$68+ 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 7/22. Fares are subject to change and may not be available on all flights or dates of travel.
MSP — CHI
Jul 30 — Aug 61
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 December or September, 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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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 June 30, 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 June 30, 2026.
This Southwest deal was found by Cheapflights users on 6/30. 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.
Tue 7/287:05 am
MSP
- MDW
1 stop7h 25m
Southwest
Tue 8/48:30 pm
MDW
- MSP
Nonstop1h 30m
Southwest
Deal found 6/30![Southwest logo]()
$127
This United Airlines deal was found by Cheapflights users on 6/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/16:00 am
MSP
- ORD
Nonstop1h 44m
United Airlines
Sat 8/87:57 pm
ORD
- MSP
Nonstop1h 44m
United Airlines
Deal found 6/28![United Airlines logo]()
$129
This Southwest deal was found by Cheapflights users on 6/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/56:15 am
MSP
- MDW
Nonstop1h 25m
Southwest
Sat 8/86:35 am
MDW
- MSP
1 stop9h 35m
Southwest
Deal found 6/29![Southwest logo]()
$133
This Southwest deal was found by Cheapflights users on 6/30. 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.
Tue 8/48:00 am
MSP
- MDW
1 stop5h 55m
Southwest
Tue 8/44:40 pm
MDW
- MSP
1 stop5h 45m
Southwest
Deal found 6/30![Southwest logo]()
$137
This Super.com deal was found by Cheapflights users on 6/28. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/219:05 am
MSP
- ORD
Nonstop1h 49m
Sun Country Air
Thu 8/69:00 pm
ORD
- MSP
Nonstop1h 43m
Sun Country Air
Deal found 6/28![Sun Country Air logo]()
$137
This Southwest deal was found by Cheapflights users on 6/27. 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.
Sat 8/85:30 am
MSP
- MDW
Nonstop1h 25m
Southwest
Sat 8/227:55 am
MDW
- MSP
2 stops12h 10m
Southwest
Deal found 6/27![Southwest logo]()
$138
This Sun Country Air deal was found by Cheapflights users on 6/27. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/219:05 am
MSP
- ORD
Nonstop1h 49m
Sun Country Air
Thu 7/237:25 am
ORD
- MSP
Nonstop1h 46m
Sun Country Air
Deal found 6/27![Sun Country Air logo]()
$138
This Delta deal was found by Cheapflights users on 6/29. 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.
Sat 11/710:10 am
MSP
- MDW
Nonstop1h 38m
Delta
Thu 11/265:35 pm
MDW
- MSP
Nonstop1h 40m
Delta
Deal found 6/29![Delta logo]()
$141
This Delta deal was found by Cheapflights users on 6/29. 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.
Sat 8/84:00 pm
MSP
- ORD
Nonstop1h 41m
Delta
Mon 8/108:28 am
ORD
- MSP
Nonstop1h 35m
Delta
Deal found 6/29![Delta logo]()
$141
This American Airlines deal was found by Cheapflights users on 6/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/88:10 am
MSP
- ORD
Nonstop1h 50m
American Airlines
Mon 8/1010:40 pm
ORD
- MSP
Nonstop1h 44m
American Airlines
Deal found 6/28![American Airlines logo]()
$142
This Delta deal was found by Cheapflights users on 6/25. 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 7/216:55 am
MSP
- MDW
Nonstop1h 42m
Delta
Tue 7/281:49 pm
MDW
- MSP
Nonstop1h 44m
Delta
Deal found 6/25![Delta logo]()
$147
This Delta deal was found by Cheapflights users on 6/30. 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 7/227:00 am
MSP
- ORD
Nonstop1h 30m
Delta
Sat 7/258:27 am
ORD
- MSP
Nonstop1h 35m
Delta
Deal found 6/30![Delta logo]()
$147
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 June 30, 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 June 30, 2026.
This Southwest deal was found by Cheapflights users on 6/30. 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 8/1210:35 am
MSP
- MDW
Nonstop1h 25m
Southwest
Wed 8/125:20 pm
MDW
- MSP
1 stop5h 30m
Southwest
Deal found 6/30![Southwest logo]()
$127
This Delta deal was found by Cheapflights users on 6/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/119:00 am
MSP
- ORD
1 stop4h 08m
Delta
Wed 8/128:28 am
ORD
- MSP
Nonstop1h 35m
Delta
Deal found 6/28![Delta logo]()
$177
This Sun Country Air deal was found by Cheapflights users on 6/26. 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 8/73:35 pm
MSP
- ORD
Nonstop1h 49m
Sun Country Air
Mon 8/106:39 pm
ORD
- MSP
Nonstop1h 46m
Sun Country Air
Deal found 6/26![Sun Country Air logo]()
$199
This United Airlines deal was found by Cheapflights users on 6/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/511:32 am
MSP
- ORD
Nonstop1h 43m
United Airlines
Sun 8/98:50 am
ORD
- MSP
Nonstop1h 46m
United Airlines
Deal found 6/29![United Airlines logo]()
$216
This Southwest deal was found by Cheapflights users on 6/25. 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.
Sat 8/85:30 am
MSP
- MDW
Nonstop1h 25m
Southwest
Mon 8/108:00 am
MDW
- MSP
Nonstop1h 45m
Southwest
Deal found 6/25![Southwest logo]()
$142
This Kiwi.com deal was found by Cheapflights users on 6/28. 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.
Wed 7/82:40 pm
MSP
- RFD
1 stop17h 49m
Multiple Airlines
Sun 7/129:19 am
RFD
- MSP
1 stop12h 36m
Multiple Airlines
Deal found 6/28![Multiple Airlines logo]()
$346
This Delta deal was found by Cheapflights users on 6/29. 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.
Wed 8/126:04 am
MSP
- ORD
1 stop7h 04m
Delta
Sat 8/153:00 pm
ORD
- MSP
Nonstop1h 40m
Delta
Deal found 6/29![Delta logo]()
$181
This Southwest deal was found by Cheapflights users on 6/30. 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.
Thu 8/67:55 am
MSP
- MDW
1 stop4h 20m
Southwest
Sat 8/86:35 am
MDW
- MSP
1 stop9h 35m
Southwest
Deal found 6/30![Southwest logo]()
$174
This Delta deal was found by Cheapflights users on 6/26. 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 8/256:04 am
MSP
- ORD
1 stop4h 38m
Delta
Sat 8/296:00 am
ORD
- MSP
Nonstop1h 30m
Delta
Deal found 6/26![Delta logo]()
$189
This Delta deal was found by Cheapflights users on 6/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/184:40 pm
MSP
- MDW
Nonstop1h 39m
Delta
Sat 9/192:00 pm
MDW
- MSP
Nonstop1h 40m
Delta
Deal found 6/28![Delta logo]()
$216
This Delta deal was found by Cheapflights users on 6/26. 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.
Fri 9/46:57 am
MSP
- MDW
Nonstop1h 42m
Delta
Sat 9/54:52 pm
MDW
- MSP
Nonstop1h 44m
Delta
Deal found 6/26![Delta logo]()
$216
This Southwest deal was found by Cheapflights users on 6/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/277:35 am
MSP
- MDW
2 stops6h 15m
Southwest
Tue 9/295:20 pm
MDW
- MSP
1 stop5h 30m
Southwest
Deal found 6/29![Southwest logo]()
$241
This Delta deal was found by Cheapflights users on 6/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/198:10 pm
MSP
- ORD
Nonstop1h 37m
Delta
Fri 8/218:28 am
ORD
- MSP
Nonstop1h 35m
Delta
Deal found 6/28![Delta logo]()
$216
This Southwest deal was found by Cheapflights users on 6/26. 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.
Sat 8/15:25 am
MSP
- MDW
Nonstop1h 30m
Southwest
Mon 8/35:05 pm
MDW
- MSP
Nonstop1h 30m
Southwest
Deal found 6/26![Southwest logo]()
$246
This Delta deal was found by Cheapflights users on 6/25. 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.
Fri 8/145:45 pm
MSP
- ORD
Nonstop1h 45m
Delta
Sat 8/153:00 pm
ORD
- MSP
Nonstop1h 40m
Delta
Deal found 6/25![Delta logo]()
$216
This Delta deal was found by Cheapflights users on 6/26. 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 7/267:00 am
MSP
- ORD
Nonstop1h 30m
Delta
Sat 8/16:30 am
ORD
- MSP
Nonstop1h 34m
Delta
Deal found 6/26![Delta logo]()
$216
This Southwest deal was found by Cheapflights users on 6/28. 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.
Sun 7/195:20 am
MSP
- MDW
Nonstop1h 30m
Southwest
Thu 8/133:20 pm
MDW
- MSP
1 stop6h 00m
Southwest
Deal found 6/28![Southwest logo]()
$271
This Kiwi.com deal was found by Cheapflights users on 6/28. 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.
Wed 7/222:35 pm
MSP
- RFD
1 stop17h 54m
Multiple Airlines
Sun 7/269:19 am
RFD
- MSP
1 stop10h 28m
Multiple Airlines
Deal found 6/28![Multiple Airlines logo]()
$408
This Delta deal was found by Cheapflights users on 6/27. 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 8/118:10 pm
MSP
- ORD
Nonstop1h 37m
Delta
Sun 8/166:00 am
ORD
- MSP
Nonstop1h 30m
Delta
Deal found 6/27![Delta logo]()
$216
This Kiwi.com deal was found by Cheapflights users on 6/29. 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 7/152:40 pm
MSP
- RFD
1 stop17h 49m
Multiple Airlines
Sun 7/199:19 am
RFD
- MSP
1 stop13h 28m
Multiple Airlines
Deal found 6/29![Multiple Airlines logo]()
$426
This Southwest deal was found by Cheapflights users on 6/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/59:05 am
MSP
- MDW
2 stops6h 55m
Southwest
Sun 8/96:10 am
MDW
- MSP
1 stop8h 50m
Southwest
Deal found 6/29![Southwest logo]()
$323
This Delta deal was found by Cheapflights users on 6/29. 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.
Mon 8/243:20 pm
MSP
- ORD
Nonstop1h 39m
Delta
Fri 8/281:59 pm
ORD
- MSP
1 stop6h 47m
Delta
Deal found 6/29![Delta logo]()
$250
This Kiwi.com deal was found by Cheapflights users on 6/30. 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.
Fri 7/245:09 pm
MSP
- RFD
2 stops18h 59m
Multiple Airlines
Sun 7/269:19 am
RFD
- MSP
1 stop10h 28m
Multiple Airlines
Deal found 6/30![Multiple Airlines logo]()
$477
This Southwest deal was found by Cheapflights users on 6/30. 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 8/179:15 am
MSP
- MDW
2 stops7h 50m
Southwest
Tue 8/184:40 pm
MDW
- MSP
1 stop5h 45m
Southwest
Deal found 6/30![Southwest logo]()
$327
This Delta deal was found by Cheapflights users on 6/26. 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.
Fri 8/76:04 am
MSP
- ORD
1 stop7h 04m
Delta
Mon 8/108:28 am
ORD
- MSP
Nonstop1h 35m
Delta
Deal found 6/26![Delta logo]()
$258
This Kiwi.com deal was found by Cheapflights users on 6/25. 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 7/178:00 am
MSP
- RFD
1 stop12h 23m
Multiple Airlines
Sun 7/199:19 am
RFD
- MSP
1 stop13h 28m
Multiple Airlines
Deal found 6/25![Multiple Airlines logo]()
$479
This Kiwi.com deal was found by Cheapflights users on 6/30. 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.
Fri 7/104:00 pm
MSP
- RFD
2 stops16h 15m
Multiple Airlines
Sun 7/129:19 am
RFD
- MSP
1 stop12h 36m
Multiple Airlines
Deal found 6/30![Multiple Airlines logo]()
$495
This Delta deal was found by Cheapflights users on 6/29. 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.
Wed 8/266:57 am
MSP
- MDW
Nonstop1h 42m
Delta
Fri 8/287:25 pm
MDW
- MSP
Nonstop1h 45m
Delta
Deal found 6/29![Delta logo]()
$295
This Kiwi.com deal was found by Cheapflights users on 6/26. 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 7/34:59 pm
MSP
- RFD
2 stops19h 14m
Multiple Airlines
Sun 7/59:19 am
RFD
- MSP
1 stop10h 24m
Multiple Airlines
Deal found 6/26![Multiple Airlines logo]()
$791
Last-minute flights from Saint Paul to ChicagoDiscover last-minute flight deals from Saint Paul to Chicago. Data last updated June 30, 2026 and is based on user searches.
Discover last-minute flight deals from Saint Paul to Chicago. Data last updated June 30, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 6/28. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/153:50 pm
MSP
- ORD
Nonstop1h 49m
Sun Country Air
Wed 7/2212:24 pm
ORD
- MSP
Nonstop1h 46m
Sun Country Air
Deal found 6/28![Sun Country Air logo]()
$168
This Super.com deal was found by Cheapflights users on 6/30. 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.
Sat 7/184:15 pm
MSP
- ORD
Nonstop1h 49m
Sun Country Air
Tue 7/2111:55 am
ORD
- MSP
Nonstop1h 46m
Sun Country Air
Deal found 6/30![Sun Country Air logo]()
$157
This Southwest deal was found by Cheapflights users on 6/27. 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.
Tue 7/213:10 pm
MSP
- MDW
1 stop6h 00m
Southwest
Wed 7/225:20 pm
MDW
- MSP
1 stop6h 35m
Southwest
Deal found 6/27![Southwest logo]()
$137
This Super.com deal was found by Cheapflights users on 6/28. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/219:05 am
MSP
- ORD
Nonstop1h 49m
Sun Country Air
Thu 8/69:00 pm
ORD
- MSP
Nonstop1h 43m
Sun Country Air
Deal found 6/28![Sun Country Air logo]()
$137
This Sun Country Air deal was found by Cheapflights users on 6/27. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/219:05 am
MSP
- ORD
Nonstop1h 49m
Sun Country Air
Thu 7/237:25 am
ORD
- MSP
Nonstop1h 46m
Sun Country Air
Deal found 6/27![Sun Country Air logo]()
$138
This Delta deal was found by Cheapflights users on 6/25. 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 7/216:55 am
MSP
- MDW
Nonstop1h 42m
Delta
Tue 7/281:49 pm
MDW
- MSP
Nonstop1h 44m
Delta
Deal found 6/25![Delta logo]()
$147
This Delta deal was found by Cheapflights users on 6/30. 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 7/227:00 am
MSP
- ORD
Nonstop1h 30m
Delta
Sat 7/258:27 am
ORD
- MSP
Nonstop1h 35m
Delta
Deal found 6/30![Delta logo]()
$147
This Sun Country Air deal was found by Cheapflights users on 6/27. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/229:35 am
MSP
- ORD
Nonstop1h 49m
Sun Country Air
Thu 7/237:25 am
ORD
- MSP
Nonstop1h 46m
Sun Country Air
Deal found 6/27![Sun Country Air logo]()
$148
This Kiwi.com deal was found by Cheapflights users on 6/28. 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.
Wed 7/229:35 am
MSP
- ORD
Nonstop1h 49m
Sun Country Air
Sun 7/267:30 am
ORD
- MSP
Nonstop1h 46m
Sun Country Air
Deal found 6/28![Sun Country Air logo]()
$167
This Southwest deal was found by Cheapflights users on 6/30. 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.
Tue 7/287:05 am
MSP
- MDW
1 stop7h 25m
Southwest
Tue 8/48:30 pm
MDW
- MSP
Nonstop1h 30m
Southwest
Deal found 6/30![Southwest logo]()
$127
This Delta deal was found by Cheapflights users on 6/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/288:15 pm
MSP
- ORD
Nonstop1h 37m
Delta
Tue 8/412:29 pm
ORD
- MSP
Nonstop1h 43m
Delta
Deal found 6/28![Delta logo]()
$141
This Delta deal was found by Cheapflights users on 6/29. 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.
Tue 7/284:40 pm
MSP
- MDW
Nonstop1h 38m
Delta
Tue 8/49:59 am
MDW
- MSP
Nonstop1h 43m
Delta
Deal found 6/29![Delta logo]()
$167
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 June 30, 2026.
Search for one-way flight options from Saint Paul to Chicago. Find affordable one-way fares based on user searches. Data last updated June 30, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/28. 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.
Wed 7/229:35 am
MSP
- ORD
Nonstop1h 49m
Sun Country Air
Deal found 6/28![Sun Country Air logo]()
$68
This Southwest deal was found by Cheapflights users on 6/30. 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.
Tue 8/48:00 am
MSP
- MDW
1 stop5h 55m
Southwest
Deal found 6/30![Southwest logo]()
$69
This Sun Country Air deal was found by Cheapflights users on 6/26. 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 9/219:10 am
MSP
- ORD
Nonstop1h 38m
Sun Country Air
Deal found 6/26![Sun Country Air logo]()
$69
This Southwest deal was found by Cheapflights users on 6/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/296:00 am
MSP
- MDW
2 stops7h 20m
Southwest
Deal found 6/29![Southwest logo]()
$74
This Kiwi.com deal was found by Cheapflights users on 6/27. 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 7/184:15 pm
MSP
- ORD
Nonstop1h 49m
Sun Country Air
Deal found 6/27![Sun Country Air logo]()
$78
This Sun Country Air deal was found by Cheapflights users on 6/26. 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 9/174:30 pm
MSP
- ORD
Nonstop1h 38m
Sun Country Air
Deal found 6/26![Sun Country Air logo]()
$79
This American Airlines deal was found by Cheapflights users on 6/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/67:02 am
MSP
- ORD
Nonstop1h 52m
American Airlines
Deal found 6/29![American Airlines logo]()
$82
This Southwest deal was found by Cheapflights users on 6/28. 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 8/315:45 am
MSP
- MDW
Nonstop1h 25m
Southwest
Deal found 6/28![Southwest logo]()
$83
This United Airlines deal was found by Cheapflights users on 6/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/171:16 pm
MSP
- ORD
Nonstop1h 44m
United Airlines
Deal found 6/29![United Airlines logo]()
$83
This KAYAK deal was found by Cheapflights users on 6/30. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/158:00 pm
MSP
- ORD
Nonstop1h 33m
Delta
Deal found 6/30![Delta logo]()
$86
This Delta deal was found by Cheapflights users on 6/26. 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 7/216:55 am
MSP
- MDW
Nonstop1h 42m
Delta
Deal found 6/26![Delta logo]()
$89
This Southwest deal was found by Cheapflights users on 6/30. 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 8/106:20 pm
MSP
- MDW
Nonstop1h 30m
Southwest
Deal found 6/30![Southwest logo]()
$91
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 June 30, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $127 (Southwest) |
One-way from | $68 (Kiwi.com) |
Popular in | March |
Cheapest in | December |
Average price | $294 |
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 June 30, 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
MinneapolisChicago
MSP - MDW
MSPMDW
Minneapolis St Paul
Wed 8/12
10:35 am-12:00 pm
Nonstop1h 25m
Chicago Midway
Wed 8/12
5:20 pm-10:50 pm
1 stop5h 30m
$127
MinneapolisChicago
MSP - MDW
MSPMDW
Minneapolis St Paul
Sat 8/8
5:30 am-6:55 am
Nonstop1h 25m
Chicago Midway
Mon 8/10
8:00 am-9:45 am
Nonstop1h 45m
$142
MinneapolisChicago
MSP - MDW
MSPMDW
Minneapolis St Paul
Thu 8/6
7:55 am-12:15 pm
1 stop4h 20m
Chicago Midway
Sat 8/8
6:35 am-4:10 pm
1 stop9h 35m
$174
MinneapolisChicago
MSP - ORD
MSPORD
Minneapolis St Paul
Tue 8/11
9:00 am-1:08 pm
1 stop4h 08m
Chicago O'Hare Intl
Wed 8/12
8:28 am-10:03 am
Nonstop1h 35m
$177
MinneapolisChicago
MSP - ORD
MSPORD
Minneapolis St Paul
Wed 8/12
6:04 am-1:08 pm
1 stop7h 04m
Chicago O'Hare Intl
Sat 8/15
3:00 pm-4:40 pm
Nonstop1h 40m
$181
MinneapolisChicago
MSP - ORD
MSPORD
Minneapolis St Paul
Tue 8/25
6:04 am-10:42 am
1 stop4h 38m
Chicago O'Hare Intl
Sat 8/29
6:00 am-7:30 am
Nonstop1h 30m
$189
MinneapolisChicago
MSP - ORD
MSPORD
Minneapolis St Paul
Fri 8/7
3:35 pm-5:24 pm
Nonstop1h 49m
Chicago O'Hare Intl
Mon 8/10
6:39 pm-8:25 pm
Nonstop1h 46m
$199
MinneapolisChicago
MSP - ORD
MSPORD
Minneapolis St Paul
Wed 8/5
11:32 am-1:15 pm
Nonstop1h 43m
Chicago O'Hare Intl
Sun 8/9
8:50 am-10:36 am
Nonstop1h 46m
$216
MinneapolisChicago
MSP - MDW
MSPMDW
Minneapolis St Paul
Fri 9/18
4:40 pm-6:19 pm
Nonstop1h 39m
Chicago Midway
Sat 9/19
2:00 pm-3:40 pm
Nonstop1h 40m
$216
MinneapolisChicago
MSP - MDW
MSPMDW
Minneapolis St Paul
Fri 9/4
6:57 am-8:39 am
Nonstop1h 42m
Chicago Midway
Sat 9/5
4:52 pm-6:36 pm
Nonstop1h 44m
$216
Showing 1-10 of 59 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
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 June 30, 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 27% on airfare.
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 June 30, 2026.
The most flights from SA1 to CHI are scheduled on a Tuesday (122 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (28 on average).
How much does it cost to fly round-trip from Saint Paul to Chicago?
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 June 27, 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.
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 June 30, 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.
Crew
8.6
Boarding
8.1
Overall
7.9
Comfort
8.0
Food
7.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Boarding
8.1
Overall
7.9
Comfort
8.0
Food
7.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Boarding
8.1
Overall
7.9
Comfort
8.0
Food
7.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Boarding
8.1
Overall
7.9
Comfort
8.0
Food
7.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Boarding
8.1
Overall
7.9
Comfort
8.0
Food
7.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Boarding
8.1
Overall
7.9
Comfort
8.0
Food
7.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
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 locationsBenton Harbor
Hammond
Lansing
Merrillville
Valparaiso
Porter
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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 June 30, 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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Saint Paul and Chicago flights
Browse other Saint Paul and Chicago flight options. Last updated on June 30, 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 June 30, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$38 | Average$96 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$60 | Average$161 | FlexibilityNo cancel fee | On-time83% | |
| Cheapest$60 | Average$253 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$97 | Average$353 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$98 | Average$243 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$110 | Average$251 | FlexibilityNo cancel fee | On-time63% |