$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 10/20. Fares are subject to change and may not be available on all flights or dates of travel.
MSP — CHI
Aug 28 — Sep 41
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
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 December or October, booked 25 days in advance, depart on a Friday or Thursday and return on a Friday
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 July 29, 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 July 29, 2026.
This Southwest deal was found by Cheapflights users on 7/28. 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.
Thu 9/35:45 am
MSP
- MDW
Nonstop1h 25m
Southwest
Mon 9/78:00 am
MDW
- MSP
Nonstop1h 45m
Southwest
Deal found 7/28![Southwest logo]()
$117
This United Airlines deal was found by Cheapflights users on 7/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/2511:21 am
MSP
- ORD
Nonstop1h 46m
United Airlines
Thu 8/276:59 am
ORD
- MSP
Nonstop1h 40m
United Airlines
Deal found 7/27![United Airlines logo]()
$117
This American Airlines deal was found by Cheapflights users on 7/27. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/207:02 am
MSP
- ORD
Nonstop1h 52m
American Airlines
Mon 8/2410:40 pm
ORD
- MSP
Nonstop1h 44m
American Airlines
Deal found 7/27![American Airlines logo]()
$118
This Delta deal was found by Cheapflights users on 7/27. 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.
Sun 9/62:20 pm
MSP
- MDW
Nonstop1h 37m
Delta
Tue 9/89:59 am
MDW
- MSP
Nonstop1h 41m
Delta
Deal found 7/27![Delta logo]()
$122
This Delta deal was found by Cheapflights users on 7/27. 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.
Sun 9/68:10 pm
MSP
- ORD
Nonstop1h 37m
Delta
Wed 9/912:29 pm
ORD
- MSP
Nonstop1h 42m
Delta
Deal found 7/27![Delta logo]()
$122
This Southwest deal was found by Cheapflights users on 7/27. 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 8/256:15 am
MSP
- MDW
Nonstop1h 25m
Southwest
Wed 8/265:20 pm
MDW
- MSP
1 stop5h 30m
Southwest
Deal found 7/27![Southwest logo]()
$127
This Delta deal was found by Cheapflights users on 7/24. 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 9/193:25 pm
MSP
- ORD
Nonstop1h 34m
Delta
Thu 10/112:29 pm
ORD
- MSP
Nonstop1h 42m
Delta
Deal found 7/24![Delta logo]()
$127
This Southwest deal was found by Cheapflights users on 7/25. 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.
Tue 9/296:15 am
MSP
- MDW
Nonstop1h 25m
Southwest
Tue 10/67:55 am
MDW
- MSP
2 stops6h 55m
Southwest
Deal found 7/25![Southwest logo]()
$128
This Southwest deal was found by Cheapflights users on 7/28. 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.
Tue 8/257:00 am
MSP
- MDW
2 stops9h 00m
Southwest
Wed 9/25:10 pm
MDW
- MSP
Nonstop1h 30m
Southwest
Deal found 7/28![Southwest logo]()
$132
This Delta deal was found by Cheapflights users on 7/24. 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 9/27:00 am
MSP
- ORD
Nonstop1h 30m
Delta
Sun 9/68:28 am
ORD
- MSP
Nonstop1h 35m
Delta
Deal found 7/24![Delta logo]()
$132
This Southwest deal was found by Cheapflights users on 7/29. 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 9/58:05 am
MSP
- MDW
1 stop8h 05m
Southwest
Mon 9/78:00 am
MDW
- MSP
Nonstop1h 45m
Southwest
Deal found 7/29![Southwest logo]()
$133
This Southwest deal was found by Cheapflights users on 7/28. 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.
Thu 8/205:45 am
MSP
- MDW
Nonstop1h 25m
Southwest
Mon 8/248:00 am
MDW
- MSP
Nonstop1h 45m
Southwest
Deal found 7/28![Southwest logo]()
$134
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 July 29, 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 July 29, 2026.
This Delta deal was found by Cheapflights users on 7/27. 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.
Thu 9/36:57 am
MSP
- MDW
Nonstop1h 42m
Delta
Tue 9/87:13 pm
MDW
- MSP
Nonstop1h 47m
Delta
Deal found 7/27![Delta logo]()
$117
This Southwest deal was found by Cheapflights users on 7/27. 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.
Thu 10/810:40 am
MSP
- MDW
Nonstop1h 30m
Southwest
Tue 10/131:05 pm
MDW
- MSP
Nonstop1h 25m
Southwest
Deal found 7/27![Southwest logo]()
$117
This United Airlines deal was found by Cheapflights users on 7/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/188:00 am
MSP
- ORD
Nonstop1h 44m
United Airlines
Tue 8/256:59 am
ORD
- MSP
Nonstop1h 40m
United Airlines
Deal found 7/27![United Airlines logo]()
$117
This Southwest deal was found by Cheapflights users on 7/24. 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 8/225:30 am
MSP
- MDW
Nonstop1h 25m
Southwest
Mon 8/248:00 am
MDW
- MSP
Nonstop1h 45m
Southwest
Deal found 7/24![Southwest logo]()
$117
This Delta deal was found by Cheapflights users on 7/26. 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.
Wed 10/217:00 am
MSP
- MDW
Nonstop1h 44m
Delta
Sat 10/2410:01 am
MDW
- MSP
Nonstop1h 41m
Delta
Deal found 7/26![Delta logo]()
$117
This United Airlines deal was found by Cheapflights users on 7/25. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/199:45 am
MSP
- ORD
Nonstop1h 44m
United Airlines
Tue 9/227:00 am
ORD
- MSP
Nonstop1h 39m
United Airlines
Deal found 7/25![United Airlines logo]()
$117
This Delta deal was found by Cheapflights users on 7/28. 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 9/16:57 am
MSP
- MDW
Nonstop1h 42m
Delta
Thu 9/39:59 am
MDW
- MSP
Nonstop1h 43m
Delta
Deal found 7/28![Delta logo]()
$117
This Southwest deal was found by Cheapflights users on 7/25. 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.
Tue 8/186:15 am
MSP
- MDW
Nonstop1h 25m
Southwest
Thu 8/205:55 am
MDW
- MSP
1 stop4h 20m
Southwest
Deal found 7/25![Southwest logo]()
$127
This Delta deal was found by Cheapflights users on 7/27. 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.
Mon 10/128:00 pm
MSP
- ORD
Nonstop1h 36m
Delta
Thu 10/156:20 am
ORD
- MSP
Nonstop1h 34m
Delta
Deal found 7/27![Delta logo]()
$117
This Southwest deal was found by Cheapflights users on 7/28. 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.
Thu 9/34:45 pm
MSP
- MDW
1 stop5h 15m
Southwest
Mon 9/78:00 am
MDW
- MSP
Nonstop1h 45m
Southwest
Deal found 7/28![Southwest logo]()
$127
This Kiwi.com deal was found by Cheapflights users on 7/25. 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.
Wed 8/269:57 pm
MSP
- RFD
2 stops17h 12m
Multiple Airlines
Sun 8/309:35 pm
RFD
- MSP
1 stop22h 02m
Multiple Airlines
Deal found 7/25![Multiple Airlines logo]()
$324
This Southwest deal was found by Cheapflights users on 7/25. 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 10/310:35 am
MSP
- MDW
Nonstop1h 30m
Southwest
Tue 10/67:55 am
MDW
- MSP
2 stops6h 55m
Southwest
Deal found 7/25![Southwest logo]()
$128
This United Airlines deal was found by Cheapflights users on 7/24. 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.
Sun 8/239:45 am
MSP
- ORD
Nonstop1h 44m
United Airlines
Mon 8/246:59 am
ORD
- MSP
Nonstop1h 40m
United Airlines
Deal found 7/24![United Airlines logo]()
$172
This Southwest deal was found by Cheapflights users on 7/26. 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.
Wed 8/267:00 am
MSP
- MDW
2 stops9h 00m
Southwest
Tue 9/18:30 am
MDW
- MSP
Nonstop1h 40m
Southwest
Deal found 7/26![Southwest logo]()
$132
This United Airlines deal was found by Cheapflights users on 7/25. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/116:55 pm
MSP
- ORD
Nonstop1h 45m
United Airlines
Sat 10/314:00 pm
ORD
- MSP
Nonstop1h 39m
United Airlines
Deal found 7/25![United Airlines logo]()
$172
This Southwest deal was found by Cheapflights users on 7/28. 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 8/269:05 am
MSP
- MDW
2 stops6h 55m
Southwest
Wed 9/22:20 pm
MDW
- MSP
Nonstop1h 30m
Southwest
Deal found 7/28![Southwest logo]()
$132
This Delta deal was found by Cheapflights users on 7/26. 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.
Wed 9/96:55 am
MSP
- ORD
Nonstop1h 35m
Delta
Wed 9/168:55 am
ORD
- MSP
1 stop4h 34m
Delta
Deal found 7/26![Delta logo]()
$177
This Southwest deal was found by Cheapflights users on 7/28. 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 9/98:00 am
MSP
- MDW
1 stop5h 55m
Southwest
Wed 9/95:20 pm
MDW
- MSP
1 stop5h 35m
Southwest
Deal found 7/28![Southwest logo]()
$137
This Delta deal was found by Cheapflights users on 7/27. 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 8/256:04 am
MSP
- ORD
1 stop4h 38m
Delta
Sat 8/296:00 am
ORD
- MSP
Nonstop1h 30m
Delta
Deal found 7/27![Delta logo]()
$177
This Southwest deal was found by Cheapflights users on 7/25. 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.
Tue 9/298:00 am
MSP
- MDW
1 stop3h 50m
Southwest
Tue 10/67:55 am
MDW
- MSP
2 stops6h 55m
Southwest
Deal found 7/25![Southwest logo]()
$138
This Delta deal was found by Cheapflights users on 7/28. 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 9/96:55 am
MSP
- ORD
Nonstop1h 35m
Delta
Wed 9/91:55 pm
ORD
- MSP
1 stop6h 49m
Delta
Deal found 7/28![Delta logo]()
$177
This Delta deal was found by Cheapflights users on 7/24. 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 9/96:05 am
MSP
- ORD
1 stop6h 54m
Delta
Mon 9/148:25 pm
ORD
- MSP
Nonstop1h 43m
Delta
Deal found 7/24![Delta logo]()
$182
This Kiwi.com deal was found by Cheapflights users on 7/27. 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.
Wed 8/199:57 pm
MSP
- RFD
2 stops17h 12m
Multiple Airlines
Sun 8/239:35 pm
RFD
- MSP
1 stop22h 02m
Multiple Airlines
Deal found 7/27![Multiple Airlines logo]()
$353
This Delta deal was found by Cheapflights users on 7/24. 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 9/206:55 am
MSP
- ORD
Nonstop1h 35m
Delta
Sat 10/35:50 pm
ORD
- MSP
Nonstop1h 40m
Delta
Deal found 7/24![Delta logo]()
$182
This Delta deal was found by Cheapflights users on 7/25. 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 8/257:00 am
MSP
- ORD
Nonstop1h 30m
Delta
Sun 8/308:24 pm
ORD
- MSP
Nonstop1h 51m
Delta
Deal found 7/25![Delta logo]()
$182
This Kiwi.com deal was found by Cheapflights users on 7/26. 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.
Thu 9/107:00 am
MSP
- RFD
2 stops13h 39m
Multiple Airlines
Sun 9/139:29 pm
RFD
- MSP
1 stop21h 39m
Multiple Airlines
Deal found 7/26![Multiple Airlines logo]()
$358
This Kiwi.com deal was found by Cheapflights users on 7/24. 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 10/1510:26 pm
MSP
- RFD
1 stop13h 01m
Multiple Airlines
Sun 10/189:33 pm
RFD
- MSP
1 stop14h 39m
Multiple Airlines
Deal found 7/24![Multiple Airlines logo]()
$376
This Delta deal was found by Cheapflights users on 7/27. 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.
Fri 9/48:10 pm
MSP
- ORD
Nonstop1h 37m
Delta
Mon 9/76:59 am
ORD
- MSP
1 stop6h 21m
Delta
Deal found 7/27![Delta logo]()
$232
This Kiwi.com deal was found by Cheapflights users on 7/24. 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 9/29:57 pm
MSP
- RFD
2 stops17h 06m
Multiple Airlines
Sun 9/69:29 pm
RFD
- MSP
1 stop19h 36m
Multiple Airlines
Deal found 7/24![Multiple Airlines logo]()
$419
This Kiwi.com deal was found by Cheapflights users on 7/26. 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.
Thu 10/16:25 am
MSP
- RFD
1 stop13h 48m
Multiple Airlines
Sun 10/49:36 pm
RFD
- MSP
1 stop21h 32m
Multiple Airlines
Deal found 7/26![Multiple Airlines logo]()
$428
Last-minute flights from Saint Paul to ChicagoDiscover last-minute flight deals from Saint Paul to Chicago. Data last updated July 29, 2026 and is based on user searches.
Discover last-minute flight deals from Saint Paul to Chicago. Data last updated July 29, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 7/24. 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 8/154:00 pm
MSP
- ORD
Nonstop1h 41m
Delta
Mon 8/178:24 pm
ORD
- MSP
Nonstop1h 51m
Delta
Deal found 7/24![Delta logo]()
$127
This deal was found by Cheapflights users on 7/26. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/1810:30 am
MSP
- ORD
Nonstop1h 47m
Sun Country Air
Thu 8/205:29 pm
ORD
- MSP
Nonstop1h 36m
Sun Country Air
Deal found 7/26![Sun Country Air logo]()
$138
This Delta deal was found by Cheapflights users on 7/27. 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 8/197:00 am
MSP
- ORD
Nonstop1h 30m
Delta
Thu 8/206:00 am
ORD
- MSP
Nonstop1h 30m
Delta
Deal found 7/27![Delta logo]()
$137
This American Airlines deal was found by Cheapflights users on 7/27. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/207:02 am
MSP
- ORD
Nonstop1h 52m
American Airlines
Mon 8/2410:40 pm
ORD
- MSP
Nonstop1h 44m
American Airlines
Deal found 7/27![American Airlines logo]()
$118
This Southwest deal was found by Cheapflights users on 7/28. 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.
Thu 8/205:45 am
MSP
- MDW
Nonstop1h 25m
Southwest
Mon 8/248:00 am
MDW
- MSP
Nonstop1h 45m
Southwest
Deal found 7/28![Southwest logo]()
$134
This Delta deal was found by Cheapflights users on 7/25. 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.
Thu 8/206:57 am
MSP
- MDW
Nonstop1h 42m
Delta
Mon 8/241:51 pm
MDW
- MSP
Nonstop1h 44m
Delta
Deal found 7/25![Delta logo]()
$138
This Delta deal was found by Cheapflights users on 7/28. 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 8/256:57 am
MSP
- MDW
Nonstop1h 42m
Delta
Tue 9/19:59 am
MDW
- MSP
Nonstop1h 43m
Delta
Deal found 7/28![Delta logo]()
$117
This Delta deal was found by Cheapflights users on 7/27. 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 8/257:00 am
MSP
- ORD
Nonstop1h 30m
Delta
Wed 8/266:00 am
ORD
- MSP
Nonstop1h 30m
Delta
Deal found 7/27![Delta logo]()
$117
This Southwest deal was found by Cheapflights users on 7/27. 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 8/256:15 am
MSP
- MDW
Nonstop1h 25m
Southwest
Wed 8/265:20 pm
MDW
- MSP
1 stop5h 30m
Southwest
Deal found 7/27![Southwest logo]()
$127
This Southwest deal was found by Cheapflights users on 7/28. 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.
Tue 8/257:00 am
MSP
- MDW
2 stops9h 00m
Southwest
Tue 9/15:10 pm
MDW
- MSP
Nonstop1h 30m
Southwest
Deal found 7/28![Southwest logo]()
$132
This Southwest deal was found by Cheapflights users on 7/28. 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.
Tue 8/257:00 am
MSP
- MDW
2 stops9h 00m
Southwest
Wed 9/24:40 pm
MDW
- MSP
1 stop5h 45m
Southwest
Deal found 7/28![Southwest logo]()
$142
This Delta deal was found by Cheapflights users on 7/27. 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.
Mon 8/314:00 pm
MSP
- ORD
Nonstop1h 41m
Delta
Sun 9/66:00 am
ORD
- MSP
Nonstop1h 30m
Delta
Deal found 7/27![Delta logo]()
$122
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 July 29, 2026.
Search for one-way flight options from Saint Paul to Chicago. Find affordable one-way fares based on user searches. Data last updated July 29, 2026.
This Southwest deal was found by Cheapflights users on 7/28. 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.
Tue 9/15:35 pm
MSP
- MDW
Nonstop1h 30m
Southwest
Deal found 7/28![Southwest logo]()
$59
This Delta deal was found by Cheapflights users on 7/28. 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.
Sat 9/267:00 am
MSP
- ORD
Nonstop1h 38m
Delta
Deal found 7/28![Delta logo]()
$59
This Delta deal was found by Cheapflights users on 7/28. 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 10/303:08 pm
MSP
- MDW
Nonstop1h 39m
Delta
Deal found 7/28![Delta logo]()
$64
This Delta deal was found by Cheapflights users on 7/28. 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 9/118:00 pm
MSP
- ORD
Nonstop1h 33m
Delta
Deal found 7/28![Delta logo]()
$64
This Southwest deal was found by Cheapflights users on 7/27. 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 9/2612:30 pm
MSP
- MDW
1 stop6h 00m
Southwest
Deal found 7/27![Southwest logo]()
$69
This Sun Country Air deal was found by Cheapflights users on 7/28. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/253:35 pm
MSP
- ORD
Nonstop1h 39m
Sun Country Air
Deal found 7/28![Sun Country Air logo]()
$69
This Trip.com deal was found by Cheapflights users on 7/26. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/318:05 am
MSP
- ORD
Nonstop1h 38m
Sun Country Air
Deal found 7/26![Sun Country Air logo]()
$72
This Southwest deal was found by Cheapflights users on 7/28. 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.
Sat 9/510:25 am
MSP
- MDW
1 stop8h 55m
Southwest
Deal found 7/28![Southwest logo]()
$74
This Southwest deal was found by Cheapflights users on 7/27. 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 9/77:40 am
MSP
- MDW
Nonstop1h 30m
Southwest
Deal found 7/27![Southwest logo]()
$76
This Delta deal was found by Cheapflights users on 7/24. 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 9/144:40 pm
MSP
- MDW
Nonstop1h 39m
Delta
Deal found 7/24![Delta logo]()
$79
This Super.com deal was found by Cheapflights users on 7/26. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/113:05 pm
MSP
- ORD
Nonstop1h 39m
Sun Country Air
Deal found 7/26![Sun Country Air logo]()
$79
This Southwest deal was found by Cheapflights users on 7/24. 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 10/246:50 am
MSP
- MDW
2 stops11h 10m
Southwest
Deal found 7/24![Southwest logo]()
$80
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 July 29, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $117 (Delta) |
One-way from | $59 (Southwest) |
Popular in | March |
Cheapest in | December |
Average price | $257 |
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 July 29, 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
Thu 9/3
6:57 am-8:39 am
Nonstop1h 42m
Chicago Midway
Tue 9/8
7:13 pm-9:00 pm
Nonstop1h 47m
$117
Quickest round-trip
MinneapolisChicago
MSP - MDW
MSPMDW
Minneapolis St Paul
Thu 10/8
10:40 am-12:10 pm
Nonstop1h 30m
Chicago Midway
Tue 10/13
1:05 pm-2:30 pm
Nonstop1h 25m
$117
MinneapolisChicago
MSP - ORD
MSPORD
Minneapolis St Paul
Tue 8/18
8:00 am-9:44 am
Nonstop1h 44m
Chicago O'Hare Intl
Tue 8/25
6:59 am-8:39 am
Nonstop1h 40m
$117
MinneapolisChicago
MSP - MDW
MSPMDW
Minneapolis St Paul
Sat 8/22
5:30 am-6:55 am
Nonstop1h 25m
Chicago Midway
Mon 8/24
8:00 am-9:45 am
Nonstop1h 45m
$117
MinneapolisChicago
MSP - MDW
MSPMDW
Minneapolis St Paul
Wed 10/21
7:00 am-8:44 am
Nonstop1h 44m
Chicago Midway
Sat 10/24
10:01 am-11:42 am
Nonstop1h 41m
$117
MinneapolisChicago
MSP - ORD
MSPORD
Minneapolis St Paul
Sat 9/19
9:45 am-11:29 am
Nonstop1h 44m
Chicago O'Hare Intl
Tue 9/22
7:00 am-8:39 am
Nonstop1h 39m
$117
MinneapolisChicago
MSP - MDW
MSPMDW
Minneapolis St Paul
Tue 9/1
6:57 am-8:39 am
Nonstop1h 42m
Chicago Midway
Thu 9/3
9:59 am-11:42 am
Nonstop1h 43m
$117
MinneapolisChicago
MSP - ORD
MSPORD
Minneapolis St Paul
Mon 10/12
8:00 pm-9:36 pm
Nonstop1h 36m
Chicago O'Hare Intl
Thu 10/15
6:20 am-7:54 am
Nonstop1h 34m
$117
MinneapolisChicago
MSP - MDW
MSPMDW
Minneapolis St Paul
Tue 8/18
6:15 am-7:40 am
Nonstop1h 25m
Chicago Midway
Thu 8/20
5:55 am-10:15 am
1 stop4h 20m
$127
MinneapolisChicago
MSP - MDW
MSPMDW
Minneapolis St Paul
Thu 9/3
4:45 pm-10:00 pm
1 stop5h 15m
Chicago Midway
Mon 9/7
8:00 am-9:45 am
Nonstop1h 45m
$127
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
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 July 29, 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 36% 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 July 29, 2026.
The most flights from SA1 to CHI are scheduled on a Monday (126 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (43 on average).
How much does it cost to fly round-trip from Saint Paul to Chicago?
Airfare is below average for this route at the moment.
Saint Paul to Chicago flights typically cost between $154 and $311 in September.The cheapest round-trip price found within the last 5 days was $117 on Delta (Sep 3-Sep 8).
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 July 25, 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. Tuesday evenings flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated July 29, 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.
Food
7.0
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Crew
8.6
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Crew
8.6
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Crew
8.6
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Crew
8.6
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Crew
8.6
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Crew
8.6
Overall
8.0
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
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Merrillville
Valparaiso
Hammond
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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 July 29, 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 July 29, 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 July 29, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$38 | Average$96 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$58 | Average$267 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$62 | Average$164 | FlexibilityNo cancel fee | On-time83% | |
| Cheapest$99 | Average$245 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$117 | Average$281 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$117 | Average$364 | FlexibilityNo cancel fee | On-time71% |