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$164+ 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 6/15. Fares are subject to change and may not be available on all flights or dates of travel.
DAY — CHI
Jun 21 — Jun 281
Sun 6/21
Sun 6/28
1 adult, Economy
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Cheapflights Tip: The best prices from Dayton to Chicago are usually found in December or February, booked 83 days in advance, depart on a Friday or Saturday and return on a Saturday

Cheap 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 May 22, 2026.

This United Airlines deal was found by Cheapflights users on 5/20. 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 6/276:15 pm
DAY
-
ORD
Nonstop1h 36m
United Airlines
Mon 6/2911:30 am
ORD
-
DAY
Nonstop1h 17m
United Airlines
Deal found 5/20$239
This American Airlines deal was found by Cheapflights users on 5/20. 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 6/118:17 am
DAY
-
ORD
Nonstop1h 33m
American Airlines
Sun 6/1410:00 pm
ORD
-
DAY
Nonstop1h 18m
American Airlines
Deal found 5/20$240
This American Airlines deal was found by Cheapflights users on 5/20. 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 9/175:54 pm
DAY
-
ORD
1 stop6h 45m
American Airlines
Tue 9/228:00 am
ORD
-
DAY
Nonstop1h 22m
American Airlines
Deal found 5/20$249
This American Airlines deal was found by Cheapflights users on 5/20. 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 9/105:35 pm
DAY
-
ORD
Nonstop1h 25m
American Airlines
Sun 9/138:00 am
ORD
-
DAY
Nonstop1h 22m
American Airlines
Deal found 5/20$254
This American Airlines deal was found by Cheapflights users on 5/20. 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 6/275:57 pm
DAY
-
ORD
1 stop7h 01m
American Airlines
Mon 6/291:19 pm
ORD
-
DAY
1 stop7h 47m
American Airlines
Deal found 5/20$259
This American Airlines deal was found by Cheapflights users on 5/20. 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 8/276:33 pm
DAY
-
ORD
1 stop6h 26m
American Airlines
Sun 8/309:30 am
ORD
-
DAY
Nonstop1h 21m
American Airlines
Deal found 5/20$264
This American Airlines deal was found by Cheapflights users on 5/20. 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 8/205:51 pm
DAY
-
ORD
Nonstop1h 36m
American Airlines
Sun 8/239:30 am
ORD
-
DAY
Nonstop1h 21m
American Airlines
Deal found 5/20$269
This American Airlines deal was found by Cheapflights users on 5/18. 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 7/212:24 pm
DAY
-
ORD
Nonstop1h 25m
American Airlines
Thu 7/98:00 am
ORD
-
DAY
1 stop4h 44m
American Airlines
Deal found 5/18$278
This American Airlines deal was found by Cheapflights users on 5/19. 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 6/52:02 pm
DAY
-
ORD
1 stop6h 43m
American Airlines
Sun 6/710:00 pm
ORD
-
DAY
Nonstop1h 18m
American Airlines
Deal found 5/19$279
This American Airlines deal was found by Cheapflights users on 5/22. 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 5/2912:03 pm
DAY
-
ORD
Nonstop1h 31m
American Airlines
Fri 6/510:00 pm
ORD
-
DAY
Nonstop1h 18m
American Airlines
Deal found 5/22$284
This American Airlines deal was found by Cheapflights users on 5/20. 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.
Wed 6/175:57 pm
DAY
-
ORD
1 stop7h 01m
American Airlines
Wed 6/245:10 am
ORD
-
DAY
1 stop7h 21m
American Airlines
Deal found 5/20$289
This Delta deal was found by Cheapflights users on 5/17. 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.
Tue 8/256:00 am
DAY
-
MDW
2 stops13h 01m
Delta
Tue 9/16:45 pm
MDW
-
DAY
2 stops18h 14m
Delta
Deal found 5/17$381

Find 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 May 22, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$239
(United Airlines)

One-way from

$164
(American Airlines)

Popular in

March

Cheapest in

December

Average price

$269

Good round-trip deal

$368 or less

Good one-way deal

$276 or less
Provider with most accurate pricing for Dayton-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Dayton-Chicago (CHI) flights.
Search Deals
From Dayton to Chicago (CHI)
Search Deals
One-way flight from Dayton to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 1% potential increase in price ($2 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
Search Deals
Price to beat on a round-trip flight from Dayton to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Dayton to Chicago (CHI).
Search Deals

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 May 22, 2026.
Use the filters below to find and compare flights from Dayton to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

DaytonChicago

DAY - ORD

DAYORD

Dayton

Sat 6/27

6:15 pm-6:51 pm

Nonstop1h 36m

Chicago O'Hare Intl

Mon 6/29

11:30 am-1:47 pm

Nonstop1h 17m

$239

DaytonChicago

DAY - ORD

DAYORD

Dayton

Sun 8/2

6:00 am-6:15 am

Nonstop1h 15m

Chicago O'Hare Intl

Sat 8/8

3:00 pm-5:30 pm

Nonstop1h 30m

$249

DaytonChicago

DAY - ORD

DAYORD

Dayton

Mon 6/1

6:10 pm-6:46 pm

Nonstop1h 36m

Chicago O'Hare Intl

Fri 7/10

8:40 am-11:04 am

Nonstop1h 24m

$269

DaytonChicago

DAY - ORD

DAYORD

Dayton

Thu 8/27

7:15 am-7:53 am

Nonstop1h 38m

Chicago O'Hare Intl

Wed 9/2

8:33 am-10:55 am

Nonstop1h 22m

$309
Quickest round-trip

DaytonChicago

DAY - ORD

DAYORD

Dayton

Wed 6/24

11:39 am-12:05 pm

Nonstop1h 26m

Chicago O'Hare Intl

Mon 6/29

11:30 am-1:47 pm

Nonstop1h 17m

$309

DaytonChicago

DAY - ORD

DAYORD

Dayton

Thu 7/2

2:23 pm-2:55 pm

Nonstop1h 32m

Chicago O'Hare Intl

Sun 7/5

8:40 am-11:04 am

Nonstop1h 24m

$324

DaytonChicago

DAY - ORD

DAYORD

Dayton

Sat 7/11

6:31 am-12:19 pm

1 stop6h 48m

Chicago O'Hare Intl

Mon 7/13

1:32 pm-9:25 pm

1 stop6h 53m

$358

DaytonChicago

DAY - ORD

DAYORD

Dayton

Sat 9/5

6:00 pm-6:33 pm

Nonstop1h 33m

Chicago O'Hare Intl

Mon 9/7

6:25 am-2:15 pm

1 stop6h 50m

$383

DaytonChicago

DAY - ORD

DAYORD

Dayton

Sat 9/5

2:50 pm-6:37 pm

1 stop4h 47m

Chicago O'Hare Intl

Wed 9/9

4:00 pm-6:29 pm

Nonstop1h 29m

$383

DaytonChicago

DAY - ORD

DAYORD

Dayton

Mon 8/24

7:15 am-7:53 am

Nonstop1h 38m

Chicago O'Hare Intl

Thu 8/27

8:33 am-10:55 am

Nonstop1h 22m

$397

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/18

Showing 1-10 of 52 resultsSorted by cheapest first
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2
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6

Compare providers for flights from Dayton to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Dayton to Chicago in May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Dayton-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Dayton-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Dayton-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Dayton-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Dayton-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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

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

Currently, July is the cheapest month in which you can book a flight from Dayton to Chicago (average of $134). Flying from Dayton to Chicago in May is currently the most expensive (average of $194). 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 May 22, 2026.

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 40% on airfare.

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 May 22, 2026.

The most flights from DAY to CHI are scheduled on a Friday (32 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (15 on average).

How much does it cost to fly round-trip from Dayton to Chicago?

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

The best time to book flights from Dayton to Chicago is 58 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 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 May 16, 2026.

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

The best insider tips for Dayton to Chicago flights

AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Dayton to Chicago trip
Our travel experts
Brandon Schultz

Brandon Schultz

Expert on Qatar Airways

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 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

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 May 22, 2026.
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
9,751 reviews

Entertainment

7.1

Crew

8.1

Comfort

7.3

Food

6.6

Overall

7.4

Boarding

7.7

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
United Airlines
7.4
Good
9,751 reviews
United Airlines
7.4
Good
9,751 reviews

Entertainment

7.1

Crew

8.1

Comfort

7.3

Food

6.6

Overall

7.4

Boarding

7.7

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
American Airlines
7.1
Good
11,644 reviews
United Airlines
7.4
Good
9,751 reviews

Entertainment

7.1

Crew

8.1

Comfort

7.3

Food

6.6

Overall

7.4

Boarding

7.7

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.

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 27 outbound flights to Chicago per day from 2 airlines. Dayton is conveniently located just 10.0 mi from Dayton’s city center.

  • How long is the flight from Dayton to Chicago?

    Departing from Dayton to Chicago will take you 1h 36m. There are 240 mi between Dayton and Chicago. This flight may include one or multiple stops.

  • 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 $179 round trip. You may be able to fly from Dayton to Chicago for 30% 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: Republic Airways (89%), Envoy Air (85%), Japan Airlines( 84%).

  • What are the cheapest flights from Dayton to Chicago?

    Looking for the cheapest flight from Dayton to Chicago? While on average our users pay $1,055, our data indicates the cheapest price to be $218. The most popular route (Dayton - Chicago O'Hare Intl), is priced around $239.

  • 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, July is the cheapest month in which you can book a flight from Dayton to Chicago (average of $134). Flying from Dayton to Chicago in May is currently the most expensive (average of $194). 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
Benton Harbor
Lansing
Merrillville
Hammond
Porter

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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 May 22, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$179Average$305FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$179Average$282FlexibilityNo cancel feeOn-time71%

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