HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$109+ 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 1/29. Fares are subject to change and may not be available on all flights or dates of travel.
— CHI
Dec 2 — Dec 91
Tue 12/2
Tue 12/9
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Springfield to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheapflights Tip: The best prices from Springfield to Chicago are usually found in September or August, booked 66 days in advance, depart on a Wednesday or Thursday 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 November 2, 2025.

Round-trip from

$217
(Kiwi.com)

One-way from

$109
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$384
From Springfield to Chicago (CHI)
Search Deals
One-way flight from Springfield to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 3% potential increase in price ($14 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 November 2025
Search Deals

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 November 2, 2025.

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 12/121:30 pmBDL - MDW
2 stops10h 09mMultiple Airlines
Sun 12/146:37 pmMDW - BDL
1 stop17h 35mMultiple Airlines
Deal found 11/2$217
This Kiwi.com deal was found by Cheapflights users on 10/31. 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 11/177:36 pmBDL - ORD
2 stops21h 39mMultiple Airlines
Thu 11/206:48 amORD - BDL
1 stop11h 44mMultiple Airlines
Deal found 10/31$218
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 11/211:30 pmBDL - ORD
2 stops10h 36mMultiple Airlines
Mon 11/246:15 pmORD - BDL
1 stop24h 17mMultiple Airlines
Deal found 11/2$219
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.
Sun 11/161:36 pmBDL - MDW
1 stop19h 56mFrontier
Tue 11/256:15 pmMDW - BDL
2 stops48h 17mFrontier
Deal found 11/1$220
This Kiwi.com deal was found by Cheapflights users on 10/31. 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.
Sun 11/167:39 pmBDL - ORD
1 stop15h 08mMultiple Airlines
Wed 11/1912:37 pmORD - BDL
1 stop20h 15mMultiple Airlines
Deal found 10/31$220
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.
Fri 11/147:36 pmBDL - MDW
1 stop26h 46mFrontier
Wed 11/191:56 pmMDW - BDL
2 stops27h 21mFrontier
Deal found 11/1$221
This Kiwi.com deal was found by Cheapflights users on 10/30. 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 11/1511:13 amBDL - ORD
1 stop13h 16mMultiple Airlines
Thu 11/206:48 amORD - BDL
1 stop11h 44mMultiple Airlines
Deal found 10/30$221
This Kiwi.com deal was found by Cheapflights users on 10/31. 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 11/137:39 pmBDL - ORD
2 stops22h 23mMultiple Airlines
Thu 11/206:48 amORD - BDL
1 stop11h 44mMultiple Airlines
Deal found 10/31$224
This Kiwi.com deal was found by Cheapflights users on 10/31. 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 11/1511:13 amBDL - ORD
1 stop13h 16mMultiple Airlines
Wed 11/192:31 pmORD - BDL
2 stops18h 21mMultiple Airlines
Deal found 10/31$225
This Kiwi.com deal was found by Cheapflights users on 10/30. 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 11/147:36 pmBDL - ORD
1 stop15h 11mMultiple Airlines
Wed 11/196:48 amORD - BDL
1 stop7h 01mMultiple Airlines
Deal found 10/30$226
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.
Fri 12/1211:59 amBDL - MDW
1 stop11h 13mFrontier
Sun 12/146:37 pmMDW - BDL
1 stop17h 35mFrontier
Deal found 11/1$227
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 12/47:10 amBDL - ORD
2 stops28h 58mMultiple Airlines
Sun 12/72:36 pmORD - BDL
1 stop21h 36mMultiple Airlines
Deal found 11/2$227

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 November 2, 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 1/10

4:46 pm-6:36 pm

Nonstop2h 50m

Chicago O'Hare Intl

Sun 1/11

11:04 am-2:22 pm

Nonstop2h 18m

$227

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Mon 2/23

4:43 pm-6:35 pm

Nonstop2h 52m

Chicago O'Hare Intl

Thu 2/26

7:15 am-10:33 am

Nonstop2h 18m

$227

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Thu 12/4

5:15 am-6:45 am

Nonstop2h 30m

Chicago Midway

Mon 12/8

6:15 pm-9:25 pm

Nonstop2h 10m

$242

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Tue 12/30

5:30 am-8:49 am

1 stop4h 19m

Chicago Midway

Tue 1/6

6:14 pm-11:40 pm

1 stop4h 26m

$280

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Fri 1/16

6:00 am-9:43 am

1 stop4h 43m

Chicago O'Hare Intl

Sun 1/18

6:25 pm-9:48 pm

Nonstop2h 23m

$281

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Sun 11/16

6:05 am-1:07 pm

1 stop8h 02m

Chicago Midway

Tue 11/18

6:00 am-1:20 pm

1 stop6h 20m

$287

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Sun 11/16

5:30 am-10:01 am

1 stop5h 31m

Chicago O'Hare Intl

Tue 11/18

10:46 am-4:27 pm

1 stop4h 41m

$287

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Fri 12/12

4:50 pm-11:00 pm

1 stop7h 10m

Chicago Midway

Sun 12/14

7:25 pm-10:25 pm

Nonstop2h 00m

$295

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Fri 12/12

6:00 am-9:36 am

1 stop4h 36m

Chicago O'Hare Intl

Sun 12/14

6:13 pm-9:31 pm

Nonstop2h 18m

$295

HartfordChicago

BDL - ORD

BDLORD

Hartford Bradley Intl

Thu 12/25

6:00 am-9:38 am

1 stop4h 38m

Chicago O'Hare Intl

Sun 12/28

10:58 am-2:16 pm

Nonstop2h 18m

$295

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/2

Showing 1-10 of 52 results
1
2
3
...
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 October 31, 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 November 2, 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
8.0
Very good
4,241 reviews

Boarding

8.1

Crew

8.6

Food

7.0

Entertainment

7.5

Overall

8.0

Comfort

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
4,241 reviews
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Crew

8.6

Food

7.0

Entertainment

7.5

Overall

8.0

Comfort

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
8,993 reviews
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Crew

8.6

Food

7.0

Entertainment

7.5

Overall

8.0

Comfort

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
11,032 reviews
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Crew

8.6

Food

7.0

Entertainment

7.5

Overall

8.0

Comfort

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
JetBlue
7.2
Good
2,907 reviews
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Crew

8.6

Food

7.0

Entertainment

7.5

Overall

8.0

Comfort

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
3,119 reviews
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Crew

8.6

Food

7.0

Entertainment

7.5

Overall

8.0

Comfort

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 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 $242, United Airlines can have you in Chicago from Springfield in 2h 30m. Springfield and Chicago are separated by a distance of 773 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 $144 on Delta. Other airlines that offer cheap prices include Southwest from $147 and United Airlines from $157 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
Merrillville
Lansing
Hammond
Porter
Benton Harbor

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Springfield to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Boston to O'Hare Intl flights
Hartford to O'Hare Intl flights
Boston to Midway flights
Boston to St. Louis flights
Hartford to Midway flights
Albany to O'Hare Intl flights
Albany to Midway flights
Hartford to St. Louis flights
Boston to Moline flights
Albany to St. Louis flights
Worcester to O'Hare Intl flights
Hyannis to O'Hare Intl flights
Boston to Peoria flights
Boston to Bloomington flights
Hartford to Moline flights
Boston to Dubuque flights
Albany to Evansville flights
Boston to Evansville flights
Hartford to Peoria flights
Boston to Rockford flights
Hartford to Rockford flights
Boston to Champaign flights
Hartford to Springfield flights
Boston to Paducah flights
Albany to Moline flights
Boston to Springfield flights
Albany to Peoria flights
Hartford to Evansville flights
Albany to Springfield flights
West Tisbury to O'Hare Intl flights
Boston to Decatur flights
Hartford to Bloomington flights
Albany to Champaign flights
Nantucket to O'Hare Intl flights
Provincetown to O'Hare Intl flights
Boston to Burlington flights
West Tisbury to St. Louis flights
New Bedford to O'Hare Intl flights

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.