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$269 Cheap Flights from Tri-Cities (TRI) to Chicago (MDW)

View $269 flight on Sat, Oct 31, 2026Opens in a new window

Popular airlines from Tri-Cities, TN (TRI-Tri-Cities Regional) to Chicago Midway Airport (MDW)

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Cheap Flights from Tri-Cities to Chicago (TRI-MDW)

Prices were available within the past 7 days and start at $269 for one-way flights and $299 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Sat, Oct 31 - Sun, Nov 1
TRI
Tri-Cities
MDW
Chicago
$299 Roundtrip, just found
$299
Roundtrip
just found
Select Delta flight, departing Sat, Oct 31 from Tri-Cities to Chicago, returning Sun, Nov 1, priced at $299 just found
Delta
Wed, Sep 23 - Wed, Sep 30
TRI
Tri-Cities
MDW
Chicago
$314 Roundtrip, found 1 day ago
$314
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Sep 23 from Tri-Cities to Chicago, returning Wed, Sep 30, priced at $314 found 1 day ago
Delta
Tue, Nov 3 - Sat, Nov 7
TRI
Tri-Cities
MDW
Chicago
$317 Roundtrip, found 2 hours ago
$317
Roundtrip
found 2 hours ago
Select Delta flight, departing Tue, Nov 3 from Tri-Cities to Chicago, returning Sat, Nov 7, priced at $317 found 2 hours ago
Delta
Sat, Sep 19 - Sat, Sep 26
TRI
Tri-Cities
MDW
Chicago
$334 Roundtrip, found 5 days ago
$334
Roundtrip
found 5 days ago
Select Delta flight, departing Sat, Sep 19 from Tri-Cities to Chicago, returning Sat, Sep 26, priced at $334 found 5 days ago
Delta
Wed, Jan 6 - Sat, Jan 9
TRI
Tri-Cities
MDW
Chicago
$337 Roundtrip, found 3 days ago
$337
Roundtrip
found 3 days ago
Select Delta flight, departing Wed, Jan 6 from Tri-Cities to Chicago, returning Sat, Jan 9, priced at $337 found 3 days ago
Delta
Thu, Nov 26 - Sun, Nov 29
TRI
Tri-Cities
MDW
Chicago
$339 Roundtrip, found 2 days ago
$339
Roundtrip
found 2 days ago
Select Delta flight, departing Thu, Nov 26 from Tri-Cities to Chicago, returning Sun, Nov 29, priced at $339 found 2 days ago
Delta
Thu, May 27 - Sun, May 30
TRI
Tri-Cities
MDW
Chicago
$355 Roundtrip, found 1 hour ago
$355
Roundtrip
found 1 hour ago
Select Delta flight, departing Thu, May 27 from Tri-Cities to Chicago, returning Sun, May 30, priced at $355 found 1 hour ago
Delta
Wed, Sep 23 - Sat, Sep 26
TRI
Tri-Cities
MDW
Chicago
$359 Roundtrip, found 7 hours ago
$359
Roundtrip
found 7 hours ago
Select Delta flight, departing Wed, Sep 23 from Tri-Cities to Chicago, returning Sat, Sep 26, priced at $359 found 7 hours ago
Delta
Sat, Oct 31 - Sun, Nov 1
TRI
Tri-Cities
MDW
Chicago
$362 Roundtrip, just found
$362
Roundtrip
just found
Select Delta flight, departing Sat, Oct 31 from Tri-Cities to Chicago, returning Sun, Nov 1, priced at $362 just found
Delta
Fri, Sep 25 - Mon, Sep 28
TRI
Tri-Cities
MDW
Chicago
$364 Roundtrip, found 22 hours ago
$364
Roundtrip
found 22 hours ago
Select Delta flight, departing Fri, Sep 25 from Tri-Cities to Chicago, returning Mon, Sep 28, priced at $364 found 22 hours 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 $309
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $309

What you need to know for your flight from Tri-Cities Regional to Midway Intl.

Tri-Cities (TRI) to Chicago (MDW) at a glance

Travel with a full-service airline from Tri-Cities (TRI) to Chicago (MDW) on this domestic short-haul route. Discover the flight options that align with your schedule and travel plans as you explore Chicago's renowned attractions and neighborhoods. Here are the essential details for flights from Tri-Cities Regional Airport (TRI) to Midway International Airport (MDW).

  • Fastest flight duration: around 3h 15m in-flight, plus roughly 1h 30m layover with one stop
  • Route distance: roughly 450 miles (725 km)
  • Flights per week: around 7 departures on average
  • Typical fares (one-way): economy tickets often range from $110–$475, depending on seasonality and how far ahead you book

Flights from Tri-Cities Regional Airport (TRI) to Midway International Airport (MDW)

Based on the latest traveler bookings, here are the most popular airlines for flights from Tri-Cities to Chicago, typically favored for their one-stop services. Many routes include a layover at Hartsfield-Jackson Atlanta International Airport (ATL), with a typical duration of around 1 hour and 30 minutes. This allows you the flexibility to compare prices, total travel times, and cabin classes to find the ideal itinerary.

  • Delta: As a comprehensive airline, Delta provides convenient one-stop flights, with one-way ticket prices generally falling between $110 and $475. This carrier dominates the route, offering a flying duration of 3 hours and 15 minutes, leading to a total travel time of approximately 4 hours and 45 minutes, including layover time.

Alternative route from Tri-Cities (TRI) to Chicago (MDW)

  • Tri-Cities to Chicago (TRI-ORD): O'Hare International Airport (ORD) is located approximately 16 miles from Midway International Airport (MDW). One-way economy ticket prices on this route generally vary between $115 and $410, influenced by the season and how early you book. The journey often includes one-stop options, with frequent layovers at Charlotte-Douglas International Airport (CLT) and Hartsfield-Jackson Atlanta International Airport (ATL). Major airlines servicing this route include American Airlines and Delta. Additionally, first-class service is offered for travelers seeking a more premium experience.

How to find the best prices for flights from Tri-Cities (TRI) to Chicago (MDW)

Getting some of the best deals on flights from Tri-Cities to Chicago is all about timing and flexibility. Here are some key tips to help you save:

  1. Best times to book and fly: cheaper fares are usually found when booking 2 to 8 weeks in advance, although most travelers tend to book within 2 weeks. Morning departures between 5 AM and 12 PM often offer lower prices and are the most popular flight times, while flying on Thursday not only provides cheaper rates but is also the most favored travel day.
  2. Set up price alerts: stay updated on price changes by using Expedia's Price Tracker. Receive alerts when fares drop for your selected route.
  3. Bundle and save: bundle your flight and hotel to save on Expedia, or unlock a hotel deal after booking your flight.*
  4. Compare flight options: use Expedia's search tool to compare airlines, routes, direct vs. non-direct flights, and flight times. You can also sort by price to find the most affordable options.
  5. Stay flexible with dates: being open to different travel days can sometimes help you find better prices on flights and hotels.
  6. Think about luggage: nowadays, it's important to check the airline's baggage policies to find the best value. That may be paying for an additional carry-on bag or booking a ticket with checked luggage included. Either way, double-check your allowance before confirming your booking to avoid excess baggage fees at the airport.

*Members only. Savings vary and are not available on all bundles. Select hotels.

Arriving at Midway International Airport from Tri-Cities Regional Airport

Chicago welcomes travelers from Tri-Cities with a range of transport options based on price, convenience, and proximity. Here's how to reach Chicago efficiently:

  • Hotel transfer: Transfers offer a convenient way to reach your hotel in Chicago, with private rides that can be arranged in advance.
  • Car rental: Renting a car from Midway International Airport is a great option if you plan to explore and sightsee beyond the city. Browse cheap car rentals at Midway International Airport on Expedia.
  • Taxi/ride-hailing: Taxis and ride-hailing services may be available from designated pickup areas outside the terminal, check locally on arrival.
  • Public transportation: From Midway International Airport, travelers will find several key transport links nearby. Midway Station, a metro station, is located about 0.2 miles away on foot, while Chicago Ashburn Station, a train station, is about 4.1 miles from the airport and can be reached by car. Additionally, Lyons Seaport, a seaport, is situated approximately 7.2 miles away by car.

Frequently asked questions

How much does a flight from Tri-Cities, TN (TRI-Tri-Cities Regional) to Chicago, IL (MDW-Midway Intl.) cost?
You can find cheap one-way flights from $269 and cheap return flights from $299 Tri-Cities, TN (TRI-Tri-Cities Regional) to Chicago, IL (MDW-Midway Intl.) with Expedia. One-way flights generally range between $218 and $338, and roundtrip flights usually range from $346 to $1132. Flight prices vary based on the month and day of the week you want to travel, as well as the airline and how far in advance you book your ticket. Filter your search on Expedia by "Price (lowest to highest)" to see the cheapest fares first, and use the Price Tracking tool to receive alerts when Tri-Cities, TN (TRI-Tri-Cities Regional) to Chicago, IL (MDW-Midway Intl.) ticket fares go up or down.*Typical price ranges based on flights available on Expedia in the last year. Prices include multi-airline options.
What is the cheapest month to fly from Tri-Cities, TN (TRI-Tri-Cities Regional) to Chicago, IL (MDW-Midway Intl.)?
The cheapest month to fly from TRI to MDW is October when demand is low. Traveling in off-peak or shoulder months is usually a good way to secure cheap tickets, just remember to avoid flying during holidays if you're able to. Use the calendar view in your search to see which months have low fares on this route.
Which airlines fly direct from Tri-Cities, TN (TRI-Tri-Cities Regional) to Chicago, IL (MDW-Midway Intl.)?
Enter TRI to MDW and your travel dates, then apply the 'Nonstop' filter to see only direct flights.
What is the cheapest airline that flies from Tri-Cities, TN (TRI-Tri-Cities Regional) to Chicago, IL (MDW-Midway Intl.)?
Delta is one of the cheapest airlines offering connecting flights from Tri-Cities, TN (TRI) to Chicago, IL (MDW), with round-trip tickets starting from around $346.37. Use Expedia's search tool to compare the prices and schedules of airlines that fly this route to find the best option for your plans and budget.*Prices based on flights available on Expedia in the last year.
How do I find cheap flights from Tri-Cities, TN (TRI-Tri-Cities Regional) to Chicago, IL (MDW-Midway Intl.)?
To find a cheap flight from Tri-Cities, TN (TRI-Tri-Cities Regional) to Chicago, IL (MDW-Midway Intl.), be flexible with your dates. Traveling outside of peak vacation months and booking a mid-week flight can help you save. Early morning and late night flights are often more affordable, too. Expedia allows you to compare flight times, airlines and routes all in one place to find low fares. You can also set up Price Tracking and receive alerts when fares go up or down.
What is the best time to fly from Tri-Cities, TN (TRI-Tri-Cities Regional) to Chicago, IL (MDW-Midway Intl.)?
The best time to fly is usually mid-week (Tuesday or Wednesday) and during early morning hours as flights tend to be cheaper, less crowded, and generally more on-time. Avoid major holidays and peak vacation seasons for smoother travel. Combining off-peak days and hours often gives the best combination of cost, comfort, and convenience.
What is the earliest flight from Tri-Cities, TN (TRI-Tri-Cities Regional) to Chicago, IL (MDW-Midway Intl.)?
The earliest flight from Tri-Cities, TN (TRI) to Chicago, IL (MDW) usually departs at around 6:00 AM, operated by Delta. This seasonal service is available in June and July, giving you a great opportunity to maximize your time in Chicago. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.
What are the most popular departure times for flights from Tri-Cities, TN (TRI-Tri-Cities Regional) to Chicago, IL (MDW-Midway Intl.)?
The most popular departure times for flights from Tri-Cities Regional (TRI) to Midway Intl. (MDW) are in the early morning, from 6am to 9am. About 33% of passengers prefer this time window. Delta Air Lines is a major carrier offering flights during this window. This timing is convenient for travelers looking to start their day in Chicago.
How long does it take to fly from Tri-Cities, TN (TRI-Tri-Cities Regional) to Chicago, IL (MDW-Midway Intl.)?
Flying from TRI to MDW with a connection usually takes about 4 hours 50 minutes, traveling roughly 465 miles. Keep in mind that actual flight times can vary due to wind patterns, weather, and air traffic.
Can you fly business or first class from Tri-Cities, TN (TRI-Tri-Cities Regional) to Chicago, IL (MDW-Midway Intl.)?
First class seats are offered on the TRI to MDW route with Delta Air Lines.
How do I earn miles on a Tri-Cities, TN (TRI-Tri-Cities Regional) to Chicago, IL (MDW-Midway Intl.) flight with Expedia?
It's easy to earn miles on a Tri-Cities, TN (TRI-Tri-Cities Regional) to Chicago, IL (MDW-Midway Intl.) flight when you book with Expedia. Before you confirm your booking, simply select your frequent flyer program and enter your program number. As a member of One Key™, you can also earn OneKeyCash™* on top of your airline miles when you book with Expedia.*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
What airports do you fly into for Chicago from Tri-Cities Regional (TRI)?
When traveling from Tri-Cities Regional (TRI) to Chicago, you can fly into Midway Intl. (MDW) and O'Hare Intl. (ORD). Some flights may connect through major hubs like Hartsfield-Jackson Atlanta Intl. (ATL) before reaching Chicago. Compare routes and airports on Expedia to find the best flight options for your travel plans.
Is it cheaper to buy a plane ticket from Tri-Cities, TN (TRI-Tri-Cities Regional) to Chicago, IL (MDW-Midway Intl.) at the last minute?
Typically, booking a last minute flight from Tri-Cities, TN (TRI-Tri-Cities Regional) to Chicago, IL (MDW-Midway Intl.) will be more expensive than booking in advance. As the departure date approaches, there are usually fewer seats available which can drive up the cost. However, if there's some wiggle room with your travel dates and times, you could bag a cheap last-minute fare.
Is it cheaper to book a Tri-Cities, TN (TRI-Tri-Cities Regional) to Chicago, IL (MDW-Midway Intl.) flight and hotel package?
Securing a Tri-Cities, TN (TRI-Tri-Cities Regional) to Chicago, IL (MDW-Midway Intl.) Chicago Vacation Packages is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our extensive range of stays and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Tri-Cities, TN (TRI-Tri-Cities Regional) to Chicago, IL (MDW-Midway Intl.)?
If you booked your Tri-Cities, TN (TRI-Tri-Cities Regional) to Chicago, IL (MDW-Midway Intl.) flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you'd like more information.

Travel information

Origin airport
Tri-Cities Regional
Destination airport
Midway Intl.
Airlines serving
Delta
Roundtrip price
$298
Distance
464 mi

Book with confidence

Tri-Cities to Chicago Flights

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

 

The best time to book a flight from Tri-Cities to Chicago

Sunday is one of the best days to book for cheap flights from Tri-Cities 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 Tri-Cities 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 Tri-Cities to Chicago in 2026. You can also book with separate airlines for your outbound and return journeys, from $269 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 Tri-Cities 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 Tri-Cities 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.

 

Tri-Cities to Chicago Flights

*Flight schedules are subject to change.

*Available to One Key members.

 

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