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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 4/10. Fares are subject to change and may not be available on all flights or dates of travel.
MSP — CHI
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Cheapflights Tip: The best prices from Saint Paul to Chicago are usually found in September or October, booked 56 days in advance, depart on a Friday or Thursday and return on a Thursday

Cheap 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 December 18, 2025.

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 12/245:18 pmMSP - ORD
Nonstop1h 37mUnited Airlines
Thu 12/259:05 pmORD - MSP
Nonstop1h 39mUnited Airlines
Deal found 12/16$143
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/304:06 pmMSP - ORD
Nonstop1h 38mSun Country Air
Fri 1/211:51 amORD - MSP
Nonstop1h 39mSun Country Air
Deal found 12/16$154
This Orbitz 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/262:57 pmMSP - ORD
Nonstop1h 45mFrontier
Thu 1/152:30 pmORD - MSP
1 stop9h 27mFrontier
Deal found 12/16$168
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/315:18 pmMSP - ORD
Nonstop1h 37mUnited Airlines
Tue 1/67:15 amORD - MSP
Nonstop1h 33mUnited Airlines
Deal found 12/15$169
This Kiwi.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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/2210:09 pmMSP - ORD
Nonstop1h 45mFrontier
Mon 1/57:00 amORD - MSP
1 stop13h 51mFrontier
Deal found 12/15$173
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/315:18 pmMSP - ORD
Nonstop1h 37mUnited Airlines
Thu 1/13:58 pmORD - MSP
Nonstop1h 31mUnited Airlines
Deal found 12/15$174
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.
Wed 12/249:10 amMSP - MDW
Nonstop1h 56mDelta
Thu 12/2511:48 amMDW - MSP
Nonstop1h 44mDelta
Deal found 12/16$178
This Orbitz 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/2910:09 pmMSP - ORD
Nonstop1h 45mMultiple Airlines
Thu 1/16:14 pmORD - MSP
Nonstop1h 39mMultiple Airlines
Deal found 12/16$179
This Super.com 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/262:57 pmMSP - ORD
Nonstop1h 45mFrontier
Mon 12/297:38 pmORD - MSP
Nonstop1h 36mFrontier
Deal found 12/16$187
This Sun Country Air 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/185:30 pmMSP - ORD
Nonstop1h 38mSun Country Air
Wed 12/3111:45 amORD - MSP
Nonstop1h 39mSun Country Air
Deal found 12/16$188
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.
Mon 12/2210:09 pmMSP - ORD
Nonstop1h 45mFrontier
Mon 12/297:38 pmORD - MSP
Nonstop1h 36mFrontier
Deal found 12/16$194
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/315:30 amMSP - MDW
1 stop5h 55mSouthwest
Thu 1/11:45 pmMDW - MSP
Nonstop1h 30mSouthwest
Deal found 12/17$240

Find 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 December 18, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$92
(Booking.com)

One-way from

$59
(Mytrip)

Popular in

February

Cheapest in

September

Average price

$163
Provider with most accurate pricing for Minneapolis St Paul-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Minneapolis St Paul-Chicago (CHI) flights.
Search Deals
From Saint Paul to Chicago (CHI)
Search Deals
One-way flight from Saint Paul to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 15% potential increase in price ($32 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($7 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 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 December 18, 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 - MDW

MSPMDW

Minneapolis St Paul

Wed 1/14

4:50 pm-6:32 pm

Nonstop1h 42m

Chicago Midway

Wed 1/21

9:50 am-11:34 am

Nonstop1h 44m

$133

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Tue 1/13

2:30 pm-9:50 pm

1 stop7h 20m

Chicago Midway

Tue 1/20

8:40 am-10:20 am

Nonstop1h 40m

$143

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

Sat 1/24

11:20 am-12:59 pm

Nonstop1h 39m

Chicago O'Hare Intl

Tue 1/27

8:18 pm-9:57 pm

Nonstop1h 39m

$152

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Sat 1/24

9:10 am-11:05 am

Nonstop1h 55m

Chicago Midway

Tue 1/27

1:49 pm-3:37 pm

Nonstop1h 48m

$152

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

Tue 2/24

5:13 pm-6:54 pm

Nonstop1h 41m

Chicago O'Hare Intl

Thu 2/26

2:15 pm-3:50 pm

Nonstop1h 35m

$152

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Tue 2/24

11:22 am-1:07 pm

Nonstop1h 45m

Chicago Midway

Thu 2/26

9:50 am-11:32 am

Nonstop1h 42m

$152

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

Tue 1/6

6:50 am-12:15 pm

1 stop5h 25m

Chicago O'Hare Intl

Wed 1/7

1:45 pm-8:35 pm

1 stop6h 50m

$153

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

Mon 1/12

5:16 pm-6:55 pm

Nonstop1h 39m

Chicago O'Hare Intl

Sat 2/21

3:56 pm-5:28 pm

Nonstop1h 32m

$171

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Thu 1/22

7:05 am-9:08 am

Nonstop2h 03m

Chicago Midway

Mon 1/26

9:50 am-11:34 am

Nonstop1h 44m

$171

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

Sat 1/24

2:30 pm-4:16 pm

Nonstop1h 46m

Chicago Midway

Mon 1/26

1:49 pm-3:37 pm

Nonstop1h 48m

$171

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/15

Showing 1-10 of 60 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 December 12, 2025.

Booking 56 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, April is the cheapest month in which you can book a flight from Saint Paul to Chicago (average of $54). Flying from Saint Paul to Chicago in July is currently the most expensive (average of $116). 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 December 18, 2025.

One of the essential ways to save on airfare from Saint Paul to Chicago is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the evening could potentially save you up to 41% on airfare.

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 December 13, 2025.

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

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 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
7.9
Good
4,251 reviews

Food

7.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Overall

7.9

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
4,251 reviews
Southwest
7.9
Good
4,251 reviews

Food

7.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Overall

7.9

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
Delta
7.9
Good
8,009 reviews
Southwest
7.9
Good
4,251 reviews

Food

7.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Overall

7.9

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
4,251 reviews

Food

7.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Overall

7.9

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
4,251 reviews

Food

7.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Overall

7.9

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
Sun Country Air
6.9
Okay
333 reviews
Southwest
7.9
Good
4,251 reviews

Food

7.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Overall

7.9

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 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 $152, Delta can have you in Chicago from Saint Paul in 1h 39m. There are 333 mi between Saint Paul and Chicago. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    The cheapest airline one-way is Frontier, with whom users have recently found tickets for as low as $27. However, be on the lookout for offers from Sun Country Air and Southwest, as they are both options that can get you from Saint Paul to Chicago for a low price.

  • 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 Copa Airlines (84%), Sun Country Air (83%) or ANA (75%) 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 $888, our data shows the cheapest flight currently is $49. 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, April is the cheapest month in which you can book a flight from Saint Paul to Chicago (average of $54). Flying from Saint Paul to Chicago in July is currently the most expensive (average of $116). 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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Top 6 airlines flying from Saint Paul to Chicago

Discover the top 6 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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$39Average$96FlexibilityNo cancel feeOn-time62%
Sun Country AirCheapest$68Average$158FlexibilityNo cancel feeOn-time83%
DeltaCheapest$69Average$319FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$97Average$302FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$97Average$220FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$103Average$221FlexibilityNo cancel feeOn-time63%

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