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$110+ 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 1/18. Fares are subject to change and may not be available on all flights or dates of travel.
CHI
Dec 3 — Dec 101
Wed 12/3
Wed 12/10
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 Tuesday and return on a Wednesday

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 November 3, 2025.

This Booking.com deal was found by Cheapflights users on 11/2. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/206:23 pmORD - BDL
1 stop21h 54mFrontier
Fri 12/511:59 amBDL - ORD
1 stop11h 25mFrontier
Deal found 11/2$166
This Booking.com deal was found by Cheapflights users on 11/1. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/43:10 pmMDW - BDL
1 stop20h 14mFrontier
Sun 12/712:48 pmBDL - MDW
1 stop10h 24mFrontier
Deal found 11/1$166
This Southwest deal was found by Cheapflights users on 11/1. 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 12/46:40 amMDW - BDL
1 stop4h 20mSouthwest
Sun 12/77:15 pmBDL - MDW
Nonstop2h 30mSouthwest
Deal found 11/1$167
This Delta deal was found by Cheapflights users on 11/2. 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 12/46:00 amORD - BDL
1 stop7h 12mDelta
Sun 12/75:23 amBDL - ORD
1 stop5h 37mDelta
Deal found 11/2$177
This Delta deal was found by Cheapflights users on 11/2. 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 12/116:00 amMDW - BDL
1 stop6h 17mDelta
Thu 1/16:09 amBDL - MDW
1 stop5h 57mDelta
Deal found 11/2$177
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 12/61:24 pmORD - BDL
1 stop21h 06mFrontier
Mon 12/82:07 pmBDL - ORD
2 stops26h 05mFrontier
Deal found 11/2$186
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 12/1212:09 pmORD - BDL
2 stops9h 34mMultiple Airlines
Sun 12/142:03 pmBDL - ORD
1 stop24h 13mMultiple Airlines
Deal found 11/2$190
This American Airlines deal was found by Cheapflights users on 11/2. 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 12/48:35 pmORD - BDL
Nonstop2h 21mAmerican Airlines
Sun 12/75:52 amBDL - ORD
Nonstop3h 03mAmerican Airlines
Deal found 11/2$192
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 11/151:37 pmMDW - BDL
1 stop19h 05mFrontier
Sat 11/228:27 pmBDL - MDW
1 stop21h 03mFrontier
Deal found 11/1$192
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 12/131:24 pmORD - BDL
1 stop21h 06mMultiple Airlines
Mon 12/152:07 pmBDL - ORD
1 stop8h 41mMultiple Airlines
Deal found 11/2$194
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 12/53:52 pmMDW - BDL
1 stop21h 57mMultiple Airlines
Sun 12/712:48 pmBDL - MDW
1 stop6h 24mMultiple Airlines
Deal found 11/2$195
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 11/206:48 amORD - BDL
1 stop11h 44mMultiple Airlines
Fri 12/51:35 pmBDL - ORD
2 stops8h 07mMultiple Airlines
Deal found 11/2$204

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 November 3, 2025.

Round-trip from

$166
(Booking.com)

One-way from

$110
(Kiwi.com)

Popular in

December

Cheapest in

August

Average price

$388
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 ($37 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 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 November 3, 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

Thu 12/4

6:45 am-12:14 pm

1 stop4h 29m

Hartford Bradley Intl

Sun 12/7

9:43 am-1:50 pm

1 stop5h 07m

$177

ChicagoHartford

ORD - BDL

ORDBDL

Chicago O'Hare Intl

Sun 1/25

5:27 pm-11:40 pm

1 stop5h 13m

Hartford Bradley Intl

Sun 2/1

5:00 pm-11:57 pm

1 stop7h 57m

$177

ChicagoHartford

ORD - BDL

ORDBDL

Chicago O'Hare Intl

Thu 1/22

7:05 am-3:55 pm

1 stop7h 50m

Hartford Bradley Intl

Sun 1/25

5:30 am-9:40 am

1 stop5h 10m

$177

ChicagoHartford

ORD - BDL

ORDBDL

Chicago O'Hare Intl

Sat 1/31

7:05 am-1:42 pm

1 stop5h 37m

Hartford Bradley Intl

Sun 2/1

5:30 am-9:40 am

1 stop5h 10m

$177

ChicagoHartford

ORD - BDL

ORDBDL

Chicago O'Hare Intl

Thu 12/11

5:30 am-1:17 pm

1 stop6h 47m

Hartford Bradley Intl

Thu 1/1

5:30 am-9:01 am

1 stop4h 31m

$177

ChicagoHartford

MDW - BDL

MDWBDL

Chicago Midway

Thu 1/22

10:53 am-5:45 pm

1 stop5h 52m

Hartford Bradley Intl

Sun 1/25

5:00 pm-10:26 pm

1 stop6h 26m

$177

ChicagoHartford

MDW - BDL

MDWBDL

Chicago Midway

Sat 1/31

4:30 pm-10:34 pm

1 stop5h 04m

Hartford Bradley Intl

Sun 2/1

5:30 am-8:54 am

1 stop4h 24m

$177

ChicagoHartford

MDW - BDL

MDWBDL

Chicago Midway

Thu 12/11

6:00 am-1:17 pm

1 stop6h 17m

Hartford Bradley Intl

Thu 1/1

6:09 am-11:06 am

1 stop5h 57m

$177

ChicagoHartford

ORD - BDL

ORDBDL

Chicago O'Hare Intl

Wed 12/24

6:13 pm-9:35 pm

Nonstop2h 22m

Hartford Bradley Intl

Thu 1/1

6:15 pm-8:17 pm

Nonstop3h 02m

$227

ChicagoHartford

ORD - BDL

ORDBDL

Chicago O'Hare Intl

Wed 1/28

8:45 am-2:03 pm

1 stop4h 18m

Hartford Bradley Intl

Sun 2/1

9:55 am-11:46 am

Nonstop2h 51m

$235

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/2

Showing 1-10 of 43 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 October 31, 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 November 3, 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
4,238 reviews

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Crew

8.6

Overall

8.0

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
4,238 reviews
Southwest
8.0
Very good
4,238 reviews

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Crew

8.6

Overall

8.0

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
8,997 reviews
Southwest
8.0
Very good
4,238 reviews

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Crew

8.6

Overall

8.0

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
11,036 reviews
Southwest
8.0
Very good
4,238 reviews

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Crew

8.6

Overall

8.0

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
3,117 reviews
Southwest
8.0
Very good
4,238 reviews

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Crew

8.6

Overall

8.0

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 4h 29m. Delta provides one of the quickest options available for as low as $177. Chicago and Springfield are separated by a distance of 780 mi.

  • 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 $112. However, be on the lookout for offers from United Airlines and Southwest, 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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