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$128+ Cheap flights from Dayton (DAY) to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/16. Fares are subject to change and may not be available on all flights or dates of travel.
DAY — CHI
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
1 adult, Economy
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Cheapflights Tip: The best prices from Dayton to Chicago are usually found in January or August, booked 79 days in advance, depart on a Thursday or Saturday and return on a Saturday

Cheap flight deals from Dayton to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Dayton (DAY) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated August 14, 2025.

Round-trip from

$179
(United Airlines)

One-way from

$130
(Kiwi.com)

Popular in

June

Cheapest in

January

Average price

$249

Good round-trip deal

$341 or less

Good one-way deal

$260 or less
From Dayton to Chicago (CHI)
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One-way flight from Dayton to Chicago (CHI)
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Highest demand for flights based on searches. 11% potential increase in price ($36 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Price to beat on a round-trip flight from Dayton to Chicago (CHI).
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Price to beat on a one-way flight from Dayton to Chicago (CHI).
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Find flight deals from Dayton to Chicago

Cheapest flights from Dayton to Chicago
Explore the most affordable flight options available from Dayton to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 14, 2025.

This American Airlines deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1912:42 pmDAY - ORD
Nonstop1h 26mAmerican Airlines
Thu 10/29:03 amORD - DAY
Nonstop1h 25mAmerican Airlines
Deal found 8/14$179
This American Airlines deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/410:30 amDAY - ORD
Nonstop1h 32mAmerican Airlines
Sun 9/78:26 pmORD - DAY
Nonstop1h 29mAmerican Airlines
Deal found 8/12$180
This United Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/309:00 amDAY - ORD
Nonstop1h 29mUnited Airlines
Mon 9/18:45 amORD - DAY
Nonstop1h 22mUnited Airlines
Deal found 8/11$184
This American Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/2612:43 pmDAY - ORD
Nonstop1h 26mAmerican Airlines
Sat 8/302:34 pmORD - DAY
Nonstop1h 16mAmerican Airlines
Deal found 8/11$189
This United Airlines deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/249:00 amDAY - ORD
Nonstop1h 30mUnited Airlines
Sat 8/305:50 pmORD - DAY
Nonstop1h 22mUnited Airlines
Deal found 8/12$199
This American Airlines deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/1912:43 pmDAY - ORD
Nonstop1h 26mAmerican Airlines
Sun 8/247:30 pmORD - DAY
Nonstop1h 18mAmerican Airlines
Deal found 8/12$209
This United Airlines deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2811:42 amDAY - ORD
Nonstop1h 28mUnited Airlines
Sat 8/302:25 pmORD - DAY
Nonstop1h 23mUnited Airlines
Deal found 8/13$219
This American Airlines deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/135:18 pmDAY - ORD
Nonstop1h 32mAmerican Airlines
Mon 10/207:10 amORD - DAY
1 stop5h 15mAmerican Airlines
Deal found 8/14$223
This American Airlines deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/178:25 amDAY - ORD
Nonstop1h 26mAmerican Airlines
Sun 10/199:32 amORD - DAY
Nonstop1h 23mAmerican Airlines
Deal found 8/12$224
This American Airlines deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/227:27 pmDAY - ORD
1 stop12h 49mAmerican Airlines
Sun 11/239:50 amORD - DAY
Nonstop1h 19mAmerican Airlines
Deal found 8/14$229
This American Airlines deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/198:17 amDAY - ORD
Nonstop1h 26mAmerican Airlines
Mon 9/225:00 amORD - DAY
1 stop6h 26mAmerican Airlines
Deal found 8/13$234
This Delta deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/1711:05 amDAY - MDW
1 stop11h 39mDelta
Thu 12/256:00 amMDW - DAY
1 stop14h 04mDelta
Deal found 8/13$348

Cheapflights Fare Finder

 
Customize your flight search to find flights from Dayton to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 14, 2025.
Use the filters below to find and compare flights from Dayton to Chicago that are best for you.

Fly from

Dayton

Fly to

Chicago

Route

Depart

Return

Price

DaytonChicago

DAY - ORD

DAYORD

Dayton

Sat 10/11

5:55 pm-6:24 pm

Nonstop1h 29m

Chicago O'Hare Intl

Sun 10/12

5:50 pm-8:09 pm

Nonstop1h 19m

$179

DaytonChicago

DAY - ORD

DAYORD

Dayton

Thu 9/11

8:17 am-8:43 am

Nonstop1h 26m

Chicago O'Hare Intl

Thu 9/18

9:03 am-11:28 am

Nonstop1h 25m

$179

DaytonChicago

DAY - ORD

DAYORD

Dayton

Fri 10/10

7:21 am-7:51 am

Nonstop1h 30m

Chicago O'Hare Intl

Sun 10/12

9:18 pm-11:44 pm

Nonstop1h 26m

$179

DaytonChicago

DAY - ORD

DAYORD

Dayton

Sat 11/22

8:38 am-9:10 am

Nonstop1h 32m

Chicago O'Hare Intl

Sun 11/23

9:35 pm-11:55 pm

Nonstop1h 20m

$179

DaytonChicago

DAY - ORD

DAYORD

Dayton

Fri 10/17

9:00 am-9:26 am

Nonstop1h 26m

Chicago O'Hare Intl

Sat 10/18

8:45 am-11:07 am

Nonstop1h 22m

$179

DaytonChicago

DAY - ORD

DAYORD

Dayton

Thu 9/25

8:17 am-8:43 am

Nonstop1h 26m

Chicago O'Hare Intl

Sun 9/28

9:03 am-11:28 am

Nonstop1h 25m

$179

DaytonChicago

DAY - ORD

DAYORD

Dayton

Wed 9/17

6:52 am-7:23 am

Nonstop1h 31m

Chicago O'Hare Intl

Wed 9/24

9:03 am-11:28 am

Nonstop1h 25m

$179

DaytonChicago

DAY - ORD

DAYORD

Dayton

Wed 10/29

5:18 pm-5:50 pm

Nonstop1h 32m

Chicago O'Hare Intl

Tue 11/4

9:35 pm-11:55 pm

Nonstop1h 20m

$179

DaytonChicago

DAY - ORD

DAYORD

Dayton

Tue 9/30

5:01 pm-5:29 pm

Nonstop1h 28m

Chicago O'Hare Intl

Sun 10/5

9:03 am-11:28 am

Nonstop1h 25m

$179

DaytonChicago

DAY - ORD

DAYORD

Dayton

Fri 9/5

5:01 pm-5:29 pm

Nonstop1h 28m

Chicago O'Hare Intl

Sun 9/7

8:26 pm-10:55 pm

Nonstop1h 29m

$179

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/12

Showing 1-10 of 39 results
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The best insider tips for Dayton to Chicago flights

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
Cheapflights partnered with top experts to bring you the best recommendations for your Dayton to Chicago trip
Airlines
Qatar Airways

Qatar Airways allows only one carry-on item in economy; plan ahead to avoid extra fees.


Qatar Airways offers extra legroom seats for a fee; ideal for those needing more space.

Read more about Qatar Airwaysby Brandon Schultz
United Airlines

United's Economy Plus offers extra legroom; ideal for a more comfortable short flight.


United Airlines' Basic Economy restricts carry-ons; only a personal item allowed.

Read more about United Airlinesby Harriet Baskas
Our travel experts
Brandon Schultz

Brandon Schultz

Expert on Qatar Airways

Brandon Schultz

Brandon Schultz

Brandon Schultz is an award-winning food and travel writer based in New York City. His work has appeared in Forbes, AAA, Thrillist, Travel + Leisure, and The Daily Meal, among many others, and he is the author of 6 books, including 3 cookbooks.

Read more
Harriet Baskas

Harriet Baskas

Expert on United Airlines

Harriet Baskas

Harriet Baskas

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Read more

Best time to book a flight from Dayton to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Dayton with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Dayton to Chicago

How far ahead should I book a flight from Dayton to Chicago?

Use this chart to determine the optimal time to book a round-trip flight from Dayton to Chicago. Price data was last updated on August 8, 2025.

The best time to book flights from Dayton to Chicago is 79 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

What is the cheapest month to book a flight from Dayton to Chicago?

Currently, August is the cheapest month in which you can book a flight from Dayton to Chicago (average of $245). Flying from Dayton to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from DAY to CHI?

Find hourly flight availability from Dayton to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 14, 2025.

One of the essential ways to save on airfare from Dayton to Chicago is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the morning could potentially save you up to 18% on airfare.

What is the cheapest day to fly from Dayton to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Dayton to Chicago. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Dayton to Chicago flight should consider departing on Friday evenings when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Dayton to Chicago

Explore weekly flight availability from Dayton to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated August 14, 2025.

The most flights from DAY to CHI are scheduled on a Thursday (30 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (14 on average).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated August 14, 2025.
Get a feel of what it's like to fly with United Airlines and American Airlines from Dayton to Chicago by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
8,916 reviews

Overall

7.4

Entertainment

7.1

Crew

8.1

Comfort

7.3

Boarding

7.7

Food

6.6

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
United Airlines
7.4
Good
8,916 reviews
United Airlines
7.4
Good
8,916 reviews

Overall

7.4

Entertainment

7.1

Crew

8.1

Comfort

7.3

Boarding

7.7

Food

6.6

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
American Airlines
7.2
Good
10,000 reviews
United Airlines
7.4
Good
8,916 reviews

Overall

7.4

Entertainment

7.1

Crew

8.1

Comfort

7.3

Boarding

7.7

Food

6.6

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!

Related info for your journey

Find useful and relevant information for your journey from Dayton to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Dayton to Chicago?

    Most people fly from Dayton (DAY) if they book a flight from Dayton to Chicago. On average, Dayton has 25 outbound flights to Chicago per day from 2 airlines. Dayton is conveniently located just 10.0 mi from Dayton’s city center.

  • What are the cheapest airlines flying from Dayton to Chicago round-trip?

    Flying on American Airlines is currently your cheapest option to Chicago, with prices starting at $179. Another option worth looking into is United Airlines, starting at $193 round trip. You may be able to fly from Dayton to Chicago for 38% less than the average price by searching for these airlines.

  • What are the most popular routes from Dayton to Chicago?

    When deciding which route to take from Dayton to Chicago consider Dayton - Chicago O'Hare Intl, Dayton - Chicago Midway or Dayton - Chicago Greater Rockford as they are the most popular.

  • What are the most reliable airlines from Dayton to Chicago?

    Before booking your flight to Chicago from Dayton, check out the most reliable airlines to get you to your destination on time: SkyWest Airlines (85%), ANA (84%), United Airlines( 80%).

  • What are the cheapest flights from Dayton to Chicago?

    Looking for the cheapest flight from Dayton to Chicago? While on average our users pay $825, our data indicates the cheapest price to be $196. The most popular route (Dayton - Chicago O'Hare Intl), is priced around $179.

  • Can I find deals for flights from Dayton to Chicago that include hotel bookings?

    Yes. In addition to deals on Dayton to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Dayton to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Dayton to Chicago.

  • Can I find deals for business class flights from Dayton to Chicago?

    Yes. Cheapflights offers flight deals from Dayton to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Dayton to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Dayton to Chicago (average of $245). Flying from Dayton to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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Top 2 airlines flying from Dayton to Chicago

Discover the top 2 airlines that operate flights from Dayton to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$179Average$293FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$193Average$305FlexibilityNo cancel feeOn-time69%

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