Cheap flights To Southern Wisconsin (CHI) from $55

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Cheap Flights to Southern Wisconsin from $55 One Way, $110 Round Trip

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Thu, Oct 23 - Sun, Oct 26
MCO
Orlando Intl.
MKE
General Mitchell Intl.
$110 Roundtrip, found 3 hours ago
$110
Roundtrip
found 3 hours ago
Select Spirit Airlines flight, departing Thu, Oct 23 from Orlando Intl. to General Mitchell Intl., returning Sun, Oct 26, priced at $110 found 3 hours ago
Thu, Aug 28 - Sun, Aug 31
LAX
Los Angeles Intl.
MKE
General Mitchell Intl.
$132 Roundtrip, found 2 days ago
$132
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Thu, Aug 28 from Los Angeles Intl. to General Mitchell Intl., returning Sun, Aug 31, priced at $132 found 2 days ago
Sat, Sep 27 - Sat, Oct 4
MCO
Orlando Intl.
MSN
Dane County Regional
$142 Roundtrip, found 1 day ago
$142
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Sat, Sep 27 from Orlando Intl. to Dane County Regional, returning Sat, Oct 4, priced at $142 found 1 day ago
Thu, Dec 18 - Thu, Jan 1
MCO
Orlando Intl.
MKE
General Mitchell Intl.
$149 Roundtrip, found 1 day ago
$149
Roundtrip
found 1 day ago
Select Sun Country Airlines flight, departing Thu, Dec 18 from Orlando Intl. to General Mitchell Intl., returning Thu, Jan 1, priced at $149 found 1 day ago
Thu, Sep 4 - Thu, Sep 11
MCO
Orlando Intl.
MKE
General Mitchell Intl.
$183 Roundtrip, found 2 hours ago
$183
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Thu, Sep 4 from Orlando Intl. to General Mitchell Intl., returning Thu, Sep 11, priced at $183 found 2 hours ago
Thu, Sep 4 - Tue, Sep 9
MCO
Orlando Intl.
MKE
General Mitchell Intl.
$199 Roundtrip, found 2 days ago
$199
Roundtrip
found 2 days ago
Select Delta flight, departing Thu, Sep 4 from Orlando Intl. to General Mitchell Intl., returning Tue, Sep 9, priced at $199 found 2 days ago
Sun, Sep 21 - Mon, Sep 22
MCO
Orlando Intl.
MKE
General Mitchell Intl.
$202 Roundtrip, found 2 days ago
$202
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Sun, Sep 21 from Orlando Intl. to General Mitchell Intl., returning Mon, Sep 22, priced at $202 found 2 days ago
Sat, Aug 16 - Sat, Aug 30
LAX
Los Angeles Intl.
MSN
Dane County Regional
$205 Roundtrip, found 5 days ago
$205
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Sat, Aug 16 from Los Angeles Intl. to Dane County Regional, returning Sat, Aug 30, priced at $205 found 5 days ago
Mon, Sep 8 - Thu, Sep 11
LAX
Los Angeles Intl.
MKE
General Mitchell Intl.
$210 Roundtrip, found 1 day ago
$210
Roundtrip
found 1 day ago
Select Alaska Airlines flight, departing Mon, Sep 8 from Los Angeles Intl. to General Mitchell Intl., returning Thu, Sep 11, priced at $210 found 1 day ago
Sat, Aug 30 - Tue, Sep 2
MCO
Orlando Intl.
MSN
Dane County Regional
$237 Roundtrip, found 2 days ago
$237
Roundtrip
found 2 days ago
Select United flight, departing Sat, Aug 30 from Orlando Intl. to Dane County Regional, returning Tue, Sep 2, priced at $237 found 2 days ago

Southern Wisconsin Flight Information

Traveling To
Southern Wisconsin
Destination Airport IATA Code
CHI
Number of Airlines Serving
Airlines
Spirit Airlines, Sun Country Airlines, Breeze Airways, Southwest Airlines, American Airlines, Delta, Alaska Airlines, United
Flight Price
$110
Earliest Departing Flight
Latest Departing Flight

Flights Review

Mar 10, 2018

Great overall service. Smooth landing. Plane was even early.

A verified traveler
Denver to Chicago · United

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Southern Wisconsin economy flight packages

Price found within the past 48 hours. Click for updated prices.
Illinois Beach Hotel
2.0-star property

Illinois Beach Hotel

Sep 17 - Sep 20

3 night stay

Fort Lauderdale (FLL) to Chicago (ORD)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
Dorothy's
3.0-star property

Dorothy's

Sep 29 - Oct 3

4 night stay

New Orleans (MSY) to Chicago (ORD)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
The Stella Hotel & Ballroom
3.5-star property

The Stella Hotel & Ballroom

Sep 17 - Sep 20

3 night stay

Fort Lauderdale (FLL) to Chicago (CHI)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
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Southern Wisconsin premium economy flight packages

Price found within the past 48 hours. Click for updated prices.
Fairmont Chicago at Millennium Park
4.5-star property

Fairmont Chicago at Millennium Park

8.6/10 Excellent! (1,816 reviews)

Sep 19 - Sep 21

2 night stay

Los Angeles (LAX) to Chicago (ORD)

Delta • Non-stop roundtrip • PremiumEconomy
per person
found 23 hours ago
The rooms was smelly! It is more like a 3 .5 stars hotel. Towel and bedsheet had roles.

Reviewed on Jul 30, 2025

Trump International Hotel & Tower Chicago
5.0-star property

Trump International Hotel & Tower Chicago

9.4/10 Exceptional! (1,659 reviews)

Sep 19 - Sep 21

2 night stay

Los Angeles (LAX) to Chicago (ORD)

Delta • Non-stop roundtrip • PremiumEconomy
per person
found 23 hours ago
This is the nicest hotel that I have ever stayed at. Everything was perfect!

Reviewed on Jun 16, 2025

Park Hyatt Chicago
5.0-star property

Park Hyatt Chicago

9.6/10 Exceptional! (1,000 reviews)

Sep 19 - Sep 21

2 night stay

Los Angeles (LAX) to Chicago (ORD)

Delta • Non-stop roundtrip • PremiumEconomy
per person
found 23 hours ago
From the moment you walk into their lobby at the hotel, you enter a place of calm and relaxation. We stayed in a room with the Water Tower view, and if you have that as the option, take it. It was a beautiful sight to see waking up every morning. This hotel like their other properties are in a class of their own.

Reviewed on Sep 13, 2024

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Southern Wisconsin first class flight packages

Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
5.0-star property

Trump International Hotel & Tower Chicago

9.4/10 Exceptional! (1,659 reviews)

Sep 11 - Sep 14

3 night stay

Los Angeles (LAX) to Chicago (ORD)

American Airlines • FirstClass

Chicago (ORD) to Los Angeles (LAX)

United • FirstClass
per person
found 23 hours ago
This is the nicest hotel that I have ever stayed at. Everything was perfect!

Reviewed on Jun 16, 2025

Park Hyatt Chicago
5.0-star property

Park Hyatt Chicago

9.6/10 Exceptional! (1,000 reviews)

Sep 11 - Sep 14

3 night stay

Los Angeles (LAX) to Chicago (ORD)

American Airlines • FirstClass

Chicago (ORD) to Los Angeles (LAX)

United • FirstClass
per person
found 23 hours ago
From the moment you walk into their lobby at the hotel, you enter a place of calm and relaxation. We stayed in a room with the Water Tower view, and if you have that as the option, take it. It was a beautiful sight to see waking up every morning. This hotel like their other properties are in a class of their own.

Reviewed on Sep 13, 2024

Nobu Hotel Chicago
5.0-star property

Nobu Hotel Chicago

9.4/10 Exceptional! (704 reviews)

Sep 11 - Sep 14

3 night stay

Los Angeles (LAX) to Chicago (ORD)

American Airlines • FirstClass

Chicago (ORD) to Los Angeles (LAX)

United • FirstClass
per person
found 23 hours ago
Best hotel I ever been in

Reviewed on Jul 16, 2024

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Southern Wisconsin

Why search for low cost fares on your flights to Southern Wisconsin when Orbitz offers the guaranteed lowest prices on foreign and domestic flights? When you travel with Orbitz you can benefit from:

Bargain Flights to Southern Wisconsin

Orbitz offers massive discounts and substantial last-minute savings on your Southern Wisconsin flights. Orbitz ensures that you can find, plan and reserve your flights any destination with ease, all while enjoying the guaranteed lowest prices available anywhere.

Cutting-Edge Mobile Tools to Keep You In The Know

Orbitz sends you free alerts and updates on your Southern Wisconsin flight wherever you are in the world. Once you have downloaded the free app for your iPhone, Android, or iPad, you can review or alter any travel plans that you have made or even book a future flight for business or pleasure. If you need to reserve a hotel room when booking your flight, you will find exclusive deals on our mobile site.

Frequent Flyer Program Enrolment

Orbitz finds you the lowest fares, but you can still add your miles to your frequent flyer program to earn miles or points on selected flights to Southern Wisconsin. When making your booking, reference your frequent flyer number to receive discounts in the future.

Outstanding Customer Service

Orbitz values your business and wants to ensure that all of your flights are as easy as possible to book. If you have booked a flight to Southern Wisconsin but need to cancel it, you may be able to do so online. If you have any questions or need help, the dedicated Orbitz customer service team is always standing by.

Frequently asked questions

Which airlines fly to Southern Wisconsin?
With 20 airlines flying to General Mitchell Intl. Airport (MKE), you'll be making your way around Southern Wisconsin in no time at all. Picking a flight that suits your itinerary is simple. Compare the available fares from these top air carriers and prepare for a smooth landing at General Mitchell Intl. Airport (MKE):

  • Delta - 277 flights to Southern Wisconsin per month
  • Southwest Airlines - 248 flights to Southern Wisconsin per month
  • United Airlines - 239 flights to Southern Wisconsin per month

How much is a flight to Southern Wisconsin?
Loads of fantastic deals were on offer this week, with return flights to Southern Wisconsin fluctuating from $110 to $237. But it was travelers arriving in from Orlando (MCO) who bagged the really big bargains. One-way tickets to Southern Wisconsin fell to a low $55.
How to book the cheapest flight to Southern Wisconsin?
With some of the biggest and best flight deals around, you'll always jet for less with Orbitz. The following handy hints will help you score cheap flights to Southern Wisconsin — and leave you with more money to play with:

  • Consider departing from or arriving at nearby airports to save on your airfare. Enter your preferred departure and arrival airports in the form fields, then choose the 'Nearby airports' function below. It will list any available options.
  • If you're flexible with your travel itinerary, click on the 'Show flexible dates' option. It'll show the flight deals for the days either side of your chosen departure. Airfares often vary depending on what day it is.
  • Select 'Show options' to narrow down your search results. You can pick your preferred seating class and airline here. Under 'Sort & Filter' to the left, you can even specify whether you'd like to fly in the morning, afternoon or evening.
  • Once you've figured out your travel dates, don't wait to book. Prices normally become more expensive as the departure date gets closer.
  • Think about combining your flights, hotels and car rentals into a package with Orbitz to stretch your budget even further.
  • Don't fly during the busy season if you can. By steering clear of school vacations and summer, you can make amazing savings on your airfare.

What is the best time to book a flight to Southern Wisconsin?
Catch a bargain and secure your seats to Southern Wisconsin in January. If you've missed this month, don't stress. February and August often have low airfares as well. Make sure you don't snooze on a sale — cheap flights emerge and disappear in the click of a mouse!
What day of the week is the cheapest to book a flight to Southern Wisconsin?
If you're after cheap fares to Southern Wisconsin, the best days of the week to book are Tuesdays, Wednesdays and Saturdays. With Orbitz (and some good timing!), an unbeatable flight deal will be all yours.
What is the cheapest day of the week to fly to Southern Wisconsin?
Look into departing early in the week if you want to score cheap flights to Southern Wisconsin. Orbitz data from 2020 indicates Monday is generally the most affordable day to take off, followed by Tuesday. Saturday was found to have the highest ticket prices. This is probably because most passengers prefer to begin their escape when the working week is over.
What is the cheapest month to fly to Southern Wisconsin?
If you have some flexibility with your travel plans, think about jetting off sometime in August. Orbitz data has found that this is generally the best month to travel if you're after cheap flights to Southern Wisconsin. As you might expect, airfares get pricier in the busy month of June and flights get snapped up fast.
Which airlines allow free cancellation?
Flexible travel is more important than ever, that's why Orbitz lets you search for airlines that won't penalize you for amendments to your reservation. Enter your departure and arrival points, then click on "Filter by flexible change policies." We'll show you options that include free cancellation within 24 hours of booking and no change fees.
What do I need for the flight to Southern Wisconsin?
Flying can be fun with a little pre-planning! Make your trip a hassle-free one with these handy tips:

  • Before you step on board the plane, you'll need to show some type of government-issued ID, like your passport. You'll also need your boarding pass. If you're traveling with the kids, check with your airline about which documents they may need.
  • To keep you entertained on the short hop to Southern Wisconsin, download some new music or stock up the audiobook library on your phone. Food can also be a nice distraction while in the air, so take some snacks.
  • It can get cold on the plane. If you'd prefer not to shiver your way through the flight, dress in layers.

How do I get cheap first-class/business deals to Southern Wisconsin?
Smart travelers are pros at finding first or business-class flights to Southern Wisconsin that don't cost an arm and a leg. Take a leaf out of their book with these handy hints:

  • Flexibility is everything. By being open to different travel dates, you'll have better odds of landing a great deal on your airfares.
  • Low-cost airlines offer business-class seating at a fraction of the normal price. Give the full-service carriers a miss and look into these cheaper options.
  • Make the most of your airline's rewards program and use points to upgrade your seat. Alternatively, you can try bidding for an upgrade in an online auction.

What is the best time to go to Southern Wisconsin?
There's no right or wrong time to experience Southern Wisconsin, though June, July and August are the busiest months. Like most of the Northern Hemisphere, summertime kicks off June 20. If you'd prefer to spend your days in a light shirt than a thick winter coat, this time of year may be perfect for you. Expect average daily highs of 75 ºF and nightly lows around 60 ºF.

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Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.