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 9 - Sun, Oct 12
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 9 from Orlando Intl. to General Mitchell Intl., returning Sun, Oct 12, priced at $110 found 3 hours ago
Sat, Aug 30 - Sat, Sep 6
MCO
Orlando Intl.
MSN
Dane County Regional
$143 Roundtrip, just found
$143
Roundtrip
just found
Select Breeze Airways flight, departing Sat, Aug 30 from Orlando Intl. to Dane County Regional, returning Sat, Sep 6, priced at $143 just found
Thu, Dec 25 - Thu, Jan 1
MCO
Orlando Intl.
MKE
General Mitchell Intl.
$149 Roundtrip, found 2 hours ago
$149
Roundtrip
found 2 hours ago
Select Sun Country Airlines flight, departing Thu, Dec 25 from Orlando Intl. to General Mitchell Intl., returning Thu, Jan 1, priced at $149 found 2 hours ago
Tue, Oct 21 - Wed, Oct 22
BOS
Logan Intl.
MKE
General Mitchell Intl.
$157 Roundtrip, found 2 days ago
$157
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Tue, Oct 21 from Logan Intl. to General Mitchell Intl., returning Wed, Oct 22, priced at $157 found 2 days ago
Tue, Oct 21 - Wed, Oct 22
BOS
Logan Intl.
MKE
General Mitchell Intl.
$172 Roundtrip, found 2 days ago
$172
Roundtrip
found 2 days ago
Select United flight, departing Tue, Oct 21 from Logan Intl. to General Mitchell Intl., returning Wed, Oct 22, priced at $172 found 2 days ago
Tue, Oct 21 - Wed, Oct 22
BOS
Logan Intl.
MKE
General Mitchell Intl.
$177 Roundtrip, found 2 days ago
$177
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Tue, Oct 21 from Logan Intl. to General Mitchell Intl., returning Wed, Oct 22, priced at $177 found 2 days ago
Tue, Oct 21 - Wed, Oct 22
BOS
Logan Intl.
MKE
General Mitchell Intl.
$177 Roundtrip, found 2 days ago
$177
Roundtrip
found 2 days ago
Select American Airlines flight, departing Tue, Oct 21 from Logan Intl. to General Mitchell Intl., returning Wed, Oct 22, priced at $177 found 2 days ago
Wed, Aug 13 - Wed, Aug 20
BOS
Logan Intl.
MKE
General Mitchell Intl.
$180 Roundtrip, found 5 days ago
$180
Roundtrip
found 5 days ago
Select Delta flight, departing Wed, Aug 13 from Logan Intl. to General Mitchell Intl., returning Wed, Aug 20, priced at $180 found 5 days ago
Fri, Oct 31 - Mon, Nov 3
BOS
Logan Intl.
RFD
Greater Rockford
$225 Roundtrip, found 5 days ago
$225
Roundtrip
found 5 days ago
Select American Airlines flight, departing Fri, Oct 31 from Logan Intl. to Greater Rockford, returning Mon, Nov 3, priced at $225 found 5 days ago
Fri, Oct 31 - Mon, Nov 3
BOS
Logan Intl.
MSN
Dane County Regional
$229 Roundtrip, found 5 days ago
$229
Roundtrip
found 5 days ago
Select American Airlines flight, departing Fri, Oct 31 from Logan Intl. to Dane County Regional, returning Mon, Nov 3, priced at $229 found 5 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, JetBlue Airways, United, Southwest Airlines, American Airlines, Delta
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

Book Your Flight & Hotel Together & Save

Southern Wisconsin economy flight packages

Price found within the past 48 hours. Click for updated prices.
Harrah's Joliet Casino & Hotel
3.5-star property

Harrah's Joliet Casino & Hotel

Sep 4 - Sep 7

3 night stay

Los Angeles (LAX) to Chicago (CHI)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 11 hours ago
Arlo Chicago
4.0-star property

Arlo Chicago

Sep 11 - Sep 15

4 night stay

Newark Liberty Intl. Airport (EWR) to Chicago (ORD)

United • Coach

Chicago (ORD) to Newark Liberty Intl. Airport (EWR)

Spirit Airlines • Coach
Save 100% on your flight
per person
found 1 day ago
Trump International Hotel & Tower Chicago
5.0-star property

Trump International Hotel & Tower Chicago

Sep 5 - Sep 7

2 night stay

Newark Liberty Intl. Airport (EWR) to Chicago (ORD)

United • Coach

Chicago (ORD) to Newark Liberty Intl. Airport (EWR)

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

End your search for discount fares on flights to Southern Wisconsin. Orbitz has all the best prices on Southern Wisconsin flights. With Orbitz, you can expect:

Cheap Deals on Flights to Southern Wisconsin

We offer big discounts and last-minute savings on Southern Wisconsin flights. We make it easy for you to research, plan, and book your flight to Southern Wisconsin — all while offering great low fares. With guaranteed low prices and cutting-edge mobile tools, the perfect trip begins on Orbitz.

Travel Convenience on the Go

Get alerts, updates, or book your Southern Wisconsin flight or other flights wherever you are. Download our free apps for iPhone, Android, and iPad or visit our mobile site at m.orbitz.com to conveniently review or change your air travel plans. We can also send free alerts about your Southern Wisconsin flight to your email or mobile phone, so you get advance warning about potential disruptions and flight delays. Need to book a hotel with your Southern Wisconsin flight? Access exclusive, mobile-only deals via our mobile site and free apps – even on the same day.

Great Customer Care

We want to make your travel booking experience smooth and easy, from planning and researching Southern Wisconsin flights to the actual booking. If you want to cancel your flight to Southern Wisconsin, many tickets can be conveniently cancelled online. Contact our Customer Service to make changes to your air ticket.

Miles or Points Toward Frequent Flyer Programs

Much like booking with an airline directly, you can earn frequent flyer miles or points on qualified flights to Southern Wisconsin with Orbitz. When completing your booking, just fill in your frequent flyer number for the airline you are flying with or for one of its available partner airlines.

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 $229. 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.