$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 4/17. Fares are subject to change and may not be available on all flights or dates of travel.
MSP — CHI
Jan 31 — Feb 71
1 adult, Economy
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Find cheap flights from Saint Paul 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 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 ChicagoExplore 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 January 1, 2026.
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 January 1, 2026.
This Kiwi.com deal was found by Cheapflights users on 12/30. 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.
Wed 12/318:54 amMSP - ORD
Nonstop1h 50mSun Country Air
Thu 1/16:14 pmORD - MSP
Nonstop1h 39mSun Country Air
Deal found 12/30![Sun Country Air logo]()
$253
This Frontier deal was found by Cheapflights users on 12/29. 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 12/2910:09 pmMSP - ORD
Nonstop1h 45mFrontier
Fri 1/212:26 pmORD - MSP
Nonstop1h 36mFrontier
Deal found 12/29![Frontier logo]()
$260
This United Airlines deal was found by Cheapflights users on 12/31. 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 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
Wed 12/319:15 pmORD - MSP
1 stop13h 40mUnited Airlines
Deal found 12/31![United Airlines logo]()
$307
This Kiwi.com deal was found by Cheapflights users on 12/30. 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.
Wed 12/318:54 amMSP - ORD
Nonstop1h 50mSun Country Air
Fri 1/211:51 amORD - MSP
Nonstop1h 39mSun Country Air
Deal found 12/30![Sun Country Air logo]()
$383
This Kiwi.com deal was found by Cheapflights users on 12/30. 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.
Wed 12/318:54 amMSP - ORD
Nonstop1h 50mSun Country Air
Sun 1/47:50 pmORD - MSP
Nonstop1h 39mSun Country Air
Deal found 12/30![Sun Country Air logo]()
$453
This Priceline deal was found by Cheapflights users on 12/30. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/3110:00 amMSP - ORD
1 stop3h 45mMultiple Airlines
Fri 1/212:26 pmORD - MSP
Nonstop1h 36mMultiple Airlines
Deal found 12/30![Multiple Airlines logo]()
$457
This Orbitz deal was found by Cheapflights users on 12/30. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/3110:00 amMSP - ORD
1 stop3h 45mMultiple Airlines
Thu 1/16:14 pmORD - MSP
Nonstop1h 39mMultiple Airlines
Deal found 12/30![Multiple Airlines logo]()
$481
This Kiwi.com deal was found by Cheapflights users on 12/30. 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.
Wed 12/3110:00 amMSP - ORD
1 stop3h 45mMultiple Airlines
Mon 1/127:50 pmORD - MSP
1 stop27h 28mMultiple Airlines
Deal found 12/30![Multiple Airlines logo]()
$487
This Southwest deal was found by Cheapflights users on 12/31. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/317:15 amMSP - MDW
Nonstop1h 45mSouthwest
Wed 1/77:45 pmMDW - MSP
Nonstop1h 30mSouthwest
Deal found 12/31![Southwest logo]()
$594
This Southwest deal was found by Cheapflights users on 12/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/313:25 pmMSP - MDW
Nonstop1h 35mSouthwest
Sat 1/312:40 pmMDW - MSP
Nonstop1h 30mSouthwest
Deal found 12/30![Southwest logo]()
$723
This Delta deal was found by Cheapflights users on 12/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/319:10 amMSP - MDW
Nonstop1h 56mDelta
Thu 1/19:29 amMDW - MSP
1 stop3h 57mDelta
Deal found 12/30![Delta logo]()
$733
This Southwest deal was found by Cheapflights users on 12/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/313:25 pmMSP - MDW
Nonstop1h 35mSouthwest
Fri 1/23:15 pmMDW - MSP
2 stops8h 15mSouthwest
Deal found 12/30![Southwest logo]()
$738
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 January 1, 2026.
Most accurate provider | Mytrip 3 stars |
|---|---|
Most trusted provider | Mytrip 3 stars |
Round-trip from | $143 (Delta) |
One-way from | $59 (Sun Country Air) |
Popular in | February |
Cheapest in | September |
Average price | $221 |
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 January 1, 2026.
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
Sat 1/17
2:30 pm-4:16 pm
Nonstop1h 46m
Chicago Midway
Sun 1/18
9:50 am-11:34 am
Nonstop1h 44m
$143
MinneapolisChicago
MSP - ORD
MSPORD
Minneapolis St Paul
Sat 1/17
4:23 pm-5:54 pm
Nonstop1h 31m
Chicago O'Hare Intl
Tue 1/20
12:30 pm-2:12 pm
Nonstop1h 42m
$163
MinneapolisChicago
MSP - MDW
MSPMDW
Minneapolis St Paul
Sat 1/17
5:35 am-11:45 am
1 stop6h 10m
Chicago Midway
Sun 1/18
8:40 am-10:20 am
Nonstop1h 40m
$188
MinneapolisChicago
MSP - MDW
MSPMDW
Minneapolis St Paul
Tue 2/17
12:00 pm-1:35 pm
Nonstop1h 35m
Chicago Midway
Wed 2/18
8:40 am-10:20 am
Nonstop1h 40m
$192
MinneapolisChicago
MSP - MDW
MSPMDW
Minneapolis St Paul
Sat 2/14
2:30 pm-4:14 pm
Nonstop1h 44m
Chicago Midway
Tue 2/17
9:50 am-11:32 am
Nonstop1h 42m
$192
MinneapolisChicago
MSP - MDW
MSPMDW
Minneapolis St Paul
Wed 2/11
7:05 am-9:08 am
Nonstop2h 03m
Chicago Midway
Sat 2/14
11:45 am-1:30 pm
Nonstop1h 45m
$192
MinneapolisChicago
MSP - MDW
MSPMDW
Minneapolis St Paul
Wed 4/1
4:30 pm-9:55 pm
1 stop5h 25m
Chicago Midway
Sat 4/4
10:10 am-11:40 am
Nonstop1h 30m
$201
MinneapolisChicago
MSP - MDW
MSPMDW
Minneapolis St Paul
Sat 1/17
2:30 pm-4:16 pm
Nonstop1h 46m
Chicago Midway
Wed 1/28
9:33 am-1:45 pm
1 stop4h 12m
$202
MinneapolisChicago
MSP - MDW
MSPMDW
Minneapolis St Paul
Sat 1/17
8:55 am-12:48 pm
1 stop3h 53m
Chicago Midway
Sat 1/17
5:00 pm-6:54 pm
Nonstop1h 54m
$210
MinneapolisChicago
MSP - ORD
MSPORD
Minneapolis St Paul
Sat 1/17
5:16 pm-6:55 pm
Nonstop1h 39m
Chicago O'Hare Intl
Thu 1/22
8:18 pm-9:57 pm
Nonstop1h 39m
$212
Showing 1-10 of 57 results
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 26, 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 January 1, 2026.
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 29% 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 27, 2025.
Travelers seeking maximum savings on their Saint Paul to Chicago flight should consider departing on Saturday afternoons 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.
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 January 1, 2026.
The most flights from SA1 to CHI are scheduled on a Thursday (85 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (5 on average).
How much does it cost to fly round-trip from Saint Paul 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 January 1, 2026.
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.
Overall
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Overall
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Overall
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Overall
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Overall
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Overall
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
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.
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Book flights to Chicago if you plan to visit one of these locationsLansing
Merrillville
Hammond
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Alternative routes for Saint Paul to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
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 January 1, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$39 | Average$98 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$68 | Average$157 | FlexibilityNo cancel fee | On-time83% | |
| Cheapest$69 | Average$320 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$97 | Average$305 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$97 | Average$219 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$103 | Average$221 | FlexibilityNo cancel fee | On-time63% |