$81+ Cheap flights from Milwaukee (MKE) to Chicago (CHI)
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 10/21. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — CHI
Oct 23 — Oct 301
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
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.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 September 23, 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 September 23, 2026.
This United Airlines deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 10/57:18 am -
Nonstop1h 11m
Mon 10/1210:00 pm -
Nonstop0h 59m
Deal found 9/17![United Airlines logo]()
$183
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.
Sat 10/177:45 am -
Nonstop1h 20m
Sat 10/241:20 pm -
Nonstop1h 04m
Deal found 9/20![American Airlines logo]()
$209
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.
Sat 10/176:00 am -
Nonstop0h 50m
Sat 10/2410:25 am -
Nonstop0h 45m
Deal found 9/22![Southwest logo]()
$209
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.
Sat 10/107:19 pm -
Nonstop1h 30m
Mon 10/125:29 pm -
Nonstop1h 07m
Deal found 9/18![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.
Fri 10/166:15 am -
Nonstop1h 11m
Mon 10/195:59 am -
Nonstop1h 08m
Deal found 9/21![United Airlines logo]()
$219
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 10/138:20 am -
1 stop7h 10m
Tue 10/2010:20 am -
Nonstop0h 45m
Deal found 9/21![Southwest logo]()
$225
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.
Fri 10/166:15 am -
Nonstop1h 11m
Fri 10/2310:00 pm -
Nonstop0h 59m
Deal found 9/18![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.
Fri 10/165:00 pm -
Nonstop0h 50m
Fri 10/239:40 pm -
Nonstop0h 55m
Deal found 9/18![Southwest 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.
Tue 10/204:30 pm -
1 stop5h 30m
Tue 10/272:45 pm -
2 stops8h 00m
Deal found 9/22![Southwest logo]()
$234
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.
Fri 12/252:07 pm -
Nonstop1h 21m
Mon 12/2812:30 pm -
Nonstop1h 07m
Deal found 9/19![American Airlines logo]()
$239
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 11/256:18 pm -
Nonstop1h 12m
Sun 11/295:55 pm -
Nonstop1h 03m
Deal found 9/21![United Airlines logo]()
$249
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 10/102:50 pm -
1 stop2h 55m
Mon 10/129:55 am -
Nonstop0h 50m
Deal found 9/18![Southwest logo]()
$249
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 September 23, 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 September 23, 2026.
This Southwest deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 10/102:05 pm -
Nonstop0h 50m
Mon 10/129:40 pm -
Nonstop0h 55m
Deal found 9/17![Southwest logo]()
$172
This United Airlines deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 10/57:18 am -
Nonstop1h 11m
Mon 10/1210:00 pm -
Nonstop0h 59m
Deal found 9/17![United Airlines logo]()
$183
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.
Tue 11/108:40 am -
Nonstop1h 25m
Thu 11/129:35 pm -
Nonstop1h 02m
Deal found 9/20![American Airlines logo]()
$209
This United Airlines deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 10/1512:05 pm -
Nonstop1h 10m
Thu 10/225:59 am -
Nonstop1h 08m
Deal found 9/17![United Airlines logo]()
$183
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 10/136:10 am -
Nonstop0h 50m
Tue 10/2010:20 am -
Nonstop0h 45m
Deal found 9/21![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.
Sat 10/108:30 am -
Nonstop1h 11m
Mon 10/124:30 pm -
Nonstop1h 10m
Deal found 9/19![United Airlines logo]()
$209
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 10/204:30 pm -
1 stop5h 30m
Tue 10/278:45 pm -
Nonstop0h 50m
Deal found 9/22![Southwest logo]()
$219
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 10/176:00 am -
Nonstop0h 50m
Sat 10/246:45 am -
1 stop3h 45m
Deal found 9/20![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.
Wed 12/308:20 am -
Nonstop1h 20m
Sun 1/34:40 pm -
Nonstop1h 11m
Deal found 9/18![United Airlines 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.
Tue 2/97:45 am -
1 stop4h 55m
Mon 2/159:45 pm -
Nonstop0h 45m
Deal found 9/20![Southwest logo]()
$219
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.
Tue 11/106:20 am -
Nonstop1h 00m
Thu 11/126:30 am -
1 stop3h 10m
Deal found 9/20![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.
Sat 3/2010:45 am -
Nonstop1h 00m
Sun 3/282:10 pm -
Nonstop0h 54m
Deal found 9/18![United Airlines logo]()
$249
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.
Wed 11/2510:48 am -
Nonstop1h 11m
Mon 11/309:20 pm -
Nonstop0h 55m
Deal found 9/18![United Airlines logo]()
$249
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.
Sat 10/107:00 am -
1 stop5h 22m
Mon 10/125:29 pm -
Nonstop1h 07m
Deal found 9/18![American Airlines logo]()
$471
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.
Tue 10/610:42 am -
Nonstop1h 11m
Sat 10/1012:40 pm -
Nonstop1h 03m
Deal found 9/21![United Airlines logo]()
$307
This United Airlines deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 10/3110:48 am -
Nonstop1h 12m
Wed 11/47:00 am -
1 stop13h 59m
Deal found 9/17![United Airlines logo]()
$433
Last-minute flights from Milwaukee to ChicagoDiscover last-minute flight deals from Milwaukee to Chicago. Data last updated September 23, 2026 and is based on user searches.
Discover last-minute flight deals from Milwaukee to Chicago. Data last updated September 23, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 10/57:18 am -
Nonstop1h 11m
Mon 10/1210:00 pm -
Nonstop0h 59m
Deal found 9/17![United Airlines logo]()
$183
This Southwest deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 10/102:05 pm -
Nonstop0h 50m
Mon 10/129:40 pm -
Nonstop0h 55m
Deal found 9/17![Southwest logo]()
$172
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.
Sat 10/107:19 pm -
Nonstop1h 30m
Mon 10/125:29 pm -
Nonstop1h 07m
Deal found 9/18![American Airlines logo]()
$210
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 10/138:20 am -
1 stop7h 10m
Tue 10/2010:20 am -
Nonstop0h 45m
Deal found 9/21![Southwest logo]()
$225
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.
Fri 10/166:15 am -
Nonstop1h 11m
Mon 10/195:59 am -
Nonstop1h 08m
Deal found 9/21![United Airlines 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.
Fri 10/166:15 am -
Nonstop1h 11m
Fri 10/2310:00 pm -
Nonstop0h 59m
Deal found 9/18![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.
Fri 10/165:00 pm -
Nonstop0h 50m
Fri 10/239:40 pm -
Nonstop0h 55m
Deal found 9/18![Southwest logo]()
$229
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 10/177:45 am -
Nonstop1h 20m
Sat 10/241:20 pm -
Nonstop1h 04m
Deal found 9/19![American Airlines logo]()
$209
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.
Sat 10/176:00 am -
Nonstop0h 50m
Sat 10/2410:25 am -
Nonstop0h 45m
Deal found 9/22![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.
Sun 10/186:32 pm -
Nonstop1h 13m
Sun 10/257:45 pm -
Nonstop1h 05m
Deal found 9/20![United Airlines logo]()
$249
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 10/204:30 pm -
1 stop5h 30m
Tue 10/272:45 pm -
2 stops8h 00m
Deal found 9/22![Southwest logo]()
$234
This United Airlines deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 9/17![United Airlines logo]()
$251
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 September 23, 2026.
Search for one-way flight options from Milwaukee to Chicago. 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 9/17. Clicking the “Pick Dates” 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 10/212:20 pm -
Nonstop1h 11m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![United Airlines logo]()
$81
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 10/2211:42 am -
Nonstop1h 11m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![American 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.
Thu 11/55:30 am -
Nonstop1h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Southwest logo]()
$105
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.
Fri 1/87:36 am -
Nonstop1h 29m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![American Airlines logo]()
$115
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.
Sun 10/256:18 pm -
Nonstop1h 11m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![United Airlines 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.
Sun 10/255:55 am -
Nonstop0h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![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 11/207:55 am -
1 stop6h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Southwest logo]()
$135
This Southwest deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 10/214:00 pm -
Nonstop0h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Southwest logo]()
$144
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.
Tue 10/202:58 pm -
Nonstop1h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![American 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.
Fri 10/22:20 pm -
Nonstop1h 11m
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 10/55:55 am -
Nonstop0h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Southwest logo]()
$154
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.
Mon 10/197:18 am -
Nonstop1h 11m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![United Airlines logo]()
$160
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 September 23, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $209 (American Airlines) |
One-way from | $81 (United Airlines) |
Good round-trip deal | $372 or less |
Good one-way deal | $204 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 7,457,451 searches. Data last updated September 23, 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
MilwaukeeChicago
MKE Milwaukee-Mitchell - ORD Chicago O'Hare Intl
MKEORD
Milwaukee-Mitchell
Tue 11/17
2:23 pm-3:35 pm
Nonstop1h 12m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$105
MilwaukeeChicago
MKE Milwaukee-Mitchell - MDW Chicago Midway
MKEMDW
Milwaukee-Mitchell
Thu 11/5
5:30 am-6:35 am
Nonstop1h 05m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$105
MilwaukeeChicago
MKE Milwaukee-Mitchell - MDW Chicago Midway
MKEMDW
Milwaukee-Mitchell
Mon 12/21
5:45 am-6:45 am
Nonstop1h 00m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$105
MilwaukeeChicago
MKE Milwaukee-Mitchell - ORD Chicago O'Hare Intl
MKEORD
Milwaukee-Mitchell
Fri 10/16
2:20 pm-3:31 pm
Nonstop1h 11m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$115
MilwaukeeChicago
MKE Milwaukee-Mitchell - MDW Chicago Midway
MKEMDW
Milwaukee-Mitchell
Wed 11/18
8:00 am-12:05 pm
1 stop4h 05m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$115
Quickest round-trip
MilwaukeeChicago
MKE Milwaukee-Mitchell - MDW Chicago Midway
MKEMDW
Milwaukee-Mitchell
Fri 10/16
5:55 am-6:45 am
Nonstop0h 50m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$115
MilwaukeeChicago
MKE Milwaukee-Mitchell - MDW Chicago Midway
MKEMDW
Milwaukee-Mitchell
Tue 11/17
4:05 pm-9:35 pm
1 stop5h 30m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$115
MilwaukeeChicago
MKE Milwaukee-Mitchell - ORD Chicago O'Hare Intl
MKEORD
Milwaukee-Mitchell
Sun 10/25
6:18 pm-7:29 pm
Nonstop1h 11m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$125
MilwaukeeChicago
MKE Milwaukee-Mitchell - ORD Chicago O'Hare Intl
MKEORD
Milwaukee-Mitchell
Thu 3/18
7:00 am-8:00 am
Nonstop1h 00m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$125
MilwaukeeChicago
MKE Milwaukee-Mitchell - ORD Chicago O'Hare Intl
MKEORD
Milwaukee-Mitchell
Fri 12/18
5:00 am-6:23 am
Nonstop1h 23m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$125
Showing 1-10 of 36 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 September.
| 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 September 23, 2026.
It’s optimal to fly from Milwaukee to Chicago in the morning. By choosing this option you can save up to 45% 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 September 23, 2026.
The most flights from MKE to CHI are scheduled on a Tuesday (57 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (32 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 11% 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 September 19, 2026.
Travelers seeking maximum savings on their Milwaukee to Chicago flight should consider departing on Wednesday afternoons 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 September 23, 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.
Overall
7.0
Crew
7.9
Food
6.4
Entertainment
6.8
Boarding
7.4
Comfort
7.2
Reviews
1 / 20
2.0
MediocreAnonymous,Aug 2025
BNA - ORD
Overall
7.0
Crew
7.9
Food
6.4
Entertainment
6.8
Boarding
7.4
Comfort
7.2
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
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on September 23, 2026.
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Milwaukee and Chicago flights
Browse other Milwaukee and Chicago flight options. Last updated on September 23, 2026.
Other flights from Milwaukee
Browse through other flights departing from Milwaukee. 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 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 7,457,451 searches. Data last updated September 23, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$171 | Average$229 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$179 | Average$219 | FlexibilityNo cancel fee | On-time71% |