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$70+ 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 4/16. Fares are subject to change and may not be available on all flights or dates of travel.
— CHI
Apr 24 — May 11
Fri 4/24
Fri 5/1
1 adult, Economy
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Cheapflights Tip: The best prices from Springfield to Chicago are usually found in January or October, booked 57 days in advance, depart on a Wednesday or Thursday and return on a Thursday

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 March 25, 2026.

This Southwest deal was found by Cheapflights users on 3/20. 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.
Tue 4/213:15 pm
BDL
-
MDW
1 stop5h 45m
Southwest
Wed 4/227:40 am
MDW
-
BDL
Nonstop2h 00m
Southwest
Deal found 3/20$327
This United Airlines deal was found by Cheapflights users on 3/20. 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.
Tue 4/216:00 am
BDL
-
ORD
1 stop6h 51m
United Airlines
Wed 4/226:45 am
ORD
-
BDL
Nonstop2h 18m
United Airlines
Deal found 3/20$327
This Priceline deal was found by Cheapflights users on 3/20. 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 6/1212:33 pm
BDL
-
ORD
1 stop11h 41m
Multiple Airlines
Mon 6/155:12 pm
ORD
-
BDL
1 stop5h 47m
Multiple Airlines
Deal found 3/20$328
This Kiwi.com deal was found by Cheapflights users on 3/22. 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 4/273:50 pm
BDL
-
MDW
1 stop7h 29m
Multiple Airlines
Wed 4/297:30 am
MDW
-
BDL
2 stops14h 39m
Multiple Airlines
Deal found 3/22$329
This CheapOair deal was found by Cheapflights users on 3/20. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/92:55 pm
BDL
-
ORD
1 stop8h 49m
Multiple Airlines
Tue 4/148:31 am
ORD
-
BDL
2 stops23h 19m
Multiple Airlines
Deal found 3/20$329
This Priceline deal was found by Cheapflights users on 3/22. 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 4/243:34 pm
BDL
-
MDW
1 stop7h 52m
Frontier
Sun 4/266:00 am
MDW
-
BDL
1 stop7h 49m
Frontier
Deal found 3/22$330
This Priceline deal was found by Cheapflights users on 3/22. 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.
Thu 4/163:50 pm
BDL
-
ORD
1 stop7h 49m
Frontier
Fri 4/175:59 am
ORD
-
BDL
1 stop7h 50m
Frontier
Deal found 3/22$330
This Kiwi.com deal was found by Cheapflights users on 3/22. 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 4/163:50 pm
BDL
-
MDW
1 stop7h 29m
Multiple Airlines
Tue 4/216:10 am
MDW
-
BDL
2 stops11h 01m
Multiple Airlines
Deal found 3/22$332
This Expedia deal was found by Cheapflights users on 3/23. 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.
Wed 7/1512:33 pm
BDL
-
ORD
1 stop11h 41m
Multiple Airlines
Sat 7/186:25 pm
ORD
-
BDL
1 stop15h 22m
Multiple Airlines
Deal found 3/23$332
This Southwest deal was found by Cheapflights users on 3/22. 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.
Tue 4/216:20 pm
BDL
-
MDW
Nonstop2h 30m
Southwest
Tue 4/287:40 am
MDW
-
BDL
Nonstop2h 00m
Southwest
Deal found 3/22$333
This Expedia deal was found by Cheapflights users on 3/23. 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.
Wed 3/256:00 am
BDL
-
ORD
1 stop6h 25m
Multiple Airlines
Sun 3/295:01 am
ORD
-
BDL
1 stop7h 43m
Multiple Airlines
Deal found 3/23$333
This Kiwi.com deal was found by Cheapflights users on 3/22. 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 4/243:34 pm
BDL
-
ORD
1 stop20h 59m
Multiple Airlines
Tue 4/2810:31 am
ORD
-
BDL
1 stop27h 34m
Multiple Airlines
Deal found 3/22$334

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 March 25, 2026.

Round-trip from

$327
(Southwest)

One-way from

$70
(Frontier)

Popular in

March

Cheapest in

January

Average price

$413
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 ($40 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
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 March 25, 2026.
Use the filters below to find and compare flights from Springfield to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Thu 5/7

12:40 pm-2:21 pm

Nonstop2h 41m

Chicago O'Hare Intl

Sat 5/9

12:55 pm-6:57 pm

1 stop5h 02m

$341

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Tue 5/5

3:04 pm-6:33 pm

1 stop4h 29m

Chicago O'Hare Intl

Wed 5/6

6:45 am-9:55 am

Nonstop2h 10m

$343
Quickest round-trip

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Mon 4/20

7:20 pm-8:45 pm

Nonstop2h 25m

Chicago Midway

Thu 4/23

7:40 am-10:40 am

Nonstop2h 00m

$346

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Wed 5/6

6:05 am-11:26 am

1 stop6h 21m

Chicago O'Hare Intl

Wed 5/6

4:25 pm-11:44 pm

1 stop6h 19m

$353

HartfordChicago

BDL - RFD

BDLRFD

Hartford Bradley Intl

Thu 8/20

7:02 am-3:09 pm

2 stops9h 07m

Chicago Greater Rockford

Mon 8/24

6:56 pm-2:45 pm

1 stop18h 49m

$357

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Thu 4/16

6:49 pm-8:50 pm

Nonstop3h 01m

Chicago O'Hare Intl

Tue 4/21

6:20 pm-9:37 pm

Nonstop2h 17m

$366

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Fri 6/5

6:00 am-11:53 am

1 stop6h 53m

Chicago O'Hare Intl

Mon 6/8

6:12 pm-11:59 pm

1 stop4h 47m

$382

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Mon 4/27

11:40 am-1:05 pm

Nonstop2h 25m

Chicago Midway

Wed 4/29

7:40 am-10:40 am

Nonstop2h 00m

$383

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Wed 7/8

12:55 pm-5:05 pm

1 stop5h 10m

Chicago Midway

Wed 7/8

6:45 pm-9:45 pm

Nonstop2h 00m

$393

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Tue 7/28

12:40 pm-2:05 pm

Nonstop2h 25m

Chicago Midway

Thu 7/30

1:30 pm-4:35 pm

Nonstop2h 05m

$408

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/24

Showing 1-10 of 60 resultsSorted by cheapest first
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6

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 March 13, 2026.

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 March 25, 2026.
Read reviews from past customers who have flown Southwest,United Airlines, andJetBlue 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
4,333 reviews

Overall

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
8.0
Very good
4,333 reviews
Southwest
8.0
Very good
4,333 reviews

Overall

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
United Airlines
7.4
Good
9,479 reviews
Southwest
8.0
Very good
4,333 reviews

Overall

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
JetBlue
7.2
Good
2,903 reviews
Southwest
8.0
Very good
4,333 reviews

Overall

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
American Airlines
7.1
Good
11,494 reviews
Southwest
8.0
Very good
4,333 reviews

Overall

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Frontier
5.7
Fair
3,017 reviews
Southwest
8.0
Very good
4,333 reviews

Overall

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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 $346, United Airlines can have you in Chicago from Springfield in 2h 25m. Springfield and Chicago are separated by a distance of 773 mi. All flights are typically nonstop.

  • 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 American Airlines from $78 and United Airlines from $103 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?

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Hammond
Porter
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