$75+ Cheap flights from Milwaukee (MKE) 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 9/9. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — CHI
Sep 9 — Sep 161
Round-trip
1 adult, Economy
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Find cheap flights from Milwaukee 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.Cheap flight deals from Milwaukee to Chicago
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Cheapest flights from Milwaukee to ChicagoExplore the most affordable flight options available from Milwaukee to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 10, 2026.
Explore the most affordable flight options available from Milwaukee to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 10, 2026.
This Southwest deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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 -
Nonstop0h 45m
Mon 9/78:40 pm -
Nonstop0h 45m
Deal found 8/10![Southwest logo]()
$150
This Southwest deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” 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 9/51:30 pm -
Nonstop0h 50m
Sun 9/68:35 pm -
Nonstop0h 45m
Deal found 8/9![Southwest logo]()
$164
This Southwest deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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 9/51:00 pm -
1 stop6h 20m
Mon 9/78:40 pm -
Nonstop0h 45m
Deal found 8/10![Southwest logo]()
$165
This American Airlines deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” 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 9/57:00 pm -
Nonstop1h 29m
Sun 9/67:58 pm -
Nonstop1h 02m
Deal found 8/6![American Airlines logo]()
$179
This American Airlines deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” 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 9/111:18 pm -
Nonstop1h 21m
Tue 9/158:51 pm -
Nonstop1h 03m
Deal found 8/6![American Airlines logo]()
$189
This Southwest deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” 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 -
Nonstop0h 45m
Sat 9/56:10 pm -
Nonstop0h 55m
Deal found 8/8![Southwest logo]()
$189
This United Airlines deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” 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.
Fri 9/45:00 am -
Nonstop1h 10m
Fri 9/115:45 pm -
Nonstop1h 09m
Deal found 8/7![United Airlines logo]()
$197
This Southwest deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” 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 9/44:20 pm -
Nonstop0h 50m
Fri 9/1110:10 am -
Nonstop0h 50m
Deal found 8/6![Southwest logo]()
$197
This American Airlines deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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 9/27:00 pm -
Nonstop1h 29m
Wed 9/98:51 pm -
Nonstop1h 03m
Deal found 8/5![American Airlines logo]()
$199
This Southwest deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” 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 9/34:20 pm -
Nonstop0h 50m
Thu 9/108:40 pm -
Nonstop0h 45m
Deal found 8/6![Southwest logo]()
$199
This American Airlines deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” 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 8/301:17 pm -
Nonstop1h 19m
Sun 9/66:50 am -
Nonstop0h 59m
Deal found 8/6![American Airlines logo]()
$204
This American Airlines deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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 9/511:32 am -
Nonstop1h 11m
Mon 9/77:58 pm -
Nonstop1h 02m
Deal found 8/10![American Airlines logo]()
$205
Best flights from Milwaukee to ChicagoDiscover carefully curated flight deals from Milwaukee to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 10, 2026.
Discover carefully curated flight deals from Milwaukee to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 10, 2026.
This Southwest deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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 -
Nonstop0h 45m
Mon 9/78:40 pm -
Nonstop0h 45m
Deal found 8/10![Southwest logo]()
$150
This American Airlines deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” 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 9/57:00 pm -
Nonstop1h 29m
Sun 9/67:58 pm -
Nonstop1h 02m
Deal found 8/8![American Airlines logo]()
$179
This United Airlines deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” 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 9/298:30 am -
Nonstop1h 11m
Wed 9/305:59 am -
Nonstop1h 08m
Deal found 8/6![United Airlines logo]()
$199
This Southwest deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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 9/55:45 am -
Nonstop0h 45m
Mon 9/78:40 pm -
Nonstop0h 45m
Deal found 8/10![Southwest logo]()
$150
This Southwest deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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 9/67:00 am -
Nonstop0h 50m
Sun 9/68:35 pm -
Nonstop0h 45m
Deal found 8/5![Southwest logo]()
$179
This American Airlines deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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 9/27:00 pm -
Nonstop1h 29m
Wed 9/98:51 pm -
Nonstop1h 03m
Deal found 8/5![American Airlines logo]()
$199
This United Airlines deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” 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.
Fri 9/47:18 am -
Nonstop1h 11m
Sat 9/54:15 pm -
Nonstop1h 10m
Deal found 8/8![United Airlines logo]()
$204
This Southwest deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” 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 9/55:45 am -
Nonstop0h 45m
Sun 9/611:10 am -
Nonstop0h 45m
Deal found 8/9![Southwest logo]()
$179
This United Airlines deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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.
Fri 9/186:47 pm -
Nonstop1h 13m
Sun 9/2010:25 am -
Nonstop1h 05m
Deal found 8/5![United Airlines logo]()
$222
This Southwest deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” 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 9/44:20 pm -
Nonstop0h 50m
Fri 9/1110:10 am -
Nonstop0h 50m
Deal found 8/6![Southwest logo]()
$197
This Southwest deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” 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 9/26:40 am -
Nonstop0h 50m
Tue 9/810:15 am -
Nonstop0h 50m
Deal found 8/6![Southwest logo]()
$199
This Southwest deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” 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 9/34:20 pm -
Nonstop0h 50m
Thu 9/108:40 pm -
Nonstop0h 45m
Deal found 8/6![Southwest logo]()
$199
This United Airlines deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” 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 10/319:23 am -
Nonstop1h 12m
Wed 11/47:45 pm -
Nonstop1h 05m
Deal found 8/6![United Airlines logo]()
$269
This Southwest deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” 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 9/55:45 am -
Nonstop0h 45m
Sat 9/1210:15 am -
Nonstop0h 50m
Deal found 8/8![Southwest logo]()
$204
This Southwest deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” 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 9/34:50 pm -
1 stop5h 10m
Sat 9/52:25 pm -
1 stop4h 05m
Deal found 8/8![Southwest logo]()
$209
This KAYAK deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” 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.
Sun 9/137:00 am -
1 stop7h 18m
Fri 9/188:51 pm -
Nonstop1h 03m
Deal found 8/6![American Airlines logo]()
$405
This United Airlines deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” 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 10/137:18 am -
Nonstop1h 11m
Tue 1/268:00 pm -
Nonstop0h 54m
Deal found 8/8![United Airlines logo]()
$409
This United Airlines deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” 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 10/137:18 am -
Nonstop1h 11m
Fri 1/2912:45 pm -
Nonstop0h 58m
Deal found 8/8![United Airlines logo]()
$409
This United Airlines deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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.
Fri 9/1110:30 am -
Nonstop1h 11m
Tue 9/156:00 am -
1 stop12h 23m
Deal found 8/5![United Airlines logo]()
$442
Last-minute flights from Milwaukee to ChicagoDiscover last-minute flight deals from Milwaukee to Chicago. Data last updated August 10, 2026 and is based on user searches.
Discover last-minute flight deals from Milwaukee to Chicago. Data last updated August 10, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” 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 8/301:17 pm -
Nonstop1h 19m
Sun 9/66:50 am -
Nonstop0h 59m
Deal found 8/6![American Airlines logo]()
$204
This American Airlines deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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 9/31:17 pm -
Nonstop1h 19m
Mon 9/77:58 pm -
Nonstop1h 02m
Deal found 8/10![American Airlines logo]()
$151
This Southwest deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” 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 -
Nonstop0h 45m
Sat 9/56:10 pm -
Nonstop0h 55m
Deal found 8/8![Southwest logo]()
$189
This United Airlines deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” 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 9/310:19 am -
Nonstop1h 11m
Thu 9/1010:25 am -
Nonstop1h 05m
Deal found 8/6![United Airlines logo]()
$199
This Southwest deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” 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 9/34:20 pm -
Nonstop0h 50m
Thu 9/108:40 pm -
Nonstop0h 45m
Deal found 8/6![Southwest logo]()
$199
This United Airlines deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” 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.
Fri 9/45:00 am -
Nonstop1h 10m
Fri 9/115:45 pm -
Nonstop1h 09m
Deal found 8/7![United Airlines logo]()
$197
This Southwest deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” 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 9/44:20 pm -
Nonstop0h 50m
Fri 9/1110:10 am -
Nonstop0h 50m
Deal found 8/6![Southwest logo]()
$197
This Southwest deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” 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 9/51:30 pm -
Nonstop0h 50m
Sun 9/68:35 pm -
Nonstop0h 45m
Deal found 8/9![Southwest logo]()
$164
This American Airlines deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” 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 9/57:00 pm -
Nonstop1h 29m
Sun 9/67:58 pm -
Nonstop1h 02m
Deal found 8/6![American Airlines logo]()
$179
This American Airlines deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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 9/511:32 am -
Nonstop1h 11m
Mon 9/77:58 pm -
Nonstop1h 02m
Deal found 8/10![American Airlines logo]()
$205
This United Airlines deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” 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 9/106:00 am -
Nonstop1h 11m
Sun 9/138:50 am -
Nonstop1h 10m
Deal found 8/7![United Airlines logo]()
$214
This American Airlines deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” 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 9/111:18 pm -
Nonstop1h 21m
Tue 9/158:51 pm -
Nonstop1h 03m
Deal found 8/6![American Airlines logo]()
$189
One-way flights from Milwaukee to ChicagoSearch for one-way flight options from Milwaukee to Chicago. Find affordable one-way fares based on user searches. Data last updated August 10, 2026.
Search for one-way flight options from Milwaukee to Chicago. Find affordable one-way fares based on user searches. Data last updated August 10, 2026.
This Southwest deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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 9/96:40 am -
Nonstop0h 50m
Deal found 8/10![Southwest logo]()
$75
This American Airlines deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” 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 9/56:00 am -
Nonstop1h 21m
Deal found 8/6![American Airlines logo]()
$90
This Southwest deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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 9/51:30 pm -
Nonstop0h 50m
Deal found 8/5![Southwest logo]()
$90
This American Airlines deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” 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 8/2911:32 am -
Nonstop1h 11m
Deal found 8/6![American Airlines logo]()
$100
This Southwest deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” 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 9/61:20 pm -
1 stop6h 20m
Deal found 8/7![Southwest logo]()
$100
This United Airlines deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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.
Fri 9/45:17 pm -
Nonstop1h 13m
Deal found 8/5![United Airlines logo]()
$108
This Southwest deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” 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 9/45:45 am -
Nonstop0h 45m
Deal found 8/7![Southwest logo]()
$108
This Southwest deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” 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 9/1210:35 am -
1 stop3h 30m
Deal found 8/7![Southwest logo]()
$110
This United Airlines deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” 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.
Fri 10/95:00 am -
Nonstop1h 10m
Deal found 8/10![United Airlines logo]()
$115
This American Airlines deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” 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 9/195:03 am -
Nonstop1h 22m
Deal found 8/9![American Airlines logo]()
$116
This American Airlines deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” 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 9/66:00 am -
Nonstop1h 21m
Deal found 8/7![American Airlines logo]()
$125
This Flysmarter deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1910:55 am -
1 stop8h 06m
Deal found 8/9![JetBlue logo]()
$128
Find flight deals from Milwaukee to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Milwaukee (MKE) to Chicago (CHI). 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 August 10, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $150 (Southwest) |
One-way from | $75 (Southwest) |
Good round-trip deal | $349 or less |
Good one-way deal | $199 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Milwaukee 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 August 10, 2026.
Use the filters below to find and compare flights from Milwaukee to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
MilwaukeeChicago
MKE Milwaukee-Mitchell - MDW Chicago Midway
MKEMDW
Milwaukee-Mitchell
Thu 9/3
5:45 am-6:30 am
Nonstop0h 45m
Chicago Midway
Mon 9/7
8:40 pm-9:25 pm
Nonstop0h 45m
$150
MilwaukeeChicago
MKE Milwaukee-Mitchell - MDW Chicago Midway
MKEMDW
Milwaukee-Mitchell
Sat 9/5
5:45 am-6:30 am
Nonstop0h 45m
Chicago Midway
Mon 9/7
8:40 pm-9:25 pm
Nonstop0h 45m
$150
MilwaukeeChicago
MKE Milwaukee-Mitchell - ORD Chicago O'Hare Intl
MKEORD
Milwaukee-Mitchell
Sat 9/5
7:00 pm-8:29 pm
Nonstop1h 29m
Chicago O'Hare Intl
Sun 9/6
7:58 pm-9:00 pm
Nonstop1h 02m
$179
MilwaukeeChicago
MKE Milwaukee-Mitchell - MDW Chicago Midway
MKEMDW
Milwaukee-Mitchell
Sun 9/6
7:00 am-7:50 am
Nonstop0h 50m
Chicago Midway
Sun 9/6
8:35 pm-9:20 pm
Nonstop0h 45m
$179
MilwaukeeChicago
MKE Milwaukee-Mitchell - MDW Chicago Midway
MKEMDW
Milwaukee-Mitchell
Sat 9/5
5:45 am-6:30 am
Nonstop0h 45m
Chicago Midway
Sun 9/6
11:10 am-11:55 am
Nonstop0h 45m
$179
MilwaukeeChicago
MKE Milwaukee-Mitchell - MDW Chicago Midway
MKEMDW
Milwaukee-Mitchell
Fri 9/4
4:20 pm-5:10 pm
Nonstop0h 50m
Chicago Midway
Fri 9/11
10:10 am-11:00 am
Nonstop0h 50m
$197
MilwaukeeChicago
MKE Milwaukee-Mitchell - ORD Chicago O'Hare Intl
MKEORD
Milwaukee-Mitchell
Tue 9/29
8:30 am-9:41 am
Nonstop1h 11m
Chicago O'Hare Intl
Wed 9/30
5:59 am-7:07 am
Nonstop1h 08m
$199
MilwaukeeChicago
MKE Milwaukee-Mitchell - ORD Chicago O'Hare Intl
MKEORD
Milwaukee-Mitchell
Wed 9/2
7:00 pm-8:29 pm
Nonstop1h 29m
Chicago O'Hare Intl
Wed 9/9
8:51 pm-9:54 pm
Nonstop1h 03m
$199
MilwaukeeChicago
MKE Milwaukee-Mitchell - MDW Chicago Midway
MKEMDW
Milwaukee-Mitchell
Wed 9/2
6:40 am-7:30 am
Nonstop0h 50m
Chicago Midway
Tue 9/8
10:15 am-11:05 am
Nonstop0h 50m
$199
MilwaukeeChicago
MKE Milwaukee-Mitchell - MDW Chicago Midway
MKEMDW
Milwaukee-Mitchell
Thu 9/3
4:20 pm-5:10 pm
Nonstop0h 50m
Chicago Midway
Thu 9/10
8:40 pm-9:25 pm
Nonstop0h 45m
$199
Showing 1-10 of 38 resultsSorted by cheapest first
Compare providers for flights from Milwaukee to Chicago
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 Milwaukee to Chicago in August.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Milwaukee-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Milwaukee-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Milwaukee-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Milwaukee-Chicago 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 Milwaukee-Chicago 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 Milwaukee to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Milwaukee with our price prediction graph.
MKE-CHI
MKE-MDW
MKE-ORD
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 Milwaukee to Chicago
MKE-CHI
MKE-MDW
MKE-ORD
What is the cheapest time of day to fly from MKE to CHI?
Find hourly flight availability from Milwaukee 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 August 10, 2026.
It’s optimal to fly from Milwaukee to Chicago in the morning. By choosing this option you can save up to 41% on the cost of your flight, compared to a flight in the evening.
Weekly flight availability from Milwaukee to Chicago
Explore weekly flight availability from Milwaukee 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 August 10, 2026.
The most flights from MKE to CHI are scheduled on a Sunday (61 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (21 on average).
How often are flights from Milwaukee to Chicago delayed?
About 14% of weekly flights between Milwaukee and Chicago have experienced delays in the past year, with the average delay time being 123 minutes.
What is the most punctual flight time for Milwaukee to Chicago flights?
Historically, flights departing at night are less likely to be delayed, whereas flights leaving in the early afternoon tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Tuesday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Milwaukee to Chicago flights?
Over the last year, United Airlines have had the lowest number of delays on this route, with just 12% of flights being delayed.
What is the cheapest day to fly from Milwaukee to Chicago?
Use this chart to determine the cheapest time to fly round-trip from Milwaukee to Chicago. Price data was last updated on August 8, 2026.
Travelers seeking maximum savings on their Milwaukee to Chicago flight should consider departing on Saturday at noon when fares are most often at their lowest. Saturday 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 August 10, 2026.
Read reviews from past customers who have flown American Airlines from Milwaukee to Chicago. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Food
6.4
Entertainment
6.8
Overall
7.1
Comfort
7.2
Boarding
7.5
Crew
7.9
Reviews
1 / 20
2.0
MediocreAnonymous,Aug 2025
BNA - ORD
Food
6.4
Entertainment
6.8
Overall
7.1
Comfort
7.2
Boarding
7.5
Crew
7.9
Reviews
1 / 20
2.0
MediocreAnonymous,Aug 2025
BNA - ORD
Related info for your journey
Find useful and relevant information for your journey from Milwaukee 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
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
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Other flights to Chicago
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Milwaukee and Chicago flights
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Top 2 airlines flying from Milwaukee to Chicago
Discover the top 2 airlines that operate flights from Milwaukee 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 August 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$171 | Average$219 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$179 | Average$205 | FlexibilityNo cancel fee | On-time71% |