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$79+ Cheap flights from Chicago (CHI) to Springfield, MA, MA

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 10/21. Fares are subject to change and may not be available on all flights or dates of travel.
CHI
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Springfield are usually found in August or September, booked 64 days in advance, depart on a Saturday or Wednesday and return on a Thursday

Cheap flight deals from Chicago to Springfield

Keep the following information in mind while searching for Chicago to Springfield flight deals. Data was last updated September 15, 2025.

Round-trip from

$182
(Southwest)

One-way from

$79
(United Airlines)

Popular in

December

Cheapest in

August

Average price

$323
From Chicago (CHI) to Springfield
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One-way flight from Chicago (CHI) to Springfield
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Highest demand for flights based on searches. 10% potential increase in price ($42 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Chicago to Springfield

Cheapest flights from Chicago to Springfield
Explore the most affordable flight options available from Chicago to Springfield. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 15, 2025.

This Southwest deal was found by Cheapflights users on 9/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/69:05 pmMDW - BDL
1 stop10h 00mSouthwest
Sun 11/93:35 pmBDL - MDW
1 stop8h 35mSouthwest
Deal found 9/14$182
This United Airlines deal was found by Cheapflights users on 9/12. 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.
Wed 10/14:00 pmORD - BDL
1 stop6h 57mUnited Airlines
Fri 10/37:53 pmBDL - ORD
1 stop4h 22mUnited Airlines
Deal found 9/12$185
This Frontier deal was found by Cheapflights users on 9/13. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/199:48 amMDW - BDL
1 stop9h 09mFrontier
Sun 9/218:37 pmBDL - MDW
1 stop11h 46mFrontier
Deal found 9/13$188
This Delta deal was found by Cheapflights users on 9/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/307:20 amORD - BDL
1 stop5h 11mDelta
Tue 10/75:30 amBDL - ORD
1 stop5h 13mDelta
Deal found 9/12$197
This Delta deal was found by Cheapflights users on 9/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/3012:43 pmMDW - BDL
1 stop6h 44mDelta
Tue 10/75:30 amBDL - MDW
1 stop4h 10mDelta
Deal found 9/12$197
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/205:05 amORD - BDL
1 stop9h 16mMultiple Airlines
Fri 10/317:10 pmBDL - ORD
1 stop16h 40mMultiple Airlines
Deal found 9/13$201
This United Airlines deal was found by Cheapflights users on 9/13. 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 11/611:01 amORD - BDL
Nonstop2h 10mUnited Airlines
Sun 11/96:10 amBDL - ORD
Nonstop2h 52mUnited Airlines
Deal found 9/13$202
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/309:43 pmMDW - BDL
2 stops35h 19mMultiple Airlines
Thu 11/610:42 amBDL - MDW
1 stop8h 57mMultiple Airlines
Deal found 9/15$204
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/66:18 pmORD - BDL
2 stops16h 55mMultiple Airlines
Sat 10/115:07 pmBDL - ORD
1 stop18h 43mMultiple Airlines
Deal found 9/14$206
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/185:05 amORD - BDL
1 stop10h 07mMultiple Airlines
Mon 10/206:36 pmBDL - ORD
2 stops24h 17mMultiple Airlines
Deal found 9/13$207
This Kiwi.com deal was found by Cheapflights users on 9/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/107:43 pmORD - BDL
1 stop19h 29mSpirit Airlines
Mon 10/137:10 pmBDL - ORD
1 stop24h 28mSpirit Airlines
Deal found 9/12$208
This Priceline deal was found by Cheapflights users on 9/14. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/245:05 amORD - BDL
1 stop9h 01mFrontier
Mon 10/274:01 pmBDL - ORD
1 stop8h 38mFrontier
Deal found 9/14$209

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Springfield 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 September 15, 2025.
Use the filters below to find and compare flights from Chicago to Springfield that are best for you.

Fly from

Chicago

Fly to

Springfield

Route

Depart

Return

Price

ChicagoHartford

MDW - BDL

MDWBDL

Chicago Midway

Thu 11/6

9:05 pm-8:05 am

1 stop10h 00m

Hartford Bradley Intl

Sun 11/9

3:35 pm-11:10 pm

1 stop8h 35m

$182

ChicagoHartford

ORD - BDL

ORDBDL

Chicago O'Hare Intl

Wed 10/1

4:00 pm-11:57 pm

1 stop6h 57m

Hartford Bradley Intl

Fri 10/3

7:53 pm-11:15 pm

1 stop4h 22m

$185

ChicagoHartford

ORD - BDL

ORDBDL

Chicago O'Hare Intl

Tue 9/30

7:20 am-1:31 pm

1 stop5h 11m

Hartford Bradley Intl

Tue 10/7

5:30 am-9:43 am

1 stop5h 13m

$197

ChicagoHartford

ORD - BDL

ORDBDL

Chicago O'Hare Intl

Fri 10/3

9:10 am-4:13 pm

1 stop6h 03m

Hartford Bradley Intl

Sun 10/5

5:35 am-10:19 am

1 stop5h 44m

$197

ChicagoHartford

ORD - BDL

ORDBDL

Chicago O'Hare Intl

Thu 11/6

11:01 am-2:11 pm

Nonstop2h 10m

Hartford Bradley Intl

Sun 11/9

6:10 am-8:02 am

Nonstop2h 52m

$202

ChicagoHartford

ORD - BDL

ORDBDL

Chicago O'Hare Intl

Fri 10/24

5:05 am-3:06 pm

1 stop9h 01m

Hartford Bradley Intl

Mon 10/27

4:01 pm-11:39 pm

1 stop8h 38m

$213

ChicagoHartford

ORD - BDL

ORDBDL

Chicago O'Hare Intl

Fri 10/17

7:51 pm-1:44 pm

1 stop16h 53m

Hartford Bradley Intl

Mon 10/20

6:36 pm-5:53 pm

2 stops24h 17m

$219

ChicagoHartford

MDW - BDL

MDWBDL

Chicago Midway

Thu 11/6

7:25 pm-10:25 pm

Nonstop2h 00m

Hartford Bradley Intl

Sat 11/8

5:15 pm-6:45 pm

Nonstop2h 30m

$225

ChicagoHartford

ORD - BDL

ORDBDL

Chicago O'Hare Intl

Fri 10/3

6:00 am-7:57 pm

2 stops12h 57m

Hartford Bradley Intl

Sun 10/5

8:37 pm-4:17 pm

2 stops20h 40m

$240

ChicagoHartford

ORD - BDL

ORDBDL

Chicago O'Hare Intl

Fri 10/10

7:43 pm-4:12 pm

1 stop19h 29m

Hartford Bradley Intl

Sun 10/12

8:31 pm-9:22 am

1 stop13h 51m

$241

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/13

Showing 1-10 of 35 results
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Best time to book a flight from Chicago to Springfield

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

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

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Springfield. Price data was last updated on September 12, 2025.

To ensure you get the cheapest price possible for a flight from Chicago to Springfield, you should look to book at least 64 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.

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

Reviews of airlines servicing Springfield

Get insights into the airlines that provide service to Springfield. 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 Springfield. Reviews last updated September 15, 2025.
Read reviews from past customers who have flown Southwest, United Airlines, and American Airlines from Chicago to Springfield. 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.
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Overall

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Overall

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,929 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Overall

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Overall

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Frontier
5.8
Fair
3,172 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Overall

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Related info for your journey

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

  • How long is the flight from Chicago to Springfield?

    A quick flight from Chicago to Springfield can take about 5h 11m. Southwest provides one of the quickest options available for as low as $197. Chicago and Springfield are separated by a distance of 780 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

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

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

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

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

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

See more FAQs

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