago
Contour Airlines
Mon, Jan 12 - Sun, Jan 18
TUP
Tupelo
ORD
Chicago
$320 Roundtrip, found 2 days ago
$320
Roundtrip
found 2 days ago
Select Contour Airlines flight, departing Mon, Jan 12 from Tupelo to Chicago, returning Sun, Jan 18, priced at $320 found 2 days ago
Contour Airlines
Mon, Jan 12 - Thu, Jan 15
TUP
Tupelo
ORD
Chicago
$330 Roundtrip, found 2 days ago
$330
Roundtrip
found 2 days ago
Select Contour Airlines flight, departing Mon, Jan 12 from Tupelo to Chicago, returning Thu, Jan 15, priced at $330 found 2 days ago
Contour Airlines
Sat, Jan 10 - Tue, Jan 13
TUP
Tupelo
ORD
Chicago
$331 Roundtrip, found 2 days ago
$331
Roundtrip
found 2 days ago
Select Contour Airlines flight, departing Sat, Jan 10 from Tupelo to Chicago, returning Tue, Jan 13, priced at $331 found 2 days ago
Contour Airlines
Thu, Dec 25 - Mon, Jan 5
TUP
Tupelo
ORD
Chicago
$340 Roundtrip, found 2 days ago
$340
Roundtrip
found 2 days ago
Select Contour Airlines flight, departing Thu, Dec 25 from Tupelo to Chicago, returning Mon, Jan 5, priced at $340 found 2 days ago
Contour Airlines
Thu, Dec 25 - Sun, Jan 4
TUP
Tupelo
ORD
Chicago
$347 Roundtrip, found 3 days ago
$347
Roundtrip
found 3 days ago
Select Contour Airlines flight, departing Thu, Dec 25 from Tupelo to Chicago, returning Sun, Jan 4, priced at $347 found 3 days ago
Contour Airlines
Sat, Jan 10 - Sun, Jan 18
TUP
Tupelo
ORD
Chicago
$353 Roundtrip, found 2 days ago
$353
Roundtrip
found 2 days ago
Select Contour Airlines flight, departing Sat, Jan 10 from Tupelo to Chicago, returning Sun, Jan 18, priced at $353 found 2 days ago
Contour Airlines
Tue, Mar 3 - Sun, Mar 8
TUP
Tupelo
ORD
Chicago
$358 Roundtrip, found 23 hours ago
$358
Roundtrip
found 23 hours ago
Select Contour Airlines flight, departing Tue, Mar 3 from Tupelo to Chicago, returning Sun, Mar 8, priced at $358 found 23 hours ago
Contour Airlines
Mon, Mar 2 - Sun, Mar 8
TUP
Tupelo
ORD
Chicago
$359 Roundtrip, found 23 hours ago
$359
Roundtrip
found 23 hours ago
Select Contour Airlines flight, departing Mon, Mar 2 from Tupelo to Chicago, returning Sun, Mar 8, priced at $359 found 23 hours ago
Contour Airlines
Sat, Jan 10 - Thu, Jan 15
TUP
Tupelo
ORD
Chicago
$363 Roundtrip, found 2 days ago
$363
Roundtrip
found 2 days ago
Select Contour Airlines flight, departing Sat, Jan 10 from Tupelo to Chicago, returning Thu, Jan 15, priced at $363 found 2 days ago

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $408
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $408
Flights from Tupelo (TUP) to Chicago (ORD)
Origin airport
Tupelo Regional
Destination airport
O'Hare Intl.
Airlines serving
Contour Airlines
Roundtrip price
$298
Distance
534 mi

Tupelo to Chicago Flights

The cheapest times to fly from Tupelo 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 Tupelo to Chicago are during the month of January. You can find some of the cheapest flights from Tupelo to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Tupelo to Chicago

Sunday is one of the best days to book for cheap flights from Tupelo 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 Tupelo 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 Tupelo to Chicago in 2026. You can also book with separate airlines for your outbound and return journeys, from $160 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 Tupelo 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 Tupelo 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 Tupelo Regional Airport (TUP) to O'Hare Intl. Airport (ORD) cost?
Secure a cheap one-way flight from $160 or cheap return flight from $298 from Tupelo Regional Airport (TUP) to O'Hare Intl. Airport (ORD) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight offers on this route.
What is the cheapest month to fly from Tupelo Regional Airport (TUP) to O'Hare Intl. Airport (ORD)?
The cheapest month to fly from TUP to ORD is January, when there's less demand. Off-peak season is generally when you'll find lower airfares between these airports.
What is the cheapest airline that flies from Tupelo Regional Airport (TUP) to O'Hare Intl. Airport (ORD)?
Expedia's filter tool lets you easily compare different airlines, departure times and fares all in one place. Tailor the search to your trip, then sort by "Price (lowest to highest)" to find out which carrier offers the cheapest TUP to ORD flight.
How many flights per day from Tupelo Regional Airport (TUP) to O'Hare Intl. Airport (ORD)?
You'll need to hop on a flight with a layover when traveling from Tupelo Regional Airport (TUP) to O'Hare Intl. Airport (ORD). Direct flights don't operate daily on this route. However, simply filter your search to include one or two stops to discover an option that works for you.
What day of the week has the most flights from TUP to ORD?
You'll generally find Tuesday the quietest day for flights, while Fridays are often the busiest.* However this can vary 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 Tupelo Regional Airport (TUP) to O'Hare Intl. Airport (ORD)?
To avoid possible delays on the Tupelo Regional Airport (TUP) to O'Hare Intl. Airport (ORD) route, aim to fly before 3 PM. Flights after this time are 22% more likely to be canceled.**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 Tupelo Regional Airport (TUP) to O'Hare Intl. Airport (ORD) last-minute?
Last-minute fares from TUP to ORD are typically more expensive. For the lowest rates, start looking for flights ahead of time. That said, if you're flexible with your travel dates, you may score a cheap fare right before you leave.
Is it cheaper to book a TUP to ORD flight and hotel package?
You can save money by booking a TUP to ORD flight and hotel package compared to booking separately. In fact, you could save hundreds of dollars by bundling with Expedia. And it's simple to manage everything in one convenient place. After choosing your ideal accommodations and flights, consider other add-ons like activities, tours and car rentals.
Can I cancel or change the date of my flight from Tupelo Regional Airport (TUP) to O'Hare Intl. Airport (ORD)?
Usually, it's possible to reschedule or cancel your TUP to ORD flight. However, if the booking was made more than 24 hours ago, additional fees may apply. Refer to your airline's policies in your itinerary to see what changes are possible and if any costs are involved. You'll also find further details on our Customer Service portal.

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*Available to One Key members.