Title: Cheap Flights from Tupelo to Chicago (TUP to ORD) - Expedia.co.uk ![City of Chicago. Image of Chicago downtown and Chicago River with bridges at sunny summer day](https://images.trvl-media.com/place/178248/e6aa83ce-7ad8-43a5-9d1d-b055eefa7e78.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/178248/e6aa83ce-7ad8-43a5-9d1d-b055eefa7e78.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Cheap Flights from Tupelo (TUP) to Chicago (ORD) - [Return](?flightType=roundtrip) - [One-way](?flightType=oneway) - [Multi-city](?flightType=multicity) ### Travellers Adults ChildrenAges 2 to 17 InfantsYounger than 2 EconomyPremium economyBusiness classFirst class Leaving from Going to Departing Returning Add a place to stay Add a car Direct flights only ## Popular airlines from Tupelo, MS (TUP-Tupelo Regional) to Chicago O'Hare International Airport (ORD) - ![British Airways](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_BA.svg) British Airways [](https://www.expedia.co.uk/Flights-Search?leg1=from:tup,to:ord,departure:06/10/2025TANYT&leg2=from:ord,to:tup,departure:13/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"BA"}}]) - ![easyJet](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_U2.svg) easyJet [](https://www.expedia.co.uk/Flights-Search?leg1=from:tup,to:ord,departure:06/10/2025TANYT&leg2=from:ord,to:tup,departure:13/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"U2"}}]) - ![Lufthansa](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_LH.svg) Lufthansa [](https://www.expedia.co.uk/Flights-Search?leg1=from:tup,to:ord,departure:06/10/2025TANYT&leg2=from:ord,to:tup,departure:13/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"LH"}}]) - ![Ryanair](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_FR.svg) Ryanair [](https://www.expedia.co.uk/Flights-Search?leg1=from:tup,to:ord,departure:06/10/2025TANYT&leg2=from:ord,to:tup,departure:13/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"FR"}}]) - ![American Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AA.svg) American Airlines [](https://www.expedia.co.uk/Flights-Search?leg1=from:tup,to:ord,departure:06/10/2025TANYT&leg2=from:ord,to:tup,departure:13/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AA"}}]) - ![Jet2](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_LS.svg) Jet2 [](https://www.expedia.co.uk/Flights-Search?leg1=from:tup,to:ord,departure:06/10/2025TANYT&leg2=from:ord,to:tup,departure:13/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"LS"}}]) - ![Swiss International Air Lines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_LX.svg) Swiss International Air Lines [](https://www.expedia.co.uk/Flights-Search?leg1=from:tup,to:ord,departure:06/10/2025TANYT&leg2=from:ord,to:tup,departure:13/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"LX"}}]) ![notification illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__notification.svg) ### Be in the know Get alerts if flight prices drop or rise\* ![deals illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Book smarter Save up to 25% on select hotels after you book a flight\* ![trophy illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__trophy.svg) ### Earn twice Earn your airline miles on top of our rewards [Sign in](https://www.expedia.co.uk/login) ## Frequently asked questions ### How much is a flight from Tupelo Regional Airport (TUP) to O'Hare Airport? > If you're planning on travelling from TUP to ORD, round-trip journeys start from . This figure is based on airfares available within the last 7 days on Expedia for flights departing within the next year, so don't delay. Book now and save yourself both money and time. Prices and availability are subject to change. Additional terms apply. ### Do I need to pay a cancellation fee if I cancel my flight from Tupelo Regional Airport to O'Hare Intl. Airport (ORD)? > The majority of flights can be cancelled online, but every air carrier has its own terms and conditions. If you do decide to cancel your flight, check out our [Customer Service Portal](https://www.expedia.co.uk/service/?langid=1033) and follow the instructions. ### How do I find cheap flights from Tupelo Regional Airport to ORD that have flexible change policies? > Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you're searching for TUP to ORD flights, you'll see a "no change fees" filter for you to select. ### How far is the flight from Tupelo Regional Airport (TUP) to O'Hare Intl. Airport (ORD)? > With a flight distance of 860 kilometres, it's only a hop from TUP to O'Hare Airport. It might be a quick one, but it's still worth bringing something to read. ### Which airlines fly direct from Tupelo Regional Airport to O'Hare Airport? > Flying nonstop between Tupelo Regional Airport and ORD isn't possible at present. However, you'll still be able to find a flight to Chicago with at least one stop. ### Are Tupelo Regional Airport to O'Hare Intl. Airport (ORD) flight tickets cheaper when they're purchased at the last minute? > Booking last minute from Tupelo Regional Airport to O'Hare Airport can be hit-or-miss. It is possible to find a bargain, but then again, you could miss out entirely! If you'd prefer to start your travel planning early on, Expedia compares flight deals up to 12 months in advance. Just bear in mind that not all airlines release their prices that far in advance. Our advice? Check back often as prices are updated frequently. ## Travel information | Origin airport | Tupelo Regional | | --- | --- | | Destination airport | O'Hare Intl. | | Distance | 855 km | ## Book with confidence ### Compare flights from Tupelo to Chicago easily and book with confidence For travelling on business or for pleasure, Expedia makes it easy to book your flights from Tupelo to Chicago. Operating between them flights per day, airlines cover the route. And fly direct, getting you to O'Hare Intl. in just hours. If you have a preferred carrier, use our advanced search tool to find the right flight from Tupelo Regional to O'Hare Intl..   To make things even better, in the advanced search, you can also choose to fly economy, premium economy, business or first class, select your maximum number of stops, and pick your preferred departure and arrival time. You can also opt for refundable and direct flights.  Grab a great deal on your flight from Tupelo Regional (TUP) to O'Hare Intl. (ORD) The easiest way to view the best deals on flights from Tupelo to Chicago today is to enter your travel dates and hit search. From here, you can sort your results by price to see the cheapest flights first. Right now, return flights from Tupelo Regional to O'Hare Intl. start at just and range up to .   To find an even better deal, try   - being flexible on your dates – midweek flights can be cheaper - looking for other airports near Tupelo and Chicago - booking your flight during , the cheapest month on this route - varying your flight times – early morning and late at night are sometimes cheaper  Why you should book your Tupelo to Chicago flight with Expedia! We cater for all flight types, cabin classes and airlines. So whether you’re booking flights from Tupelo Regional to O'Hare Intl. for a budget break or a business trip with a bit of pleasure thrown in, we make it easy to secure the seat that’s right for you.   Thanks to our supersized inventory that offers great choice all in one place, you know you’ll get a great deal with Expedia. Especially if you bundle your flight together with your hotel, you will unlock amazing savings. 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