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$59+ Cheap flights from Saint Paul, MN 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 11/13. Fares are subject to change and may not be available on all flights or dates of travel.
MSP — CHI
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
1 adult, Economy
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Cheapflights Tip: The best prices from Saint Paul to Chicago are usually found in November or September, booked 72 days in advance, depart on a Friday or Thursday and return on a Thursday

Cheap flight deals from Saint Paul to Chicago

Keep the following information in mind while searching for Saint Paul to Chicago flight deals. Data was last updated September 17, 2025.

Round-trip from

$92
(Sun Country Air)

One-way from

$59
(Southwest)

Popular in

February

Cheapest in

November

Average price

$158
From Saint Paul to Chicago (CHI)
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One-way flight from Saint Paul to Chicago (CHI)
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Highest demand for flights based on searches. 15% potential increase in price ($34 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($7 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 Saint Paul to Chicago

Cheapest flights from Saint Paul to Chicago
Explore the most affordable flight options available from Saint Paul to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 17, 2025.

This Sun Country Air deal was found by Cheapflights users on 9/17. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/295:00 pmMSP - ORD
Nonstop1h 38mSun Country Air
Tue 12/306:44 pmORD - MSP
Nonstop1h 39mSun Country Air
Deal found 9/17$92
This Southwest deal was found by Cheapflights users on 9/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/235:15 amMSP - MDW
Nonstop1h 30mSouthwest
Mon 10/277:45 amMDW - MSP
Nonstop1h 25mSouthwest
Deal found 9/16$97
This United Airlines deal was found by Cheapflights users on 9/17. 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.
Tue 10/146:00 amMSP - ORD
Nonstop1h 43mUnited Airlines
Wed 10/157:25 amORD - MSP
Nonstop1h 36mUnited Airlines
Deal found 9/17$97
This American Airlines deal was found by Cheapflights users on 9/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/235:00 amMSP - ORD
Nonstop1h 32mAmerican Airlines
Mon 10/277:36 amORD - MSP
Nonstop1h 39mAmerican Airlines
Deal found 9/16$98
This Delta deal was found by Cheapflights users on 9/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/306:59 amMSP - ORD
Nonstop1h 31mDelta
Mon 11/35:37 pmORD - MSP
Nonstop1h 38mDelta
Deal found 9/17$99
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/64:42 pmMSP - ORD
Nonstop1h 38mSun Country Air
Thu 11/67:20 pmORD - MSP
Nonstop1h 42mSun Country Air
Deal found 9/15$104
This Booking.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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/244:36 pmMSP - ORD
Nonstop1h 39mSun Country Air
Mon 10/2711:41 amORD - MSP
Nonstop1h 43mSun Country Air
Deal found 9/14$105
This Frontier deal was found by Cheapflights users on 9/16. 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.
Fri 11/1411:29 amMSP - ORD
1 stop12h 42mFrontier
Fri 12/126:13 amORD - MSP
Nonstop1h 33mFrontier
Deal found 9/16$106
This Southwest deal was found by Cheapflights users on 9/17. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/115:45 amMSP - MDW
2 stops6h 45mSouthwest
Sat 11/225:55 pmMDW - MSP
Nonstop1h 30mSouthwest
Deal found 9/17$112
This Southwest deal was found by Cheapflights users on 9/17. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/305:15 amMSP - MDW
Nonstop1h 30mSouthwest
Mon 11/311:25 amMDW - MSP
1 stop10h 20mSouthwest
Deal found 9/17$113
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/73:36 pmMSP - ORD
Nonstop1h 38mSun Country Air
Mon 11/1011:45 amORD - MSP
Nonstop1h 42mSun Country Air
Deal found 9/15$114
This Sun Country Air deal was found by Cheapflights users on 9/17. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/144:48 pmMSP - ORD
Nonstop1h 38mSun Country Air
Mon 11/1711:42 amORD - MSP
Nonstop1h 42mSun Country Air
Deal found 9/17$115

Cheapflights Fare Finder

 
Customize your flight search to find flights from Saint Paul 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 17, 2025.
Use the filters below to find and compare flights from Saint Paul to Chicago that are best for you.

Fly from

Saint Paul

Fly to

Chicago

Route

Depart

Return

Price

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

Mon 11/24

8:54 am-10:39 am

Nonstop1h 45m

Chicago O'Hare Intl

Mon 12/1

9:18 am-11:00 am

Nonstop1h 42m

$92

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Tue 11/11

10:30 am-12:00 pm

Nonstop1h 30m

Chicago Midway

Sat 11/22

5:55 pm-7:25 pm

Nonstop1h 30m

$97

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Sat 11/8

8:50 am-10:30 am

Nonstop1h 40m

Chicago Midway

Sat 11/8

7:10 pm-8:49 pm

Nonstop1h 39m

$97

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

Wed 10/22

6:00 am-7:43 am

Nonstop1h 43m

Chicago O'Hare Intl

Sat 10/25

8:51 am-10:27 am

Nonstop1h 36m

$97

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

Sat 11/8

7:30 am-9:03 am

Nonstop1h 33m

Chicago O'Hare Intl

Sat 11/8

5:40 pm-7:12 pm

Nonstop1h 32m

$97

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

Thu 10/9

6:00 am-7:43 am

Nonstop1h 43m

Chicago O'Hare Intl

Sat 10/11

2:15 pm-3:50 pm

Nonstop1h 35m

$97

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

Wed 10/29

1:25 pm-2:55 pm

Nonstop1h 30m

Chicago O'Hare Intl

Tue 12/2

6:00 am-7:36 am

Nonstop1h 36m

$97

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

Mon 10/20

6:10 pm-7:43 pm

Nonstop1h 33m

Chicago O'Hare Intl

Tue 10/21

11:02 am-12:35 pm

Nonstop1h 33m

$97

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Tue 10/7

6:00 am-9:55 am

1 stop3h 55m

Chicago Midway

Tue 10/7

8:35 pm-10:00 pm

Nonstop1h 25m

$107

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Thu 10/23

11:30 am-1:00 pm

Nonstop1h 30m

Chicago Midway

Mon 10/27

6:55 pm-11:50 pm

1 stop4h 55m

$107

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 54 results
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Best time to book a flight from Saint Paul to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Saint Paul 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 Saint Paul to Chicago

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

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

Booking 72 days in advance of your planned departure date is, on average, the best time to get cheap flights from Saint Paul to Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

What is the cheapest month to book a flight from Saint Paul to Chicago?

Currently, August is the cheapest month in which you can book a flight from Saint Paul to Chicago (average of $245). Flying from Saint Paul 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.

What is the cheapest time of day to fly from SA1 to CHI?

Find hourly flight availability from Saint Paul to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 17, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Saint Paul to Chicago as you normally would.

What is the cheapest day to fly from Saint Paul to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Saint Paul to Chicago. Price data was last updated on September 14, 2025.

Travelers seeking maximum savings on their Saint Paul to Chicago flight should consider departing on Friday evenings when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Saint Paul to Chicago

Explore weekly flight availability from Saint Paul to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated September 17, 2025.

The most flights from SA1 to CHI are scheduled on a Monday (119 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (49 on average).

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 17, 2025.
Read through reviews of airlines operating flights from Saint Paul to Chicago, such as Southwest, Delta, and United Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Food

7.0

Comfort

8.0

Overall

8.0

Boarding

8.1

Crew

8.6

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

Entertainment

7.5

Food

7.0

Comfort

8.0

Overall

8.0

Boarding

8.1

Crew

8.6

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
7,961 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Food

7.0

Comfort

8.0

Overall

8.0

Boarding

8.1

Crew

8.6

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
8,926 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Food

7.0

Comfort

8.0

Overall

8.0

Boarding

8.1

Crew

8.6

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

Entertainment

7.5

Food

7.0

Comfort

8.0

Overall

8.0

Boarding

8.1

Crew

8.6

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
Sun Country Air
6.9
Okay
330 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Food

7.0

Comfort

8.0

Overall

8.0

Boarding

8.1

Crew

8.6

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 Saint Paul 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 Saint Paul to Chicago?

    For as low as $97, Sun Country Air can have you in Chicago from Saint Paul in 1h 30m. There are 348 mi between Saint Paul and Chicago. Most flights are nonstop.

  • What are the most popular routes from Saint Paul to Chicago?

    The most popular flight routes from Saint Paul to Chicago are Minneapolis St Paul - Chicago O'Hare Intl, Minneapolis St Paul - Chicago Midway and Minneapolis St Paul - Chicago Greater Rockford.

  • What are the most reliable airlines from Saint Paul to Chicago?

    No one likes to see their flight delayed. When booking a flight from Saint Paul to Chicago consider choosing SkyWest Airlines (90%), Turkish Airlines (89%) or Avianca (85%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Saint Paul to Chicago?

    While on average a flight from Saint Paul to Chicago is generally $755, our data shows the cheapest flight currently is $60. When looking at the most popular route, (Minneapolis St Paul - Chicago O'Hare Intl), you can expect to pay $92 for that flight.

  • Can I find deals for flights from Saint Paul to Chicago that include hotel bookings?

    Yes. In addition to deals on Saint Paul to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Saint Paul to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Saint Paul to Chicago.

  • Can I find deals for business class flights from Saint Paul to Chicago?

    Yes. Cheapflights offers flight deals from Saint Paul 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 Saint Paul to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Saint Paul to Chicago (average of $245). Flying from Saint Paul 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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Alternative routes for Saint Paul to Chicago

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Top 5 airlines flying from Saint Paul to Chicago

Discover the top 5 airlines that operate flights from Saint Paul to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
Sun Country AirCheapest$68Average$158FlexibilityNo cancel feeOn-time83%
DeltaCheapest$72Average$329FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$91Average$293FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$93Average$223FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$97Average$222FlexibilityNo cancel feeOn-time63%

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