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Springfield

$81+ 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 2/19. Fares are subject to change and may not be available on all flights or dates of travel.
CHI
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Find cheap flights from Chicago to Springfield with Cheapflights

1. Tell us where you want to go

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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 Thursday and return on a Wednesday

Cheap 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 December 18, 2025.

This United Airlines deal was found by Cheapflights users on 12/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/246:21 pmORD - BDL
1 stop4h 37mUnited Airlines
Thu 1/16:15 pmBDL - ORD
Nonstop3h 02mUnited Airlines
Deal found 12/15$167
This Delta deal was found by Cheapflights users on 12/16. 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 12/246:45 amORD - BDL
1 stop7h 57mDelta
Thu 1/14:47 pmBDL - ORD
1 stop8h 15mDelta
Deal found 12/16$177
This Delta deal was found by Cheapflights users on 12/16. 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 12/246:08 pmMDW - BDL
1 stop4h 06mDelta
Thu 1/15:30 amBDL - MDW
1 stop4h 19mDelta
Deal found 12/16$177
This United Airlines deal was found by Cheapflights users on 12/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/258:50 amORD - BDL
1 stop4h 19mUnited Airlines
Thu 1/16:15 pmBDL - ORD
Nonstop3h 02mUnited Airlines
Deal found 12/15$237
This Frontier deal was found by Cheapflights users on 12/15. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/226:15 amMDW - BDL
1 stop8h 14mFrontier
Thu 1/112:05 pmBDL - MDW
1 stop11h 07mFrontier
Deal found 12/15$293
This United Airlines deal was found by Cheapflights users on 12/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/256:13 pmORD - BDL
Nonstop2h 22mUnited Airlines
Wed 12/316:15 amBDL - ORD
Nonstop2h 50mUnited Airlines
Deal found 12/15$298
This United Airlines deal was found by Cheapflights users on 12/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/246:21 pmORD - BDL
1 stop4h 37mUnited Airlines
Wed 12/316:15 amBDL - ORD
Nonstop2h 50mUnited Airlines
Deal found 12/15$308
This Expedia deal was found by Cheapflights users on 12/14. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/226:15 amMDW - BDL
1 stop8h 14mFrontier
Tue 12/308:04 pmBDL - MDW
1 stop26h 54mFrontier
Deal found 12/14$343
This Kiwi.com deal was found by Cheapflights users on 12/16. 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.
Wed 12/246:05 amORD - BDL
1 stop28h 05mMultiple Airlines
Sun 1/46:30 pmBDL - ORD
2 stops39h 01mMultiple Airlines
Deal found 12/16$344
This Kiwi.com deal was found by Cheapflights users on 12/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/311:34 pmORD - BDL
1 stop8h 12mMultiple Airlines
Sun 1/46:30 pmBDL - ORD
2 stops39h 01mMultiple Airlines
Deal found 12/17$372
This Southwest deal was found by Cheapflights users on 12/17. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/315:35 amMDW - BDL
1 stop8h 20mSouthwest
Sun 1/48:00 pmBDL - MDW
Nonstop2h 30mSouthwest
Deal found 12/17$380
This Delta deal was found by Cheapflights users on 12/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/246:02 pmORD - BDL
1 stop4h 12mDelta
Mon 12/296:55 pmBDL - ORD
1 stop6h 07mDelta
Deal found 12/14$384

Find flight deals from Chicago to Springfield

Keep the following information in mind while searching for Chicago to Springfield flight deals. Data was last updated December 18, 2025.

Round-trip from

$169
(Kiwi.com)

One-way from

$81
(Priceline)

Popular in

December

Cheapest in

August

Average price

$444
From Chicago (CHI) to Springfield
Search Deals
One-way flight from Chicago (CHI) to Springfield
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($36 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

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 December 18, 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

ORD - BDL

ORDBDL

Chicago O'Hare Intl

Sat 1/17

12:30 pm-8:08 pm

1 stop6h 38m

Hartford Bradley Intl

Sun 1/18

5:40 am-9:41 am

1 stop5h 01m

$177

ChicagoHartford

ORD - BDL

ORDBDL

Chicago O'Hare Intl

Wed 12/24

6:21 pm-11:58 pm

1 stop4h 37m

Hartford Bradley Intl

Thu 1/1

7:40 pm-11:44 pm

1 stop5h 04m

$177

ChicagoHartford

MDW - BDL

MDWBDL

Chicago Midway

Wed 12/24

6:08 pm-11:14 pm

1 stop4h 06m

Hartford Bradley Intl

Thu 1/1

5:30 am-8:49 am

1 stop4h 19m

$177

ChicagoHartford

MDW - BDL

MDWBDL

Chicago Midway

Sat 1/17

11:45 am-8:08 pm

1 stop7h 23m

Hartford Bradley Intl

Sun 1/18

5:40 am-8:52 am

1 stop4h 12m

$177

ChicagoHartford

MDW - BDL

MDWBDL

Chicago Midway

Thu 1/15

11:27 am-5:11 pm

1 stop28h 44m

Hartford Bradley Intl

Thu 1/22

12:11 pm-10:19 pm

1 stop11h 08m

$226

ChicagoHartford

ORD - BDL

ORDBDL

Chicago O'Hare Intl

Sat 1/17

11:04 am-2:22 pm

Nonstop2h 18m

Hartford Bradley Intl

Sun 1/18

4:46 pm-6:36 pm

Nonstop2h 50m

$228

ChicagoHartford

MDW - BDL

MDWBDL

Chicago Midway

Sat 1/17

9:55 am-7:20 pm

2 stops8h 25m

Hartford Bradley Intl

Sun 1/18

5:30 am-7:05 am

Nonstop2h 35m

$240

ChicagoHartford

MDW - BDL

MDWBDL

Chicago Midway

Wed 1/14

6:14 pm-11:40 pm

1 stop4h 26m

Hartford Bradley Intl

Sun 1/18

5:40 am-8:52 am

1 stop4h 12m

$245

ChicagoHartford

MDW - BDL

MDWBDL

Chicago Midway

Mon 12/22

6:15 am-3:29 pm

1 stop8h 14m

Hartford Bradley Intl

Thu 1/1

12:05 pm-10:12 pm

1 stop11h 07m

$293

ChicagoHartford

ORD - BDL

ORDBDL

Chicago O'Hare Intl

Fri 1/16

11:04 am-2:22 pm

Nonstop2h 18m

Hartford Bradley Intl

Sun 1/18

6:00 am-9:43 am

1 stop4h 43m

$295

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/17

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 December 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.

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 December 18, 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
7.9
Good
4,250 reviews

Overall

7.9

Boarding

8.1

Crew

8.6

Comfort

8.0

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
7.9
Good
4,250 reviews
Southwest
7.9
Good
4,250 reviews

Overall

7.9

Boarding

8.1

Crew

8.6

Comfort

8.0

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
United Airlines
7.4
Good
9,091 reviews
Southwest
7.9
Good
4,250 reviews

Overall

7.9

Boarding

8.1

Crew

8.6

Comfort

8.0

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
American Airlines
7.2
Good
11,054 reviews
Southwest
7.9
Good
4,250 reviews

Overall

7.9

Boarding

8.1

Crew

8.6

Comfort

8.0

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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 4h 37m. Delta provides one of the quickest options available for as low as $177. 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.

  • What are the cheapest airlines to fly from Chicago to Springfield one-way?

    The cheapest airline one-way is Frontier, with whom users have recently found tickets for as low as $52. However, be on the lookout for offers from Southwest and American Airlines, as they are both options that can get you from Chicago to Springfield for a low price.

  • 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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