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$68+ 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 1/12. 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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Cheapflights Tip: The best prices from Springfield to Chicago are usually found in October or September, booked 66 days in advance, depart on a Wednesday or Thursday and return on a Saturday

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 December 18, 2025.

This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/244:47 pmBDL - MDW
1 stop6h 35mDelta
Thu 1/16:00 amMDW - BDL
1 stop6h 14mDelta
Deal found 12/15$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.
Thu 12/255:30 amBDL - ORD
1 stop4h 31mDelta
Thu 12/255:31 pmORD - BDL
1 stop5h 05mDelta
Deal found 12/16$177
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/257:40 pmBDL - ORD
1 stop5h 04mUnited Airlines
Thu 1/17:10 amORD - BDL
Nonstop2h 26mUnited Airlines
Deal found 12/16$222
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/317:40 pmBDL - ORD
1 stop5h 04mUnited Airlines
Tue 1/66:06 pmORD - BDL
Nonstop2h 23mUnited Airlines
Deal found 12/16$235
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/247:40 pmBDL - ORD
1 stop5h 04mUnited Airlines
Thu 12/256:13 pmORD - BDL
Nonstop2h 22mUnited Airlines
Deal found 12/16$238
This Booking.com 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/308:04 pmBDL - ORD
1 stop15h 14mFrontier
Thu 1/111:28 amORD - BDL
1 stop6h 49mFrontier
Deal found 12/15$272
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:15 amBDL - ORD
Nonstop2h 50mUnited Airlines
Thu 1/12:05 pmORD - BDL
Nonstop2h 24mUnited Airlines
Deal found 12/17$298
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1812:05 pmBDL - MDW
1 stop11h 07mFrontier
Mon 12/226:15 amMDW - BDL
1 stop8h 14mFrontier
Deal found 12/16$322
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.
Tue 12/2312:05 pmBDL - MDW
1 stop11h 07mFrontier
Mon 12/296:15 amMDW - BDL
1 stop8h 14mFrontier
Deal found 12/15$372
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.
Sun 12/2112:05 pmBDL - MDW
1 stop11h 07mFrontier
Mon 12/296:15 amMDW - BDL
1 stop8h 14mFrontier
Deal found 12/15$377
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/244:47 pmBDL - MDW
1 stop6h 35mDelta
Fri 1/29:29 amMDW - BDL
1 stop5h 53mDelta
Deal found 12/15$384
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/244:47 pmBDL - MDW
1 stop6h 35mDelta
Wed 12/3111:48 amMDW - BDL
2 stops24h 26mDelta
Deal found 12/15$409

Find flight deals from Springfield to Chicago

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

Round-trip from

$170
(Kiwi.com)

One-way from

$68
(Kiwi.com)

Popular in

May

Cheapest in

October

Average price

$367
From Springfield to Chicago (CHI)
Search Deals
One-way flight from Springfield to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($42 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 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 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 December 18, 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

Sat 1/17

4:46 pm-6:36 pm

Nonstop2h 50m

Chicago O'Hare Intl

Sun 1/18

6:17 pm-11:44 pm

1 stop4h 27m

$167

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Thu 1/8

6:05 am-9:43 am

1 stop28h 38m

Chicago O'Hare Intl

Sun 1/11

8:27 pm-7:24 pm

1 stop21h 57m

$231

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Thu 1/15

11:46 am-10:44 pm

1 stop11h 58m

Chicago O'Hare Intl

Sun 1/18

7:45 am-11:48 pm

2 stops15h 03m

$234

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Mon 2/23

10:52 am-8:32 pm

1 stop10h 40m

Chicago Midway

Thu 2/26

7:30 am-5:05 pm

1 stop8h 35m

$242

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Tue 2/10

12:19 pm-7:41 pm

1 stop8h 22m

Chicago O'Hare Intl

Thu 2/12

11:51 am-5:29 pm

2 stops28h 38m

$243

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Wed 1/14

5:40 am-8:52 am

1 stop4h 12m

Chicago Midway

Sat 1/17

6:45 am-1:33 pm

1 stop5h 48m

$245

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Wed 2/11

4:55 pm-9:05 pm

1 stop5h 10m

Chicago O'Hare Intl

Sat 2/14

6:45 am-1:41 pm

1 stop5h 56m

$245

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Wed 12/31

7:40 pm-11:44 pm

1 stop5h 04m

Chicago O'Hare Intl

Tue 1/6

6:17 pm-11:44 pm

1 stop4h 27m

$245

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Sat 2/14

5:33 pm-11:57 pm

1 stop7h 24m

Chicago O'Hare Intl

Tue 2/17

5:37 pm-11:39 pm

1 stop5h 02m

$245

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Thu 1/22

6:00 am-5:43 pm

2 stops12h 43m

Chicago O'Hare Intl

Sun 1/25

7:45 am-11:48 pm

2 stops15h 03m

$254

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/17

Showing 1-10 of 54 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 December 12, 2025.

To ensure you get the cheapest price possible for a flight from Springfield to Chicago, you should look to book at least 66 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 December 18, 2025.
Read reviews from past customers who have flown Southwest, 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.
Southwest
7.9
Good
4,252 reviews

Entertainment

7.5

Boarding

8.1

Overall

7.9

Food

7.0

Crew

8.6

Comfort

8.0

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
4,252 reviews
Southwest
7.9
Good
4,252 reviews

Entertainment

7.5

Boarding

8.1

Overall

7.9

Food

7.0

Crew

8.6

Comfort

8.0

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
9,095 reviews
Southwest
7.9
Good
4,252 reviews

Entertainment

7.5

Boarding

8.1

Overall

7.9

Food

7.0

Crew

8.6

Comfort

8.0

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
4,252 reviews

Entertainment

7.5

Boarding

8.1

Overall

7.9

Food

7.0

Crew

8.6

Comfort

8.0

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
JetBlue
7.2
Good
2,896 reviews
Southwest
7.9
Good
4,252 reviews

Entertainment

7.5

Boarding

8.1

Overall

7.9

Food

7.0

Crew

8.6

Comfort

8.0

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
Frontier
5.8
Fair
3,080 reviews
Southwest
7.9
Good
4,252 reviews

Entertainment

7.5

Boarding

8.1

Overall

7.9

Food

7.0

Crew

8.6

Comfort

8.0

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 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 $167, United Airlines can have you in Chicago from Springfield in 2h 50m. Springfield and Chicago are separated by a distance of 780 mi. This flight may include one or multiple stops.

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

    One-way options have recently been found by users for as low as $68 on Southwest. Other airlines that offer cheap prices include Frontier from $77 and American Airlines from $78 one-way.

  • 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.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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