Cheap Flights from Milwaukee, WI to Chicago, IL from $100

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On Cheapflightsplus.com you will find 12 direct and 293 connecting flights from Milwaukee to Chicago. You can compare airfare deals from 5 airlines and multiple travel sites from $100, book and save on cheap plane tickets and last minute offers. Also check out MKE-CHI flight schedule to find best flight time, convenient departure and arrival airports.

Find One-Way and Round-Trip Milwaukee to Chicago Flight Deals

To find the cheapest one way airline ticket select the date with the lowest price on the calendar below and click «Find Flights». To search for round-trip flight deals click on the link «Check prices for return flights» and select the date of the return flight. Cheapest flights in November: $100 (one-way), $171 (round-trip).

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Best Flights from Milwaukee to Chicago Today

Take a look at the list of non stop flights and flights with layovers from Milwaukee to Chicago with the lowest price of $100. The fastest direct flight takes 1h 4m and the fastest connecting – 5h 48m.

Price	Departure	Arrival	Flight Duration	Airline	Flight
from $178 Find flight	05:15 Milwaukee General Mitchell	06:20 Chicago O'Hare International	1h 5m	United Airlines	UA5799
from $220 Find flight	06:00 Milwaukee General Mitchell	07:10 Chicago O'Hare International	1h 10m	United Airlines	UA5996
from $283 Find flight	10:54 Milwaukee General Mitchell	11:58 Chicago O'Hare International	1h 4m	United Airlines	UA5322
from $100 Find flight	10:35 Milwaukee General Mitchell	16:25 Chicago O'Hare International	5h 50m layover 2h 30m - Nashville	Spirit Airlines	NK2027 NK2028
from $120 Find flight	18:29 Milwaukee General Mitchell	17:15+1 день Chicago O'Hare International	22h 46m layover 19h 48m - Minneapolis	Sun Country Airlines	SY1816 SY261
from $134 Find flight	10:35 Milwaukee General Mitchell	23:29 Chicago O'Hare International	12h 54m layover 5h 47m - Nashville 0h 42m - Orlando	Spirit Airlines	NK2027 NK2241 NK2190
from $157 Find flight	09:15 Milwaukee General Mitchell	11:36+1 день Chicago O'Hare International	26h 21m layover 8h 42m - Baltimore 6h 4m - Los Angeles	Spirit Airlines	NK2442 NK2598 NK2192

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*Departure and arrival times - local. Prices indicated for one-way flights. Information updated on September 15, 2025

Flight Schedule Milwaukee (Wisconsin) to Chicago (Illinois)

Full flight schedule will help you in detecting at what time planes fly from Milwaukee to Chicago. You can also specify the concrete flights and airlines on the route and how long the flight actually is. Use the calendar for today, tomorrow or other specific date as some flights are available only on certain days of the week.

Departure	Flight Details	Flight Duration	Price
05:15 — 06:20	05:15 — 06:20 UA5799 United Airlines Milwaukee — Chicago	1h 5m	Find flight from$178
06:00 — 07:10	06:00 — 07:10 UA5996 United Airlines Milwaukee — Chicago	1h 10m	Find flight from$220
07:00 — 08:05	07:00 — 08:05 UA4803 United Airlines Milwaukee — Chicago	1h 5m	Find flight from$178
08:35 — 09:39	08:35 — 09:39 UA5402 United Airlines Milwaukee — Chicago	1h 4m	Find flight from$221
10:35 — 16:25	10:35 — 11:58 NK2027 Spirit Airlines Milwaukee — Nashville 2h 30m stop 14:28 — 16:25 NK2028 Spirit Airlines Nashville — Chicago	5h 50m including layover	Find flight from$100
10:45 — 11:50	10:45 — 11:50 UA4716 United Airlines Milwaukee — Chicago	1h 5m	Find flight from$221
10:50 — 12:00	10:50 — 12:00 UA5347 United Airlines Milwaukee — Chicago	1h 10m	Find flight from$220
10:50 — 12:00	10:50 — 12:00 UA4691 United Airlines Milwaukee — Chicago	1h 10m	Find flight from$222
10:54 — 11:58	10:54 — 11:58 UA5322 United Airlines Milwaukee — Chicago	1h 4m	Find flight from$283
12:10 — 13:15	12:10 — 13:15 UA4740 United Airlines Milwaukee — Chicago	1h 5m	Find flight from$178
14:59 — 11:36 +1 day	14:59 — 17:21 NK2075 Spirit Airlines Milwaukee — Los Angeles 12h 9m stop 05:30 — 11:36 NK2192 Spirit Airlines Los Angeles — Chicago	20h 37m including layover	Find flight from$113
15:45 — 16:50	15:45 — 16:50 UA5502 United Airlines Milwaukee — Chicago	1h 5m	Find flight from$221
17:31 — 18:36	17:31 — 18:36 UA5648 United Airlines Milwaukee — Chicago	1h 5m	Find flight from$178
17:31 — 18:36	17:31 — 18:36 UA3700 United Airlines Milwaukee — Chicago	1h 5m	Find flight from$222
18:29 — 17:15 +1 day	18:29 — 19:48 SY1816 Sun Country Airlines Milwaukee — Minneapolis 19h 48m stop 15:36 — 17:15 SY261 Sun Country Airlines Minneapolis — Chicago	22h 46m including layover	Find flight from$120

Departure	Arrival	Flight Details	Flight Time	Price
		stop stop	including layover	Find flight from$

*Departure and arrival times - local. Updated on September 15, 2025

Flight Information

Below we will explain in detail what the flights cost on the destination from Milwaukee to Chicago depends on and how to choose the most interesting flight option for you.

Distance between Milwaukee and Chicago is 120 miles. Time difference between the cities is 0h. Airplanes depart 05:15 to 21:20 from 3 Milwaukee airports and arrive 05:15 to 21:20 to 7 Chicago airports. Average flight time is 1h 5m.

The fastest flight 1h 4m
Average flight time 1h 5m
The earliest flight 05:15
The latest flight 21:20
Distance 75 ml

The cheapest months to travel to Chicago are june (from 100 $), july (from 120 $), may (from 157 $).

The most expensive months are november (from 266 $), october (from 220 $), september (from 178 $).

What is the lowest airfare Milwaukee to Chicago?

The cheapest plane ticket found by our users is $100. This airfare is for economy class on one-way NK2027 flight by Spirit Airlines for June 6, 2025 which leaves General Mitchell in Milwaukee at 10:35 am and arrives at Chicago O'Hare International at 16:25.

Economy class

$100

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Business class

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First class

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Popular Airlines on the Route

The flight Milwaukee — Chicago is served by 5 regular airlines and 2 low-cost airlines. Most of the flights on this route are operated by Alaska Airlines - 17 departures per week at the price of from $ 209 . And the most expensive tickets are offered by Alaska Airlines airline - from $ 814.

Direct flights

There are 12 nonstop flights on the route. The fastest direct flight is UA5402 by United Airlines takes 1h 4m and the cheapest is NK2027 by Spirit Airlines for $178.

UA - United Airlines

from $178

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Connecting Flights

There are 293 flights with layovers on the route. The fastest connecting flight is UA3470 by United Airlines takes 5h 48m and the cheapest is NK2027 by Spirit Airlines for $100.

AS - Alaska Airlines

from $209

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SY - Sun Country Airlines

from $120

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HA - Hawaiian Airlines

from $247

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UA - United Airlines

from $258

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NK - Spirit Airlines

from $100

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Airports

You can fly from Milwaukee to Chicago from 3 airports (Lawrence J Timmerman, Milwaukee General Mitchell, General Mitchell).

Milwaukee airports

Lawrence J Timmerman-MWC

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Milwaukee General Mitchell-ZML

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General Mitchell-MKE

from $100
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Chicago airports

O'Hare International-ORD

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Midway-MDW

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Dupage County-DPA

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Chicago FSS-CHI

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Merrill C Meigs (closed)-CGX

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Pal-Waukee-PWK

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Chicago NAS-NOH

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Airplanes

There are flights to Chicago from Milwaukee by 5 airlines that use 0 aircraft brands. They range from huge modern airplanes to small-sized.

Top Domestic Destinations from Milwaukee

You may also consider searching for discounted plane tickets to some other popular places from Milwaukee within United States.

Milwaukee — Orlando

from $67

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Milwaukee — Las Vegas

from $65

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Milwaukee — Phoenix

from $60

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Milwaukee — Denver

from $67

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Milwaukee — New York

from $54

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Milwaukee — Seattle

from $61

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Milwaukee — Dallas

from $71

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Milwaukee — Atlanta

from $77

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Milwaukee — Houston

from $61

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Milwaukee — Miami

from $70

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Top International Destinations from Milwaukee

Our state-of-the art metasearch will definitely provide you with the best airfare on international flights. We’re proud to partner with many reliable travel suppliers located outside the US what gives us an opportunity to offer the most competitive prices on far destinations.

Milwaukee — Toronto

from $57

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Milwaukee — London

from $60

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Milwaukee — Montreal

from $59

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Milwaukee — San Juan

from $71

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How to book a plane ticket yourself?

Fill in the search parameters — cities of departure and destination, departure and return dates and click «Find flights»
Select the best flight that you like. Please, check the airports of departure and arrival. Select the best fare, but pay attention to the following flight details - airports of departure and arrival, flight duration and layovers. Please use filters and sort to find the best flight.
Click «Buy» when you are ready — our system will redirect you to the site that sells the selected flight ticket.
Fill in all passenger and payment information — passport and contact information, please double check all passengers’ names and make a payment for your itinerary.
That's it — you will receive an email with your e-ticket usually within 10 minutes after your flight is confirmed. Please, print the e-ticket and have it with you at the airport. You would need to have only a passport and/or a required form of ID to travel. Please, check your Visa requirements if you travel outside of the United States or Canada.
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