What is the cheapest airline that flies from Wisconsin to Chicago?

Sun Country Air, Delta, and United Airlines are the most popular carriers operating from Wisconsin to Chicago

How many flights depart from Wisconsin to Chicago on average per day?

As of July 2025, there are 175 flights per day flying from Wisconsin to Chicago. The most common time of day flights depart is 10:00AM, with 45% of flights taking off in the afternoon.

How many flights depart from Wisconsin to Chicago on average per week?

1,225 flights are operational weekly from Wisconsin to Chicago as of July 2025. The most popular departure day for this route is Thu, with 22% of flights per week taking off on this day.

How long does it take to fly to Chicago?

Average flight duration from Wisconsin to Chicago depends on which airport you fly into and out of. Flying from Madison to Chicago O'Hare Intl Airport is 1h 03m on average, while flying from Milwaukee to Chicago O'Hare Intl Airport is 1h 05m on average. Chicago O'Hare Intl Airport is the most popular airport in Chicago.

When did momondo last update prices for flights from Wisconsin to Chicago?

Prices for flights from Wisconsin to Chicago are refreshed on a daily basis.

How many operators does momondo search for flights from Wisconsin to Chicago?

As of July 2025, there are 5 operators available to choose from for flights from Wisconsin to Chicago.

How old do you have to be to fly from Wisconsin to Chicago?

The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Wisconsin to Chicago.

What documentation or ID do you need to fly to Chicago?

The required travel and health documents for your Chicago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

$46 Cheap Flights from Wisconsin to Chicago in 2025

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Find the cheapest flights from Wisconsin to Chicago

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

4:48 pm - 6:26 pmMSP-ORD

1h 38mnonstop

6:08 pm - 7:50 pmORD-MSP

1h 42mnonstop

$91Sun Country Air

Find Deal

vie., nov. 14 - dom., nov. 16

8:54 am - 10:39 amMSP-ORD

1h 45mnonstop

7:40 pm - 9:22 pmORD-MSP

1h 42mnonstop

$92Sun Country Air

Find Deal

dom., nov. 9 - jue., nov. 13

11:32 am - 1:08 pmMSP-MDW

1h 36mnonstop

9:20 am - 10:59 amMDW-MSP

1h 39mnonstop

$97Delta

Find Deal

sáb., nov. 8 - mié., nov. 12

8:00 pm - 9:35 pmMSP-ORD

1h 35mnonstop

6:10 am - 7:38 amORD-MSP

1h 28mnonstop

$97Delta

Find Deal

sáb., sep. 6 - mar., sep. 9

10:25 am - 11:50 amMSP-MDW

1h 25mnonstop

7:25 am - 2:30 pmMDW-MSP

7h 05m1 stop

$107Southwest

Find Deal

sáb., sep. 6 - mar., sep. 9

10:50 am - 12:15 pmMSP-MDW

1h 25mnonstop

8:40 pm - 10:15 pmMDW-MSP

1h 35mnonstop

$110Southwest

Find Deal

mié., sep. 10 - lun., sep. 15

6:00 am - 7:43 amMSP-ORD

1h 43mnonstop

7:19 am - 8:55 amORD-MSP

1h 36mnonstop

$110United Airlines

Find Deal

dom., sep. 7 - mié., sep. 10

5:55 pm - 7:39 pmMSP-ORD

1h 44mnonstop

7:19 am - 8:49 amORD-MSP

1h 30mnonstop

$112American Airlines

Find Deal

mié., sep. 10 - dom., sep. 14

5:00 am - 6:32 amMSP-ORD

1h 32mnonstop

7:36 am - 9:15 amORD-MSP

1h 39mnonstop

$117American Airlines

Find Deal

jue., oct. 30 - jue., oct. 30

6:00 am - 7:43 amMSP-ORD

1h 43mnonstop

7:19 am - 8:55 amORD-MSP

1h 36mnonstop

$119United Airlines

Find Deal

lun., sep. 1 - mar., sep. 2

Sun Country Air flights from Wisconsin to Chicago

Our best Sun Country Air deals on Wisconsin to Chicago flight tickets

Sun Country Air

Nov 14

MSP4:48 pmMinneapolis St Paul

1h 38m

ORD6:26 pmChicago O'Hare Intl

Nov 16

ORD6:08 pmChicago O'Hare Intl

1h 42m

MSP7:50 pmMinneapolis St Paul

$91

Find similar

Sun Country Air

Nov 9

MSP8:54 amMinneapolis St Paul

1h 45m

ORD10:39 amChicago O'Hare Intl

Nov 13

ORD7:40 pmChicago O'Hare Intl

1h 42m

MSP9:22 pmMinneapolis St Paul

$92

Find similar

Sun Country Air

Aug 18

MSP4:00 pmMinneapolis St Paul

1h 39m

ORD5:39 pmChicago O'Hare Intl

Aug 25

ORD10:10 amChicago O'Hare Intl

1h 47m

MSP11:57 amMinneapolis St Paul

$103

Find similar

Delta flights from Wisconsin to Chicago

Our best Delta deals on Wisconsin to Chicago flight tickets

Delta

Sep 6

MSP8:00 pmMinneapolis St Paul

1h 35m

ORD9:35 pmChicago O'Hare Intl

Sep 9

ORD6:10 amChicago O'Hare Intl

1h 28m

MSP7:38 amMinneapolis St Paul

$97

Find similar

Delta

Aug 24

MSP6:55 amMinneapolis St Paul

1h 29m

ORD8:24 amChicago O'Hare Intl

Aug 27

ORD8:25 amChicago O'Hare Intl

1h 34m

MSP9:59 amMinneapolis St Paul

$120

Find similar

Delta

Jan 19

MSP11:30 amMinneapolis St Paul

1h 38m

MDW1:08 pmChicago Midway

Jan 21

MDW6:45 pmChicago Midway

1h 40m

MSP8:25 pmMinneapolis St Paul

$124

Find similar

Fly from

Fly to

Route

Depart

Return

Price

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

vie. 11/14

4:48 pm-6:26 pm

Nonstop1h 38m

Chicago O'Hare Intl

dom. 11/16

6:08 pm-7:50 pm

Nonstop1h 42m

$91

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

dom. 11/9

8:54 am-10:39 am

Nonstop1h 45m

Chicago O'Hare Intl

jue. 11/13

7:40 pm-9:22 pm

Nonstop1h 42m

$92

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

sáb. 11/8

11:32 am-1:08 pm

Nonstop1h 36m

Chicago Midway

mié. 11/12

9:20 am-10:59 am

Nonstop1h 39m

$97

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

sáb. 9/6

8:00 pm-9:35 pm

Nonstop1h 35m

Chicago O'Hare Intl

mar. 9/9

6:10 am-7:38 am

Nonstop1h 28m

$97

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

sáb. 9/6

10:25 am-11:50 am

Nonstop1h 25m

Chicago Midway

mar. 9/9

7:25 am-2:30 pm

1 stop7h 05m

$107

MinneapolisChicago

MSP - MDW

MSPMDW

Minneapolis St Paul

mié. 9/10

10:50 am-12:15 pm

Nonstop1h 25m

Chicago Midway

lun. 9/15

8:40 pm-10:15 pm

Nonstop1h 35m

$110

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

dom. 9/7

6:00 am-7:43 am

Nonstop1h 43m

Chicago O'Hare Intl

mié. 9/10

7:19 am-8:55 am

Nonstop1h 36m

$110

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

mié. 9/10

5:55 pm-7:39 pm

Nonstop1h 44m

Chicago O'Hare Intl

dom. 9/14

7:19 am-8:49 am

Nonstop1h 30m

$112

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

jue. 10/30

5:00 am-6:32 am

Nonstop1h 32m

Chicago O'Hare Intl

jue. 10/30

7:36 am-9:15 am

Nonstop1h 39m

$117

MinneapolisChicago

MSP - ORD

MSPORD

Minneapolis St Paul

lun. 9/1

6:00 am-7:43 am

Nonstop1h 43m

Chicago O'Hare Intl

mar. 9/2

7:19 am-8:55 am

Nonstop1h 36m

$119

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Wisconsin to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

Other information

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as $460. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Wisconsin to Chicago for around $568.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the morning. Flights from Wisconsin to Chicago during this time can be as low as $476. In contrast, the most expensive time of day to depart to Chicago is in the evening when prices are around $807.

What is the cheapest Wisconsin to Chicago flight route?

Fly from Milwaukee-Mitchell to Chicago O'Hare Intl for the best Wisconsin - Chicago flight prices

What cabin class options are available on Wisconsin to Chicago flights?

There are 4 cabin classes available to choose from on Wisconsin to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Wisconsin to Chicago flights?

No. A direct flight is the cheapest option for a flight between Wisconsin to Chicago.

Cheap Wisconsin to Chicago flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Wisconsin to Chicago

Best Price Found	$46
Fastest flight time	1h 03m
Direct flights	Every day
Airports in Chicago	2 airports

The best one-way flight to Chicago from Wisconsin in the past 72 hours is $46. The best round-trip flight deal from Wisconsin to Chicago found on momondo in the last 72 hours is $91.

The fastest flight from Wisconsin to Chicago takes 1h 03m

Direct flights go from Wisconsin to Chicago every day.

There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)

Search flight deals

When did momondo last update prices for flights from Wisconsin to Chicago?
Prices for flights from Wisconsin to Chicago are refreshed on a daily basis.
How many operators does momondo search for flights from Wisconsin to Chicago?
As of July 2025, there are 5 operators available to choose from for flights from Wisconsin to Chicago.
How old do you have to be to fly from Wisconsin to Chicago?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Wisconsin to Chicago.
What documentation or ID do you need to fly to Chicago?
The required travel and health documents for your Chicago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.
What is the most popular plane model from Wisconsin to Chicago?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Wisconsin to Chicago is Airbus A320-100/200 (9.52% of total bookings). The next most popular plane models are Embraer 175 (7.56%), Embraer 175 (Enhanced Winglets) (7.39%), and Embraer 170 (6.09%).

Best airlines flying from Wisconsin to Chicago

Compare and see reviews for airlines that fly from Wisconsin to Chicago with momondo

Airline	Rating	Free Cancellation	Price
United Airlines	PriceFrom $179	Free Cancellation	Rating 7.4 8,900 reviews		Search United Airlines flights
American Airlines	PriceFrom $179	Free Cancellation	Rating 7.2 10,000 reviews		Search American Airlines flights

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Hammond

Benton Harbor

Saint Joseph

Portage

Lansing

Schererville

Valparaiso

Crown Point

Munster

Chesterton

Monticello

Porter

Griffith

Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Wisconsin to Chicago?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Wisconsin to Chicago. Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from Wisconsin to Chicago with flexible booking policies on momondo?

Yes. All flights to Chicago from Wisconsin on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Wisconsin to Chicago?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Wisconsin.

I’m not ready to book a flight from Wisconsin to Chicago right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Chicago from Wisconsin. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

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Cheap flights from Wisconsin to Chicago from $46

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Wisconsin to Chicago departing on 9/13. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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Big names and deals

Filter for what you want

Filter for what you want

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Find the cheapest flights from Wisconsin to Chicago

Cheap round-trip flights

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Cheap last minute flights

Cheap direct flights

Sun Country Air flights from Wisconsin to Chicago

Our best Sun Country Air deals on Wisconsin to Chicago flight tickets

Delta flights from Wisconsin to Chicago

Our best Delta deals on Wisconsin to Chicago flight tickets

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Use the filters below to find and compare flights from Wisconsin to Chicago that are best for you.

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How to get the cheapest flight ticket from Wisconsin to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest day to depart on your flight to Chicago?

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the morning. Flights from Wisconsin to Chicago during this time can be as low as $476. In contrast, the most expensive time of day to depart to Chicago is in the evening when prices are around $807.

What is the cheapest Wisconsin to Chicago flight route?

Fly from Milwaukee-Mitchell to Chicago O'Hare Intl for the best Wisconsin - Chicago flight prices

What cabin class options are available on Wisconsin to Chicago flights?

There are 4 cabin classes available to choose from on Wisconsin to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Wisconsin to Chicago flights?

No. A direct flight is the cheapest option for a flight between Wisconsin to Chicago.

What is the cheapest airline that flies from Wisconsin to Chicago?

Sun Country Air, Delta, and United Airlines are the most popular carriers operating from Wisconsin to Chicago

How many flights depart from Wisconsin to Chicago on average per day?

As of July 2025, there are 175 flights per day flying from Wisconsin to Chicago. The most common time of day flights depart is 10:00AM, with 45% of flights taking off in the afternoon.

How many flights depart from Wisconsin to Chicago on average per week?

1,225 flights are operational weekly from Wisconsin to Chicago as of July 2025. The most popular departure day for this route is Thu, with 22% of flights per week taking off on this day.

How long does it take to fly to Chicago?

Cheap Wisconsin to Chicago flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Wisconsin to Chicago

Best Price Found

Fastest flight time

Direct flights

Airports in Chicago

When did momondo last update prices for flights from Wisconsin to Chicago?

How many operators does momondo search for flights from Wisconsin to Chicago?

How old do you have to be to fly from Wisconsin to Chicago?

What documentation or ID do you need to fly to Chicago?

What is the most popular plane model from Wisconsin to Chicago?

Best airlines flying from Wisconsin to Chicago

Compare and see reviews for airlines that fly from Wisconsin to Chicago with momondo

Traveling to a place near Chicago?

Why use momondo?

Why should I use momondo to find a flight deal from Wisconsin to Chicago?

Can I find flights from Wisconsin to Chicago with flexible booking policies on momondo?

How can momondo help me find flights from Wisconsin to Chicago?

I’m not ready to book a flight from Wisconsin to Chicago right now. Can momondo alert me if prices change?

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago