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$99+ Cheap flights from Springfield, MA, MA 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 12/9. 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 Springfield to Chicago are usually found in August or September, booked 57 days in advance, depart on a Thursday or Wednesday and return on a Saturday

Cheap flight deals from Springfield to Chicago

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

Round-trip from

$188
(Frontier)

One-way from

$99
(Delta)

Popular in

April

Cheapest in

August

Average price

$317
From Springfield to Chicago (CHI)
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One-way flight from Springfield to Chicago (CHI)
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Highest demand for flights based on searches. 5% potential increase in price ($18 potential increase over avg. RT price).
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Cheapest flight prices on average. 0% potential price decrease ($4 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 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 September 15, 2025.

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.
Thu 10/166:38 pmBDL - ORD
Nonstop2h 43mUnited Airlines
Tue 10/2111:15 amORD - BDL
Nonstop2h 18mUnited Airlines
Deal found 9/12$186
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/2112:18 pmBDL - MDW
1 stop12h 02mFrontier
Mon 9/228:19 amMDW - BDL
1 stop10h 38mFrontier
Deal found 9/15$188
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.
Mon 10/67:10 pmBDL - ORD
1 stop24h 28mSpirit Airlines
Sat 10/115:05 amORD - BDL
1 stop10h 07mSpirit Airlines
Deal found 9/15$188
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1610:04 amBDL - ORD
2 stops15h 22mFrontier
Mon 10/205:05 amORD - BDL
1 stop9h 16mFrontier
Deal found 9/14$190
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/910:59 amBDL - MDW
1 stop12h 04mFrontier
Sat 11/1511:36 amMDW - BDL
2 stops21h 06mFrontier
Deal found 9/14$192
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 10/67:10 pmBDL - ORD
1 stop24h 28mMultiple Airlines
Wed 10/83:12 pmORD - BDL
1 stop16h 57mMultiple Airlines
Deal found 9/14$192
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.
Mon 11/101:36 pmBDL - MDW
2 stops23h 02mFrontier
Fri 11/141:37 pmMDW - BDL
1 stop19h 40mFrontier
Deal found 9/15$194
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/55:35 amBDL - MDW
1 stop4h 05mDelta
Tue 10/76:23 pmMDW - BDL
1 stop3h 51mDelta
Deal found 9/14$197
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/55:35 amBDL - ORD
1 stop5h 44mDelta
Tue 10/77:10 amORD - BDL
1 stop3h 59mDelta
Deal found 9/14$197
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/116:00 amBDL - ORD
Nonstop2h 52mUnited Airlines
Sun 12/1411:06 amORD - BDL
Nonstop2h 10mUnited Airlines
Deal found 9/15$198
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/147:10 amBDL - ORD
1 stop6h 12mJetBlue
Tue 10/211:35 pmORD - BDL
1 stop7h 54mJetBlue
Deal found 9/15$199
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/210:30 amBDL - MDW
1 stop6h 28mFrontier
Mon 10/68:19 amMDW - BDL
1 stop10h 38mFrontier
Deal found 9/14$201

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

Fly from

Springfield

Fly to

Chicago

Route

Depart

Return

Price

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Thu 10/16

6:38 pm-8:21 pm

Nonstop2h 43m

Chicago O'Hare Intl

Tue 10/21

11:15 am-2:33 pm

Nonstop2h 18m

$186

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Sun 10/5

5:35 am-8:40 am

1 stop4h 05m

Chicago Midway

Tue 10/7

6:23 pm-11:14 pm

1 stop3h 51m

$197

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Fri 10/24

7:10 pm-11:58 pm

1 stop5h 48m

Chicago O'Hare Intl

Wed 10/29

6:45 am-1:17 pm

1 stop5h 32m

$197

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Fri 10/31

5:30 am-9:43 am

1 stop5h 13m

Chicago O'Hare Intl

Tue 11/4

5:20 am-1:17 pm

1 stop6h 57m

$197

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Sun 10/5

5:35 am-10:19 am

1 stop5h 44m

Chicago O'Hare Intl

Tue 10/7

5:20 am-11:37 am

1 stop5h 17m

$197

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Tue 10/14

7:53 pm-11:15 pm

1 stop4h 22m

Chicago O'Hare Intl

Tue 10/21

2:15 pm-5:32 pm

Nonstop2h 17m

$235

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Sat 10/25

5:00 pm-11:58 pm

1 stop7h 58m

Chicago O'Hare Intl

Tue 10/28

8:55 am-4:09 pm

1 stop6h 14m

$255

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Sun 10/5

5:45 am-7:10 am

Nonstop2h 25m

Chicago Midway

Tue 10/7

7:55 am-3:40 pm

1 stop6h 45m

$257

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Sat 10/18

6:00 am-9:36 am

1 stop4h 36m

Chicago O'Hare Intl

Sun 10/19

7:32 am-10:51 am

Nonstop2h 19m

$260

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Wed 10/15

6:00 am-7:43 am

Nonstop2h 43m

Chicago O'Hare Intl

Thu 10/16

7:32 am-10:51 am

Nonstop2h 19m

$266

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 57 results
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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

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

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

To ensure you get the cheapest price possible for a flight from Springfield to Chicago, you should look to book at least 57 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 Springfield to Chicago?

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 September 15, 2025.
Read reviews from past customers who have flown Southwest, Delta, and United 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.
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

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
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

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
Delta
8.0
Very good
7,954 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

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
8,929 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

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
10,000 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

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
3,172 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

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 Springfield to Chicago. 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 Springfield to Chicago?

    For as low as $257, United Airlines can have you in Chicago from Springfield in 2h 25m. Springfield and Chicago are separated by a distance of 773 mi. This flight may include one or multiple stops.

  • What are the most popular routes from Springfield to Chicago?

    The most popular flight routes from Springfield to Chicago are Hartford Bradley Intl - Chicago O'Hare Intl, Hartford Bradley Intl - Chicago Midway and Hartford Bradley Intl - Chicago Greater Rockford.

  • 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 $245). Flying from Springfield to Chicago in March is currently the most expensive (average of $321). 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
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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