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Cheap flights from Springfield, MA, MA to Chicago (CHI)

— CHI
Dec 5 — Dec 121
Sat 12/5
Sat 12/12
1 adult, Economy
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Cheapflights Tip: The best prices from Springfield to Chicago are usually found in January or December, booked 68 days in advance, depart on a Wednesday or Saturday and return on a Saturday

Find flight deals from Springfield to Chicago

Popular in

July

Cheapest in

January

Average price

$402
Highest demand for flights based on searches. 7% potential increase in price ($31 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in November 2026
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Reviews of airlines servicing Chicago

Read reviews from past customers who have flown Southwest,Delta, andUnited 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
4,214 reviews

Crew

8.6

Overall

8.0

Comfort

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
Southwest
8.0
Very good
4,214 reviews
Southwest
8.0
Very good
4,214 reviews

Crew

8.6

Overall

8.0

Comfort

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
Delta
7.8
Good
8,700 reviews
Southwest
8.0
Very good
4,214 reviews

Crew

8.6

Overall

8.0

Comfort

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
United Airlines
7.3
Good
10,462 reviews
Southwest
8.0
Very good
4,214 reviews

Crew

8.6

Overall

8.0

Comfort

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
JetBlue
7.1
Good
3,064 reviews
Southwest
8.0
Very good
4,214 reviews

Crew

8.6

Overall

8.0

Comfort

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
American Airlines
7.0
Good
12,228 reviews
Southwest
8.0
Very good
4,214 reviews

Crew

8.6

Overall

8.0

Comfort

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers

Related info for your journey

  • 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 $84 on JetBlue. Other airlines that offer cheap prices include Frontier from $121 and Southwest from $134 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
Benton Harbor
Merrillville
Lansing
Valparaiso
Hammond
Saint Joseph
Porter

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