$105+ Cheap flights from Chicago (CHI) to Milwaukee (MKE)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/12. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MKE
Oct 23 — Oct 301
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Milwaukee 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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Cheapest flights from Chicago to MilwaukeeExplore the most affordable flight options available from Chicago to Milwaukee. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 23, 2026.
Explore the most affordable flight options available from Chicago to Milwaukee. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 23, 2026.
This United Airlines deal was found by Cheapflights users on 9/22. 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 10/225:59 am -
Nonstop1h 08m
Mon 10/269:18 am -
Nonstop1h 12m
Deal found 9/22![United Airlines logo]()
$209
This Southwest deal was found by Cheapflights users on 9/18. 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 10/177:15 pm -
Nonstop0h 50m
Sat 10/246:00 am -
Nonstop0h 50m
Deal found 9/18![Southwest logo]()
$209
This American Airlines deal was found by Cheapflights users on 9/21. 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 11/55:30 pm -
Nonstop1h 05m
Thu 11/127:29 pm -
Nonstop1h 31m
Deal found 9/21![American Airlines logo]()
$210
This United Airlines deal was found by Cheapflights users on 9/21. 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 10/1410:25 am -
Nonstop1h 05m
Fri 10/1610:42 am -
Nonstop1h 11m
Deal found 9/21![United Airlines logo]()
$219
This United Airlines deal was found by Cheapflights users on 9/19. 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 12/310:25 am -
Nonstop1h 03m
Sun 12/65:53 pm -
Nonstop1h 12m
Deal found 9/19![United Airlines logo]()
$229
This Southwest deal was found by Cheapflights users on 9/21. 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 11/56:30 pm -
1 stop4h 40m
Thu 11/127:55 am -
1 stop6h 15m
Deal found 9/21![Southwest logo]()
$229
This Southwest deal was found by Cheapflights users on 9/21. 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 12/224:20 pm -
1 stop6h 45m
Thu 12/318:00 am -
1 stop4h 05m
Deal found 9/21![Southwest logo]()
$234
This American Airlines deal was found by Cheapflights users on 9/20. 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.
Fri 11/136:56 pm -
Nonstop1h 06m
Sun 11/155:04 am -
Nonstop1h 20m
Deal found 9/20![American Airlines logo]()
$239
This Southwest deal was found by Cheapflights users on 9/21. 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 10/229:55 am -
Nonstop0h 50m
Mon 10/265:55 am -
Nonstop0h 50m
Deal found 9/21![Southwest logo]()
$239
This United Airlines deal was found by Cheapflights users on 9/18. 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 10/188:15 pm -
Nonstop1h 10m
Sun 10/258:00 am -
Nonstop1h 12m
Deal found 9/18![United Airlines logo]()
$249
This United Airlines deal was found by Cheapflights users on 9/20. 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 10/105:59 am -
Nonstop1h 08m
Mon 10/126:32 pm -
Nonstop1h 13m
Deal found 9/20![United Airlines logo]()
$258
This Southwest deal was found by Cheapflights users on 9/20. 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 10/107:15 pm -
Nonstop0h 50m
Mon 10/125:55 am -
Nonstop0h 50m
Deal found 9/20![Southwest logo]()
$258
Best flights from Chicago to MilwaukeeDiscover carefully curated flight deals from Chicago to Milwaukee that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 23, 2026.
Discover carefully curated flight deals from Chicago to Milwaukee that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 23, 2026.
This United Airlines deal was found by Cheapflights users on 9/22. 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 10/218:57 am -
Nonstop1h 10m
Wed 10/286:18 pm -
Nonstop1h 11m
Deal found 9/22![United Airlines logo]()
$209
This American Airlines deal was found by Cheapflights users on 9/20. 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.
Wed 11/410:05 am -
Nonstop1h 03m
Wed 11/117:29 pm -
Nonstop1h 31m
Deal found 9/20![American Airlines logo]()
$209
This Southwest deal was found by Cheapflights users on 9/19. 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 11/129:15 pm -
Nonstop1h 00m
Tue 11/174:15 pm -
Nonstop0h 55m
Deal found 9/19![Southwest logo]()
$209
This United Airlines deal was found by Cheapflights users on 9/18. 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 10/105:59 pm -
Nonstop1h 10m
Mon 10/127:18 am -
Nonstop1h 11m
Deal found 9/18![United Airlines logo]()
$209
This American Airlines deal was found by Cheapflights users on 9/23. 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 10/226:59 am -
Nonstop1h 08m
Thu 10/297:45 am -
Nonstop1h 20m
Deal found 9/23![American Airlines logo]()
$209
This Southwest deal was found by Cheapflights users on 9/20. 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 11/49:10 pm -
Nonstop1h 05m
Wed 11/114:15 pm -
Nonstop0h 55m
Deal found 9/20![Southwest logo]()
$209
This United Airlines deal was found by Cheapflights users on 9/21. 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 11/44:40 pm -
Nonstop1h 03m
Thu 11/126:18 pm -
Nonstop1h 12m
Deal found 9/21![United Airlines logo]()
$209
This Southwest deal was found by Cheapflights users on 9/21. 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 11/59:15 pm -
Nonstop1h 00m
Thu 11/125:30 am -
Nonstop1h 05m
Deal found 9/21![Southwest logo]()
$209
This American Airlines deal was found by Cheapflights users on 9/22. 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 12/39:35 pm -
Nonstop1h 02m
Sun 12/68:40 am -
Nonstop1h 25m
Deal found 9/22![American Airlines logo]()
$229
This Southwest deal was found by Cheapflights users on 9/22. 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 10/2110:20 am -
Nonstop0h 45m
Wed 10/286:10 am -
Nonstop0h 50m
Deal found 9/22![Southwest logo]()
$209
This United Airlines deal was found by Cheapflights users on 9/19. 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 11/54:40 pm -
Nonstop1h 03m
Sun 11/810:48 am -
Nonstop1h 12m
Deal found 9/19![United Airlines logo]()
$229
This Southwest deal was found by Cheapflights users on 9/18. 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 10/177:15 pm -
Nonstop0h 50m
Sat 10/242:50 pm -
1 stop2h 55m
Deal found 9/18![Southwest logo]()
$219
This United Airlines deal was found by Cheapflights users on 9/18. 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 10/257:45 pm -
Nonstop1h 05m
Wed 10/288:50 am -
Nonstop1h 10m
Deal found 9/18![United Airlines logo]()
$229
This Southwest deal was found by Cheapflights users on 9/23. 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 10/229:55 am -
Nonstop0h 50m
Thu 10/291:05 pm -
1 stop4h 30m
Deal found 9/23![Southwest logo]()
$219
This Southwest deal was found by Cheapflights users on 9/19. 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 11/35:20 pm -
1 stop4h 55m
Tue 11/104:15 pm -
Nonstop0h 55m
Deal found 9/19![Southwest logo]()
$219
This Southwest deal was found by Cheapflights users on 9/18. 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.
Fri 10/169:40 pm -
Nonstop0h 55m
Fri 10/235:00 pm -
Nonstop0h 50m
Deal found 9/18![Southwest logo]()
$229
This United Airlines deal was found by Cheapflights users on 9/22. 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 10/158:57 am -
Nonstop1h 10m
Mon 10/197:18 am -
Nonstop1h 11m
Deal found 9/22![United Airlines logo]()
$299
This United Airlines deal was found by Cheapflights users on 9/20. 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 10/228:57 am -
Nonstop1h 10m
Mon 10/268:00 am -
Nonstop1h 12m
Deal found 9/20![United Airlines logo]()
$301
Last-minute flights from Chicago to MilwaukeeDiscover last-minute flight deals from Chicago to Milwaukee. Data last updated September 23, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Milwaukee. Data last updated September 23, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 9/18. 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 10/1010:25 am -
Nonstop0h 45m
Mon 10/125:55 am -
Nonstop0h 50m
Deal found 9/18![Southwest logo]()
$209
This United Airlines deal was found by Cheapflights users on 9/20. 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 10/105:59 am -
Nonstop1h 08m
Mon 10/126:32 pm -
Nonstop1h 13m
Deal found 9/20![United Airlines logo]()
$258
This United Airlines deal was found by Cheapflights users on 9/21. 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 10/1410:25 am -
Nonstop1h 05m
Fri 10/1610:42 am -
Nonstop1h 11m
Deal found 9/21![United Airlines logo]()
$219
This American Airlines deal was found by Cheapflights users on 9/18. 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.
Fri 10/166:52 pm -
Nonstop1h 06m
Fri 10/237:19 pm -
Nonstop1h 30m
Deal found 9/18![American Airlines logo]()
$229
This Southwest deal was found by Cheapflights users on 9/18. 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.
Fri 10/169:40 pm -
Nonstop0h 55m
Fri 10/235:00 pm -
Nonstop0h 50m
Deal found 9/18![Southwest logo]()
$229
This Southwest deal was found by Cheapflights users on 9/20. 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.
Fri 10/165:50 pm -
1 stop5h 20m
Sun 10/185:10 pm -
Nonstop0h 50m
Deal found 9/20![Southwest logo]()
$298
This American Airlines deal was found by Cheapflights users on 9/19. 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 10/179:34 pm -
Nonstop1h 08m
Sat 10/245:01 am -
Nonstop1h 13m
Deal found 9/19![American Airlines logo]()
$210
This Southwest deal was found by Cheapflights users on 9/18. 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 10/177:15 pm -
Nonstop0h 50m
Sat 10/242:50 pm -
1 stop2h 55m
Deal found 9/18![Southwest logo]()
$219
This United Airlines deal was found by Cheapflights users on 9/18. 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 10/188:15 pm -
Nonstop1h 10m
Sun 10/258:00 am -
Nonstop1h 12m
Deal found 9/18![United Airlines logo]()
$249
This Southwest deal was found by Cheapflights users on 9/20. 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 10/199:55 am -
Nonstop0h 50m
Mon 10/265:55 am -
Nonstop0h 50m
Deal found 9/20![Southwest logo]()
$268
This United Airlines deal was found by Cheapflights users on 9/22. 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 10/225:59 am -
Nonstop1h 08m
Mon 10/269:18 am -
Nonstop1h 12m
Deal found 9/22![United Airlines logo]()
$209
This Southwest deal was found by Cheapflights users on 9/21. 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 10/229:55 am -
Nonstop0h 50m
Mon 10/265:55 am -
Nonstop0h 50m
Deal found 9/21![Southwest logo]()
$239
One-way flights from Chicago to MilwaukeeSearch for one-way flight options from Chicago to Milwaukee. Find affordable one-way fares based on user searches. Data last updated September 23, 2026.
Search for one-way flight options from Chicago to Milwaukee. Find affordable one-way fares based on user searches. Data last updated September 23, 2026.
This United Airlines deal was found by Cheapflights users on 9/23. 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 10/2110:25 am -
Nonstop1h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![United Airlines logo]()
$105
This Southwest deal was found by Cheapflights users on 9/21. 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 12/2110:00 am -
Nonstop0h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Southwest logo]()
$105
This Southwest deal was found by Cheapflights users on 9/21. 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 11/56:30 pm -
1 stop4h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Southwest logo]()
$115
This American Airlines deal was found by Cheapflights users on 9/22. 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.
Fri 10/236:52 pm -
Nonstop1h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![American Airlines logo]()
$116
This Southwest deal was found by Cheapflights users on 9/22. 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 12/224:20 pm -
1 stop6h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Southwest logo]()
$120
This American Airlines deal was found by Cheapflights users on 9/19. 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.
Sun 10/186:59 am -
Nonstop1h 08m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![American Airlines logo]()
$125
This Southwest deal was found by Cheapflights users on 9/19. 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 10/189:40 pm -
Nonstop0h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![Southwest logo]()
$125
This Southwest deal was found by Cheapflights users on 9/21. 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.
Fri 11/206:30 pm -
1 stop4h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Southwest logo]()
$135
This Southwest deal was found by Cheapflights users on 9/21. 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 10/209:25 am -
1 stop6h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Southwest logo]()
$145
This United Airlines deal was found by Cheapflights users on 9/23. 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 10/207:45 pm -
Nonstop0h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![United Airlines logo]()
$150
This United Airlines deal was found by Cheapflights users on 9/18. 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 10/58:57 am -
Nonstop1h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![United Airlines logo]()
$154
This Southwest deal was found by Cheapflights users on 9/18. 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 10/59:40 pm -
Nonstop0h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Southwest logo]()
$154
Find flight deals from Chicago to Milwaukee
Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Milwaukee (MKE). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated September 23, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $209 (American Airlines) |
One-way from | $105 (United Airlines) |
Popular in | May |
Cheapest in | February |
Average price | $469 |
Good one-way deal | $239 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Milwaukee 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 7,457,451 searches. Data last updated September 23, 2026.
Use the filters below to find and compare flights from Chicago to Milwaukee that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoMilwaukee
ORD Chicago O'Hare Intl - MKE Milwaukee-Mitchell
ORDMKE
Chicago O'Hare Intl
Thu 11/12
4:40 pm-5:43 pm
Nonstop1h 03m
Milwaukee-Mitchell
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$105
ChicagoMilwaukee
MDW Chicago Midway - MKE Milwaukee-Mitchell
MDWMKE
Chicago Midway
Tue 12/22
9:30 pm-10:20 pm
Nonstop0h 50m
Milwaukee-Mitchell
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$105
ChicagoMilwaukee
MDW Chicago Midway - MKE Milwaukee-Mitchell
MDWMKE
Chicago Midway
Thu 10/22
9:55 am-10:45 am
Nonstop0h 50m
Milwaukee-Mitchell
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$105
ChicagoMilwaukee
MDW Chicago Midway - MKE Milwaukee-Mitchell
MDWMKE
Chicago Midway
Thu 11/19
10:10 am-11:00 am
Nonstop0h 50m
Milwaukee-Mitchell
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$105
ChicagoMilwaukee
MDW Chicago Midway - MKE Milwaukee-Mitchell
MDWMKE
Chicago Midway
Wed 11/18
10:10 am-11:00 am
Nonstop0h 50m
Milwaukee-Mitchell
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$105
Quickest round-trip
ChicagoMilwaukee
MDW Chicago Midway - MKE Milwaukee-Mitchell
MDWMKE
Chicago Midway
Wed 10/21
10:20 am-11:05 am
Nonstop0h 45m
Milwaukee-Mitchell
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$105
ChicagoMilwaukee
MDW Chicago Midway - MKE Milwaukee-Mitchell
MDWMKE
Chicago Midway
Sat 11/21
5:50 pm-11:10 pm
1 stop5h 20m
Milwaukee-Mitchell
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$115
ChicagoMilwaukee
ORD Chicago O'Hare Intl - MKE Milwaukee-Mitchell
ORDMKE
Chicago O'Hare Intl
Sat 12/19
4:40 pm-5:51 pm
Nonstop1h 11m
Milwaukee-Mitchell
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$125
ChicagoMilwaukee
ORD Chicago O'Hare Intl - MKE Milwaukee-Mitchell
ORDMKE
Chicago O'Hare Intl
Sun 11/22
7:30 am-8:36 am
Nonstop1h 06m
Milwaukee-Mitchell
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$125
ChicagoMilwaukee
MDW Chicago Midway - MKE Milwaukee-Mitchell
MDWMKE
Chicago Midway
Tue 10/20
9:25 am-3:25 pm
1 stop6h 00m
Milwaukee-Mitchell
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$145
Showing 1-10 of 37 resultsSorted by cheapest first
Compare providers for flights from Chicago to Milwaukee
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Milwaukee in September.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Chicago-Milwaukee flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Milwaukee flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Milwaukee flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago-Milwaukee flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Milwaukee flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Chicago to Milwaukee
Have a flexible travel schedule? Discover the best time to fly to Milwaukee from Chicago with our price prediction graph.
CHI-MKE
ORD-MKE
MDW-MKE
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 Chicago to Milwaukee
CHI-MKE
ORD-MKE
MDW-MKE
What is the cheapest time of day to fly from CHI to MKE?
Find hourly flight availability from Chicago to Milwaukee. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 23, 2026.
Unlike in the evening, when flights are generally more expensive, you can save up to 39% on flights from Chicago to Milwaukee by exploring options for tickets in the afternoon.
Weekly flight availability from Chicago to Milwaukee
Explore weekly flight availability from Chicago to Milwaukee. 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 September 23, 2026.
The most flights from CHI to MKE are scheduled on a Tuesday (54 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (27 on average).
Reviews of airlines servicing Milwaukee
Get insights into the airlines that provide service to Milwaukee. 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 Milwaukee. Reviews last updated September 23, 2026.
Read through reviews of airlines operating flights from Chicago to Milwaukee, such as United Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Comfort
7.3
Food
6.7
Boarding
7.7
Overall
7.4
Crew
8.1
Entertainment
7.1
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
Comfort
7.3
Food
6.7
Boarding
7.7
Overall
7.4
Crew
8.1
Entertainment
7.1
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
Related info for your journey
Find useful and relevant information for your journey from Chicago to Milwaukee. 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 Milwaukee?
Book flights to Milwaukee if you plan to visit one of these locationsPort Washington
Sheboygan
New Berlin
Oak Creek
Wauwatosa
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Complete your trip
Complete your trip to Milwaukee by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Milwaukee by cabin class
Find flights from Chicago to Milwaukee, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Other flights to Milwaukee
Explore flights to Milwaukee departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on September 23, 2026.
Chicago and Milwaukee flights
Browse other Chicago and Milwaukee flight options. Last updated on September 23, 2026.
Other flights from Chicago
Browse through other flights departing from Chicago. Flights are based on user searches made on Cheapflights and were last updated on September 23, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 2 airlines flying from Chicago to Milwaukee
Discover the top 2 airlines that operate flights from Chicago to Milwaukee. 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 7,457,451 searches. Data last updated September 23, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$179 | Average$207 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$179 | Average$318 | FlexibilityNo cancel fee | On-time69% |