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$169+ Cheap flights from Springfield (SGF) 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 7/16. Fares are subject to change and may not be available on all flights or dates of travel.
SGF — CHI
Jul 21 — Jul 281
Tue 7/21
Tue 7/28
1 adult, Economy
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Cheap flight deals from Springfield to Chicago

Cheapest flights from Springfield to Chicago
Explore the most affordable flight options available from Springfield to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 21, 2026.

This American Airlines deal was found by Cheapflights users on 6/19. 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 7/107:53 pm
SGF
-
ORD
Nonstop1h 52m
American Airlines
Mon 7/138:16 am
ORD
-
SGF
Nonstop1h 47m
American Airlines
Deal found 6/19$248
This American Airlines deal was found by Cheapflights users on 6/20. 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 7/117:53 pm
SGF
-
ORD
Nonstop1h 52m
American Airlines
Tue 7/148:16 am
ORD
-
SGF
Nonstop1h 47m
American Airlines
Deal found 6/20$249
This United Airlines deal was found by Cheapflights users on 6/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/126:25 pm
SGF
-
ORD
Nonstop2h 00m
United Airlines
Sat 10/178:50 am
ORD
-
SGF
Nonstop1h 55m
United Airlines
Deal found 6/17$262
This United Airlines deal was found by Cheapflights users on 6/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/106:34 pm
SGF
-
ORD
Nonstop1h 55m
United Airlines
Sun 7/129:30 pm
ORD
-
SGF
Nonstop1h 57m
United Airlines
Deal found 6/19$263
This American Airlines deal was found by Cheapflights users on 6/20. 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.
Mon 10/125:45 am
SGF
-
ORD
Nonstop1h 45m
American Airlines
Sat 10/178:00 am
ORD
-
SGF
Nonstop1h 41m
American Airlines
Deal found 6/20$264
This American Airlines deal was found by Cheapflights users on 6/20. 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 7/117:53 pm
SGF
-
ORD
Nonstop1h 52m
American Airlines
Mon 7/138:16 am
ORD
-
SGF
Nonstop1h 47m
American Airlines
Deal found 6/20$265
This Delta deal was found by Cheapflights users on 6/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/293:30 pm
SGF
-
MDW
1 stop6h 40m
Delta
Sat 10/316:00 am
MDW
-
SGF
1 stop5h 11m
Delta
Deal found 6/20$269
This Delta deal was found by Cheapflights users on 6/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/293:30 pm
SGF
-
ORD
1 stop4h 50m
Delta
Sat 10/317:10 am
ORD
-
SGF
1 stop7h 40m
Delta
Deal found 6/20$269
This Delta deal was found by Cheapflights users on 6/21. 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.
Thu 11/1211:40 am
SGF
-
MDW
2 stops6h 57m
Delta
Mon 11/169:30 am
MDW
-
SGF
2 stops8h 40m
Delta
Deal found 6/21$279
This Delta deal was found by Cheapflights users on 6/21. 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 7/86:53 pm
SGF
-
ORD
1 stop5h 00m
Delta
Sat 7/111:39 pm
ORD
-
SGF
1 stop7h 33m
Delta
Deal found 6/21$284
This Delta deal was found by Cheapflights users on 6/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/1311:38 am
SGF
-
ORD
2 stops6h 51m
Delta
Mon 8/175:30 am
ORD
-
SGF
1 stop5h 23m
Delta
Deal found 6/18$289
This United Airlines deal was found by Cheapflights users on 6/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/216:37 pm
SGF
-
ORD
Nonstop2h 00m
United Airlines
Sun 8/238:50 am
ORD
-
SGF
Nonstop1h 58m
United Airlines
Deal found 6/17$293

Find flight deals from Springfield to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Springfield (SGF) 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 June 21, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$248
(American Airlines)

One-way from

$169
(American Airlines)

Popular in

October

Cheapest in

February

Average price

$351

Good round-trip deal

$376 or less

Good one-way deal

$335 or less
Provider with most accurate pricing for Springfield-Branson-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Springfield-Branson-Chicago (CHI) flights.
Search Deals
From Springfield-Branson to Chicago (CHI)
Search Deals
One-way flight from Springfield-Branson to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 3% potential increase in price ($10 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 2026
Search Deals
Price to beat on a round-trip flight from Springfield-Branson to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Springfield-Branson to Chicago (CHI).
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Springfield 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 June 21, 2026.
Use the filters below to find and compare flights from Springfield to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

SpringfieldChicago

SGF - ORD

SGFORD

Springfield-Branson

Wed 8/26

11:38 am-6:49 pm

1 stop7h 11m

Chicago O'Hare Intl

Sat 8/29

8:05 am-3:10 pm

1 stop7h 05m

$269

SpringfieldChicago

SGF - ORD

SGFORD

Springfield-Branson

Fri 8/21

3:20 pm-8:55 pm

1 stop5h 35m

Chicago O'Hare Intl

Mon 8/24

5:30 am-10:53 am

1 stop5h 23m

$269

SpringfieldChicago

SGF - ORD

SGFORD

Springfield-Branson

Thu 10/29

6:00 am-4:33 pm

2 stops10h 33m

Chicago O'Hare Intl

Sat 10/31

5:30 am-11:11 am

1 stop5h 41m

$274

SpringfieldChicago

SGF - ORD

SGFORD

Springfield-Branson

Thu 8/13

11:38 am-6:29 pm

2 stops6h 51m

Chicago O'Hare Intl

Mon 8/17

1:41 pm-10:21 pm

2 stops8h 40m

$309

SpringfieldChicago

SGF - MDW

SGFMDW

Springfield-Branson

Thu 8/13

11:38 am-6:33 pm

2 stops6h 55m

Chicago Midway

Mon 8/17

6:05 am-10:53 am

1 stop4h 48m

$319

SpringfieldChicago

SGF - MDW

SGFMDW

Springfield-Branson

Fri 8/21

3:20 pm-10:36 pm

1 stop7h 16m

Chicago Midway

Mon 8/24

1:25 pm-10:21 pm

2 stops8h 56m

$345

SpringfieldChicago

SGF - MDW

SGFMDW

Springfield-Branson

Sat 7/4

6:00 am-5:54 pm

2 stops11h 54m

Chicago Midway

Wed 7/8

11:05 am-6:08 pm

1 stop7h 03m

$352

SpringfieldChicago

SGF - MDW

SGFMDW

Springfield-Branson

Wed 7/1

4:08 pm-10:17 pm

1 stop6h 09m

Chicago Midway

Sat 7/4

10:55 am-3:20 pm

1 stop4h 25m

$369

SpringfieldChicago

SGF - MDW

SGFMDW

Springfield-Branson

Wed 8/26

11:38 am-6:33 pm

2 stops6h 55m

Chicago Midway

Sat 8/29

6:05 am-10:53 am

1 stop4h 48m

$409

SpringfieldChicago

SGF - ORD

SGFORD

Springfield-Branson

Sat 7/11

11:32 am-6:46 pm

1 stop7h 14m

Chicago O'Hare Intl

Tue 7/14

2:07 pm-10:10 pm

2 stops8h 03m

$409

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/21

Showing 1-10 of 38 resultsSorted by cheapest first
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Compare providers for flights from Springfield 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 Springfield to Chicago in June.
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 Springfield-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Springfield-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Springfield-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Springfield-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 Springfield-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 Springfield to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Springfield 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 Springfield to Chicago

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

Currently, August is the cheapest month in which you can book a flight from Springfield to Chicago (average of $166). Flying from Springfield to Chicago in June is currently the most expensive (average of $240). 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 SGF to CHI?

Find hourly flight availability from Springfield 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 June 21, 2026.

It’s optimal to fly from Springfield to Chicago in the morning. By choosing this option you can save up to 29% on the cost of your flight, compared to a flight at noon.

Weekly flight availability from Springfield to Chicago

Explore weekly flight availability from Springfield 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 June 21, 2026.

The most flights from SGF to CHI are scheduled on a Friday (24 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (18 on average).

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

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

To ensure you get the cheapest price possible for a flight from Springfield to Chicago, you should look to book at least 29 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

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

Use this chart to determine the cheapest time to fly round-trip from Springfield to Chicago. Price data was last updated on June 20, 2026.

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

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 June 21, 2026.
Read reviews from past customers who have flown United Airlines and American Airlines from Springfield to Chicago. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
9,868 reviews

Boarding

7.7

Entertainment

7.1

Food

6.6

Overall

7.4

Crew

8.1

Comfort

7.3

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
9,868 reviews
United Airlines
7.4
Good
9,868 reviews

Boarding

7.7

Entertainment

7.1

Food

6.6

Overall

7.4

Crew

8.1

Comfort

7.3

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
11,722 reviews
United Airlines
7.4
Good
9,868 reviews

Boarding

7.7

Entertainment

7.1

Food

6.6

Overall

7.4

Crew

8.1

Comfort

7.3

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 Springfield 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 Springfield to Chicago?

    Most people fly from Springfield-Branson (SGF) if they book a flight from Springfield to Chicago. On average, Springfield-Branson has 22 outbound flights to Chicago per day from 2 airlines. Springfield-Branson is conveniently located just 5.3 mi from Springfield’s city center.

  • How long is the flight from Springfield to Chicago?

    For as low as $269, Delta can have you in Chicago from Springfield in 7h 11m. Springfield and Chicago are separated by a distance of 438 mi.

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

    Flying on American Airlines is currently your cheapest option to Chicago, with prices starting at $189. Another option worth looking into is United Airlines, starting at $194 round trip. You may be able to fly from Springfield to Chicago for 33% less than the average price by searching for these airlines.

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

    No one likes to see their flight delayed. When booking a flight from Springfield to Chicago consider choosing Qatar Airways (79%), American Airlines (79%) or Envoy Air (79%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Springfield to Chicago?

    The cheapest flight price from Springfield to Chicago is $243. On average you can expect to pay $1,072. The most popular route, (Springfield-Branson - Chicago O'Hare Intl), can usually be booked for $249.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Springfield 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 Springfield to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Springfield to Chicago (average of $166). Flying from Springfield to Chicago in June is currently the most expensive (average of $240). 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 Springfield to Chicago

Discover the top 2 airlines that operate flights from Springfield 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 June 21, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$189Average$293FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$194Average$356FlexibilityNo cancel feeOn-time69%

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