$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 5/6. Fares are subject to change and may not be available on all flights or dates of travel.
MSP — CHI
May 1 — May 81
Round-trip
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
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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 December, booked 25 days in advance, depart on a Friday or Thursday and return on a Thursday
Cheap flight deals from Saint Paul to Chicago
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Best
Last-minute
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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 April 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 April 1, 2026.
This Delta deal was found by Cheapflights users on 3/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/287:00 am
MSP
- MDW
Nonstop1h 46m
Delta
Tue 5/57:16 pm
MDW
- MSP
Nonstop1h 44m
Delta
Deal found 3/31![Delta logo]()
$117
This United Airlines deal was found by Cheapflights users on 3/31. 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.
Tue 4/286:00 am
MSP
- ORD
Nonstop1h 37m
United Airlines
Tue 5/512:40 pm
ORD
- MSP
Nonstop1h 38m
United Airlines
Deal found 3/31![United Airlines logo]()
$117
This Southwest deal was found by Cheapflights users on 3/31. 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.
Tue 4/283:15 pm
MSP
- MDW
Nonstop1h 35m
Southwest
Tue 5/54:40 pm
MDW
- MSP
1 stop5h 50m
Southwest
Deal found 3/31![Southwest logo]()
$127
This Kiwi.com deal was found by Cheapflights users on 3/31. 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 4/204:24 pm
MSP
- ORD
Nonstop1h 36m
Sun Country Air
Thu 4/237:13 pm
ORD
- MSP
Nonstop1h 46m
Sun Country Air
Deal found 3/31![Sun Country Air logo]()
$137
This Cheapflightsfares deal was found by Cheapflights users on 3/31. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/85:30 pm
MSP
- ORD
Nonstop1h 36m
Sun Country Air
Mon 5/188:06 pm
ORD
- MSP
Nonstop1h 44m
Sun Country Air
Deal found 3/31![Sun Country Air logo]()
$138
This Expedia deal was found by Cheapflights users on 3/29. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/2011:30 am
MSP
- MDW
1 stop8h 01m
Frontier
Fri 4/246:49 pm
MDW
- MSP
1 stop15h 01m
Frontier
Deal found 3/29![Frontier logo]()
$140
This Orbitz deal was found by Cheapflights users on 3/29. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/411:30 am
MSP
- ORD
1 stop11h 09m
Frontier
Thu 5/79:42 pm
ORD
- MSP
1 stop11h 37m
Frontier
Deal found 3/29![Frontier logo]()
$140
This Southwest deal was found by Cheapflights users on 3/31. 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.
Tue 4/287:10 am
MSP
- ORD
1 stop5h 40m
Southwest
Tue 5/52:40 pm
ORD
- MSP
1 stop8h 25m
Southwest
Deal found 3/31![Southwest logo]()
$142
This lastminute.com deal was found by Cheapflights users on 3/29. 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 lastminute.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/165:18 pm
MSP
- ORD
Nonstop1h 36m
Sun Country Air
Sun 4/197:20 am
ORD
- MSP
Nonstop1h 46m
Sun Country Air
Deal found 3/29![Sun Country Air logo]()
$143
This Delta deal was found by Cheapflights users on 3/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/274:57 pm
MSP
- MDW
Nonstop1h 39m
Delta
Wed 4/299:29 am
MDW
- MSP
Nonstop1h 41m
Delta
Deal found 3/31![Delta logo]()
$147
This Kiwi.com deal was found by Cheapflights users on 3/31. 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.
Fri 7/33:30 pm
MSP
- ORD
Nonstop1h 49m
Sun Country Air
Mon 7/66:19 pm
ORD
- MSP
Nonstop1h 46m
Sun Country Air
Deal found 3/31![Sun Country Air logo]()
$147
This Kiwi.com deal was found by Cheapflights users on 3/30. 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.
Thu 4/165:18 pm
MSP
- ORD
Nonstop1h 36m
Sun Country Air
Mon 4/207:05 pm
ORD
- MSP
Nonstop1h 46m
Sun Country Air
Deal found 3/30![Sun Country Air logo]()
$149
Best flights from Saint Paul to ChicagoDiscover carefully curated flight deals from Saint Paul to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 1, 2026.
Discover carefully curated flight deals from Saint Paul to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 1, 2026.
This Southwest deal was found by Cheapflights users on 3/28. 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.
Mon 5/185:20 am
MSP
- MDW
Nonstop1h 30m
Southwest
Tue 5/1910:45 am
MDW
- MSP
Nonstop1h 35m
Southwest
Deal found 3/28![Southwest logo]()
$177
This United Airlines deal was found by Cheapflights users on 3/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/2310:00 am
MSP
- ORD
Nonstop1h 35m
United Airlines
Sat 4/2512:42 pm
ORD
- MSP
Nonstop1h 44m
United Airlines
Deal found 3/30![United Airlines logo]()
$177
This Delta deal was found by Cheapflights users on 3/27. 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.
Tue 5/197:45 pm
MSP
- ORD
Nonstop1h 35m
Delta
Wed 5/208:05 pm
ORD
- MSP
Nonstop1h 45m
Delta
Deal found 3/27![Delta logo]()
$177
This KAYAK deal was found by Cheapflights users on 3/31. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/1311:29 am
MSP
- ORD
Nonstop1h 45m
American Airlines
Fri 5/159:10 am
ORD
- MSP
Nonstop1h 44m
American Airlines
Deal found 3/31![American Airlines logo]()
$260
This Kiwi.com deal was found by Cheapflights users on 3/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/254:30 pm
MSP
- RFD
1 stop17h 17m
Multiple Airlines
Thu 5/710:37 am
RFD
- MSP
2 stops29h 25m
Multiple Airlines
Deal found 3/29![Multiple Airlines logo]()
$334
This Southwest deal was found by Cheapflights users on 3/27. 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.
Mon 6/85:00 am
MSP
- MDW
Nonstop1h 30m
Southwest
Tue 6/95:20 pm
MDW
- MSP
1 stop6h 35m
Southwest
Deal found 3/27![Southwest logo]()
$187
This Delta deal was found by Cheapflights users on 3/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/44:55 pm
MSP
- ORD
1 stop3h 45m
Delta
Wed 5/66:25 am
ORD
- MSP
Nonstop1h 46m
Delta
Deal found 3/31![Delta logo]()
$192
This Southwest deal was found by Cheapflights users on 3/28. 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 5/64:30 pm
MSP
- MDW
1 stop5h 20m
Southwest
Sat 5/93:30 pm
MDW
- MSP
2 stops7h 05m
Southwest
Deal found 3/28![Southwest logo]()
$202
This Delta deal was found by Cheapflights users on 3/30. 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.
Sat 5/301:20 pm
MSP
- ORD
Nonstop1h 37m
Delta
Wed 6/38:42 am
ORD
- MSP
Nonstop1h 36m
Delta
Deal found 3/30![Delta logo]()
$216
This Southwest deal was found by Cheapflights users on 3/30. 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.
Mon 4/205:20 pm
MSP
- MDW
1 stop5h 25m
Southwest
Sat 4/253:30 pm
MDW
- MSP
2 stops7h 05m
Southwest
Deal found 3/30![Southwest logo]()
$202
This Delta deal was found by Cheapflights users on 3/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/2212:45 pm
MSP
- ORD
1 stop6h 07m
Delta
Thu 4/238:50 am
ORD
- MSP
Nonstop1h 40m
Delta
Deal found 3/31![Delta logo]()
$222
This Southwest deal was found by Cheapflights users on 3/30. 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.
Mon 4/206:15 am
MSP
- ORD
1 stop6h 35m
Southwest
Sat 4/251:55 pm
ORD
- MSP
1 stop8h 40m
Southwest
Deal found 3/30![Southwest logo]()
$202
This Delta deal was found by Cheapflights users on 3/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/207:45 pm
MSP
- ORD
Nonstop1h 35m
Delta
Fri 5/292:00 pm
ORD
- MSP
1 stop6h 44m
Delta
Deal found 3/31![Delta logo]()
$226
This Southwest deal was found by Cheapflights users on 3/31. 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 4/296:55 am
MSP
- ORD
1 stop8h 05m
Southwest
Wed 5/62:40 pm
ORD
- MSP
1 stop8h 25m
Southwest
Deal found 3/31![Southwest logo]()
$208
This Delta deal was found by Cheapflights users on 3/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/203:15 pm
MSP
- ORD
Nonstop1h 36m
Delta
Sat 5/301:44 pm
ORD
- MSP
1 stop6h 54m
Delta
Deal found 3/31![Delta logo]()
$226
This Kiwi.com deal was found by Cheapflights users on 3/27. 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 4/114:30 pm
MSP
- RFD
1 stop17h 17m
Multiple Airlines
Wed 4/1512:09 pm
RFD
- MSP
1 stop27h 03m
Multiple Airlines
Deal found 3/27![Multiple Airlines logo]()
$382
This Delta deal was found by Cheapflights users on 3/27. 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.
Tue 5/1911:40 am
MSP
- MDW
Nonstop1h 39m
Delta
Thu 5/219:23 am
MDW
- MSP
Nonstop1h 37m
Delta
Deal found 3/27![Delta logo]()
$246
This Southwest deal was found by Cheapflights users on 3/27. 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.
Mon 4/202:25 pm
MSP
- MDW
Nonstop1h 25m
Southwest
Wed 4/224:40 pm
MDW
- MSP
1 stop5h 50m
Southwest
Deal found 3/27![Southwest logo]()
$257
This Kiwi.com deal was found by Cheapflights users on 3/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/254:30 pm
MSP
- RFD
1 stop17h 17m
Multiple Airlines
Sun 5/310:37 am
RFD
- MSP
2 stops23h 58m
Multiple Airlines
Deal found 3/29![Multiple Airlines logo]()
$391
This Delta deal was found by Cheapflights users on 3/27. 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 6/1010:00 am
MSP
- ORD
Nonstop1h 31m
Delta
Fri 6/125:57 pm
ORD
- MSP
Nonstop1h 41m
Delta
Deal found 3/27![Delta logo]()
$246
This Southwest deal was found by Cheapflights users on 3/30. 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.
Mon 5/44:55 pm
MSP
- MDW
1 stop6h 35m
Southwest
Wed 5/64:40 pm
MDW
- MSP
1 stop5h 50m
Southwest
Deal found 3/30![Southwest logo]()
$267
This Kiwi.com deal was found by Cheapflights users on 3/28. 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 5/222:00 pm
MSP
- RFD
1 stop19h 21m
Multiple Airlines
Sun 5/249:21 am
RFD
- MSP
1 stop6h 55m
Multiple Airlines
Deal found 3/28![Multiple Airlines logo]()
$403
This KAYAK deal was found by Cheapflights users on 3/31. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/137:00 am
MSP
- MDW
Nonstop1h 42m
Delta
Fri 5/159:23 am
MDW
- MSP
Nonstop1h 37m
Delta
Deal found 3/31![Delta logo]()
$261
This Southwest deal was found by Cheapflights users on 3/27. 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 4/227:10 am
MSP
- MDW
2 stops8h 35m
Southwest
Thu 4/238:00 am
MDW
- MSP
2 stops8h 35m
Southwest
Deal found 3/27![Southwest logo]()
$289
This Kiwi.com deal was found by Cheapflights users on 3/28. 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 6/54:57 pm
MSP
- RFD
2 stops16h 20m
Multiple Airlines
Sun 6/79:19 am
RFD
- MSP
1 stop9h 43m
Multiple Airlines
Deal found 3/28![Multiple Airlines logo]()
$435
This Delta deal was found by Cheapflights users on 3/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/2811:30 am
MSP
- MDW
Nonstop1h 39m
Delta
Wed 7/19:54 am
MDW
- MSP
Nonstop1h 41m
Delta
Deal found 3/29![Delta logo]()
$295
This Kiwi.com deal was found by Cheapflights users on 3/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/254:30 pm
MSP
- RFD
1 stop17h 17m
Multiple Airlines
Wed 5/612:09 pm
RFD
- MSP
2 stops33h 44m
Multiple Airlines
Deal found 3/29![Multiple Airlines logo]()
$435
This Southwest deal was found by Cheapflights users on 3/31. 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 5/137:50 am
MSP
- MDW
1 stop3h 45m
Southwest
Fri 5/155:40 pm
MDW
- MSP
1 stop5h 40m
Southwest
Deal found 3/31![Southwest logo]()
$306
This Kiwi.com deal was found by Cheapflights users on 3/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/2912:00 pm
MSP
- RFD
1 stop24h 00m
Multiple Airlines
Thu 5/712:50 pm
RFD
- MSP
1 stop11h 02m
Multiple Airlines
Deal found 3/29![Multiple Airlines logo]()
$479
This Kiwi.com deal was found by Cheapflights users on 3/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/277:24 am
MSP
- RFD
1 stop10h 55m
Multiple Airlines
Sun 5/310:37 am
RFD
- MSP
1 stop28h 26m
Multiple Airlines
Deal found 3/29![Multiple Airlines logo]()
$493
Last-minute flights from Saint Paul to ChicagoDiscover last-minute flight deals from Saint Paul to Chicago. Data last updated April 1, 2026 and is based on user searches.
Discover last-minute flight deals from Saint Paul to Chicago. Data last updated April 1, 2026 and is based on user searches.
This lastminute.com deal was found by Cheapflights users on 3/29. 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 lastminute.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/165:18 pm
MSP
- ORD
Nonstop1h 36m
Sun Country Air
Sun 4/197:20 am
ORD
- MSP
Nonstop1h 46m
Sun Country Air
Deal found 3/29![Sun Country Air logo]()
$143
This Kiwi.com deal was found by Cheapflights users on 3/27. 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 4/165:18 pm
MSP
- ORD
Nonstop1h 36m
Sun Country Air
Thu 4/237:13 pm
ORD
- MSP
Nonstop1h 46m
Sun Country Air
Deal found 3/27![Sun Country Air logo]()
$147
This Kiwi.com deal was found by Cheapflights users on 3/30. 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.
Thu 4/165:18 pm
MSP
- ORD
Nonstop1h 36m
Sun Country Air
Mon 4/207:05 pm
ORD
- MSP
Nonstop1h 46m
Sun Country Air
Deal found 3/30![Sun Country Air logo]()
$149
This Kiwi.com deal was found by Cheapflights users on 3/31. 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 4/204:24 pm
MSP
- ORD
Nonstop1h 36m
Sun Country Air
Thu 4/237:13 pm
ORD
- MSP
Nonstop1h 46m
Sun Country Air
Deal found 3/31![Sun Country Air logo]()
$137
This Super.com deal was found by Cheapflights users on 3/29. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/204:24 pm
MSP
- ORD
Nonstop1h 36m
Sun Country Air
Fri 4/247:35 pm
ORD
- MSP
Nonstop1h 46m
Sun Country Air
Deal found 3/29![Sun Country Air logo]()
$138
This Expedia deal was found by Cheapflights users on 3/29. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/2011:30 am
MSP
- MDW
1 stop8h 01m
Frontier
Fri 4/246:49 pm
MDW
- MSP
1 stop15h 01m
Frontier
Deal found 3/29![Frontier logo]()
$140
This Delta deal was found by Cheapflights users on 3/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/274:57 pm
MSP
- MDW
Nonstop1h 39m
Delta
Wed 4/299:29 am
MDW
- MSP
Nonstop1h 41m
Delta
Deal found 3/31![Delta logo]()
$147
This Delta deal was found by Cheapflights users on 3/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/287:00 am
MSP
- MDW
Nonstop1h 46m
Delta
Tue 5/57:16 pm
MDW
- MSP
Nonstop1h 44m
Delta
Deal found 3/31![Delta logo]()
$117
This United Airlines deal was found by Cheapflights users on 3/31. 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.
Tue 4/286:00 am
MSP
- ORD
Nonstop1h 37m
United Airlines
Tue 5/512:40 pm
ORD
- MSP
Nonstop1h 38m
United Airlines
Deal found 3/31![United Airlines logo]()
$117
This Southwest deal was found by Cheapflights users on 3/31. 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.
Tue 4/283:15 pm
MSP
- MDW
Nonstop1h 35m
Southwest
Tue 5/54:40 pm
MDW
- MSP
1 stop5h 50m
Southwest
Deal found 3/31![Southwest logo]()
$127
This Southwest deal was found by Cheapflights users on 3/31. 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.
Tue 4/287:10 am
MSP
- ORD
1 stop5h 40m
Southwest
Tue 5/52:40 pm
ORD
- MSP
1 stop8h 25m
Southwest
Deal found 3/31![Southwest logo]()
$142
This Orbitz deal was found by Cheapflights users on 3/27. 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.
Thu 4/305:30 pm
MSP
- ORD
Nonstop1h 36m
Multiple Airlines
Tue 5/59:42 pm
ORD
- MSP
1 stop11h 37m
Multiple Airlines
Deal found 3/27![Multiple Airlines logo]()
$150
One-way flights from Saint Paul to ChicagoSearch for one-way flight options from Saint Paul to Chicago. Find affordable one-way fares based on user searches. Data last updated April 1, 2026.
Search for one-way flight options from Saint Paul to Chicago. Find affordable one-way fares based on user searches. Data last updated April 1, 2026.
This Delta deal was found by Cheapflights users on 3/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/64:57 pm
MSP
- MDW
Nonstop1h 39m
Delta
Deal found 3/31![Delta logo]()
$59
This United Airlines deal was found by Cheapflights users on 3/31. 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 5/69:57 am
MSP
- ORD
Nonstop1h 36m
United Airlines
Deal found 3/31![United Airlines logo]()
$59
This Kiwi.com deal was found by Cheapflights users on 3/31. 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 9/289:10 am
MSP
- ORD
Nonstop1h 38m
Sun Country Air
Deal found 3/31![Sun Country Air logo]()
$68
This Super.com deal was found by Cheapflights users on 3/29. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/2410:34 am
MSP
- MDW
1 stop7h 20m
Frontier
Deal found 3/29![Frontier logo]()
$69
This Cheapflightsfares deal was found by Cheapflights users on 3/31. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/313:30 pm
MSP
- ORD
Nonstop1h 42m
Sun Country Air
Deal found 3/31![Sun Country Air logo]()
$69
This Kiwi.com deal was found by Cheapflights users on 3/31. 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 4/234:42 pm
MSP
- ORD
Nonstop1h 36m
Sun Country Air
Deal found 3/31![Sun Country Air logo]()
$71
This Southwest deal was found by Cheapflights users on 3/31. 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 4/227:10 am
MSP
- MDW
2 stops8h 35m
Southwest
Deal found 3/31![Southwest logo]()
$74
This Super.com deal was found by Cheapflights users on 3/27. 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 4/1710:34 am
MSP
- MDW
1 stop29h 26m
Frontier
Deal found 3/27![Frontier logo]()
$75
This Super.com deal was found by Cheapflights users on 3/30. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/2311:30 am
MSP
- ORD
1 stop11h 09m
Frontier
Deal found 3/30![Frontier logo]()
$75
This Frontier deal was found by Cheapflights users on 3/29. 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.
Fri 5/112:36 pm
MSP
- MDW
1 stop9h 50m
Frontier
Deal found 3/29![Frontier logo]()
$76
This Frontier deal was found by Cheapflights users on 3/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/2011:47 am
MSP
- ORD
1 stop13h 12m
Frontier
Deal found 3/30![Frontier logo]()
$76
This Trip.com deal was found by Cheapflights users on 3/28. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/2711:47 am
MSP
- ORD
1 stop13h 05m
Frontier
Deal found 3/28![Frontier logo]()
$77
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 April 1, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $117 (Delta) |
One-way from | $59 (Delta) |
Popular in | March |
Cheapest in | September |
Average price | $169 |
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 April 1, 2026.
Use the filters below to find and compare flights from Saint Paul to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
MinneapolisChicago
MSP - MDW
MSPMDW
Minneapolis St Paul
Mon 5/18
5:20 am-6:50 am
Nonstop1h 30m
Chicago Midway
Tue 5/19
10:45 am-12:20 pm
Nonstop1h 35m
$177
MinneapolisChicago
MSP - ORD
MSPORD
Minneapolis St Paul
Thu 4/23
10:00 am-11:35 am
Nonstop1h 35m
Chicago O'Hare Intl
Sat 4/25
12:42 pm-2:26 pm
Nonstop1h 44m
$177
MinneapolisChicago
MSP - ORD
MSPORD
Minneapolis St Paul
Tue 5/19
7:45 pm-9:20 pm
Nonstop1h 35m
Chicago O'Hare Intl
Wed 5/20
8:05 pm-9:50 pm
Nonstop1h 45m
$177
MinneapolisChicago
MSP - MDW
MSPMDW
Minneapolis St Paul
Mon 6/8
5:00 am-6:30 am
Nonstop1h 30m
Chicago Midway
Tue 6/9
5:20 pm-11:55 pm
1 stop6h 35m
$187
MinneapolisChicago
MSP - ORD
MSPORD
Minneapolis St Paul
Mon 5/4
4:55 pm-8:40 pm
1 stop3h 45m
Chicago O'Hare Intl
Wed 5/6
6:25 am-8:11 am
Nonstop1h 46m
$192
MinneapolisChicago
MSP - MDW
MSPMDW
Minneapolis St Paul
Wed 5/6
4:30 pm-9:50 pm
1 stop5h 20m
Chicago Midway
Sat 5/9
3:30 pm-10:35 pm
2 stops7h 05m
$202
MinneapolisChicago
MSP - MDW
MSPMDW
Minneapolis St Paul
Mon 4/20
5:20 pm-10:45 pm
1 stop5h 25m
Chicago Midway
Sat 4/25
3:30 pm-10:35 pm
2 stops7h 05m
$202
MinneapolisChicago
MSP - ORD
MSPORD
Minneapolis St Paul
Mon 4/20
6:15 am-12:50 pm
1 stop6h 35m
Chicago O'Hare Intl
Sat 4/25
1:55 pm-10:35 pm
1 stop8h 40m
$202
MinneapolisChicago
MSP - ORD
MSPORD
Minneapolis St Paul
Wed 4/29
6:55 am-3:00 pm
1 stop8h 05m
Chicago O'Hare Intl
Wed 5/6
2:40 pm-11:05 pm
1 stop8h 25m
$208
MinneapolisChicago
MSP - ORD
MSPORD
Minneapolis St Paul
Sat 5/30
1:20 pm-2:57 pm
Nonstop1h 37m
Chicago O'Hare Intl
Wed 6/3
8:42 am-10:18 am
Nonstop1h 36m
$216
Showing 1-10 of 60 resultsSorted by cheapest first
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.
MSP-MDW
MSP-ORD
MSP-RFD
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
SA1-CHI
MSP-MDW
MSP-ORD
MSP-RFD
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 March 13, 2026.
Booking 25 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 February 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 April 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 30% 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 March 28, 2026.
Travelers seeking maximum savings on their Saint Paul to Chicago flight should consider departing on Thursday afternoons when fares are most often at their lowest. Sunday afternoons 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 April 1, 2026.
The most flights from SA1 to CHI are scheduled on a Tuesday (108 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (17 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 April 1, 2026.
Read through reviews of airlines operating flights from Saint Paul to Chicago, such as Southwest,Delta, andUnited Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Food
7.0
Entertainment
7.5
Crew
8.6
Overall
8.0
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Food
7.0
Entertainment
7.5
Crew
8.6
Overall
8.0
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Food
7.0
Entertainment
7.5
Crew
8.6
Overall
8.0
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Food
7.0
Entertainment
7.5
Crew
8.6
Overall
8.0
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Food
7.0
Entertainment
7.5
Crew
8.6
Overall
8.0
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Food
7.0
Entertainment
7.5
Crew
8.6
Overall
8.0
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
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.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsLansing
Merrillville
Hammond
Porter
Benton Harbor
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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.
Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on April 1, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
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Find flights from Saint Paul to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Saint Paul and Chicago flights
Browse other Saint Paul and Chicago flight options. Last updated on April 1, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
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 April 1, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$38 | Average$96 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$53 | Average$228 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$59 | Average$149 | FlexibilityNo cancel fee | On-time83% | |
| Cheapest$91 | Average$318 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$93 | Average$235 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$100 | Average$223 | FlexibilityNo cancel fee | On-time63% |