Cheap flights To Southern Wisconsin (CHI) from $50

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Cheap Flights to Southern Wisconsin from $50 One Way, $99 Round Trip

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

Tue, Jun 3 - Wed, Jun 4
MCO
Orlando Intl.
MKE
General Mitchell Intl.
$99 Roundtrip, found 6 hours ago
$99
Roundtrip
found 6 hours ago
Select Spirit Airlines flight, departing Tue, Jun 3 from Orlando Intl. to General Mitchell Intl., returning Wed, Jun 4, priced at $99 found 6 hours ago
Wed, May 21 - Wed, May 28
MCO
Orlando Intl.
MKE
General Mitchell Intl.
$102 Roundtrip, found 1 day ago
$102
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Wed, May 21 from Orlando Intl. to General Mitchell Intl., returning Wed, May 28, priced at $102 found 1 day ago
Wed, Jun 4 - Tue, Jun 10
MCO
Orlando Intl.
MKE
General Mitchell Intl.
$108 Roundtrip, found 6 hours ago
$108
Roundtrip
found 6 hours ago
Select Spirit Airlines flight, departing Wed, Jun 4 from Orlando Intl. to General Mitchell Intl., returning Tue, Jun 10, priced at $108 found 6 hours ago
Tue, May 27 - Sun, Jun 1
MCO
Orlando Intl.
MKE
General Mitchell Intl.
$110 Roundtrip, just found
$110
Roundtrip
just found
Select Spirit Airlines flight, departing Tue, May 27 from Orlando Intl. to General Mitchell Intl., returning Sun, Jun 1, priced at $110 just found
Wed, Sep 3 - Wed, Sep 10
MCO
Orlando Intl.
MSN
Dane County Regional
$142 Roundtrip, found 2 hours ago
$142
Roundtrip
found 2 hours ago
Select Breeze Airways flight, departing Wed, Sep 3 from Orlando Intl. to Dane County Regional, returning Wed, Sep 10, priced at $142 found 2 hours ago
Mon, Jun 2 - Tue, Jun 3
EWR
Newark Liberty Intl. Airport
MKE
General Mitchell Intl.
$170 Roundtrip, just found
$170
Roundtrip
just found
Select Spirit Airlines flight, departing Mon, Jun 2 from Newark Liberty Intl. Airport to General Mitchell Intl., returning Tue, Jun 3, priced at $170 just found
Thu, May 29 - Fri, May 30
EWR
Newark Liberty Intl. Airport
GRB
Austin Straubel Intl.
$199 Roundtrip, found 3 days ago
$199
Roundtrip
found 3 days ago
Select Delta flight, departing Thu, May 29 from Newark Liberty Intl. Airport to Austin Straubel Intl., returning Fri, May 30, priced at $199 found 3 days ago
Mon, Jul 7 - Sat, Jul 12
EWR
Newark Liberty Intl. Airport
MKE
General Mitchell Intl.
$209 Roundtrip, found 7 hours ago
$209
Roundtrip
found 7 hours ago
Select United flight, departing Mon, Jul 7 from Newark Liberty Intl. Airport to General Mitchell Intl., returning Sat, Jul 12, priced at $209 found 7 hours ago
Thu, May 29 - Mon, Jun 2
MCO
Orlando Intl.
MKE
General Mitchell Intl.
$214 Roundtrip, found 2 days ago
$214
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Thu, May 29 from Orlando Intl. to General Mitchell Intl., returning Mon, Jun 2, priced at $214 found 2 days ago
Wed, Jul 2 - Sat, Jul 5
MCO
Orlando Intl.
GRB
Austin Straubel Intl.
$217 Roundtrip, found 4 days ago
$217
Roundtrip
found 4 days ago
Select Delta flight, departing Wed, Jul 2 from Orlando Intl. to Austin Straubel Intl., returning Sat, Jul 5, priced at $217 found 4 days ago

Southern Wisconsin Flight Information

Traveling To
Southern Wisconsin
Destination Airport IATA Code
CHI
Number of Airlines Serving
Airlines
Spirit Airlines, Breeze Airways, American Airlines, United, Delta, Frontier Airlines
Flight Price
$99
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.
Chalet Motel Mequon
2.5-star property

Chalet Motel Mequon

Jun 28 - Jul 4

6 night stay

Newark Liberty Intl. Airport (EWR) to Milwaukee (MKE)

United • Roundtrip • Coach
per person
found 9 hours ago
Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

Jun 5 - Jun 10

5 night stay

Atlanta (ATL) to Chicago (ORD)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
La Banque Hotel
4.0-star property

La Banque Hotel

Jun 25 - Jun 29

4 night stay

Atlanta (ATL) to Chicago (ORD)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 17 hours ago
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Southern Wisconsin premium economy flight packages

Price found within the past 48 hours. Click for updated prices.
Hilton Chicago/Magnificent Mile Suites
3.5-star property

Hilton Chicago/Magnificent Mile Suites

8.8/10 Excellent! (2,064 reviews)

Jun 18 - Jun 22

4 night stay

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

Delta • Non-stop • PremiumEconomy

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

United • Non-stop • PremiumEconomy
per person
found 1 day ago
We had a great stay and would definitely return! We liked the location—everything we needed was close by, and we felt completely safe traveling as a group of women with a child. The hotel was within walking distance to fabulous shopping and dining, which made our trip extra enjoyable. For anyone planning to explore beyond the immediate area, we highly recommend getting a bus or “L” pass. Public transportation was easy to navigate and made getting around the city a breeze. One of the highlights of our stay was the incredibly kind and welcoming bellman (we regret not getting his name!). He went out of his way to make us feel at home, and that warm hospitality really stood out. The only downside was the sleeper sofa—the mattress could definitely use an upgrade for better comfort. Overall, we had a great experience and would recommend this hotel to others.

Reviewed on Apr 24, 2025

Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

9.4/10 Exceptional! (1,605 reviews)

Jun 18 - Jun 22

4 night stay

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

Delta • Non-stop • PremiumEconomy

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

United • Non-stop • PremiumEconomy
Save 100% on your flight
per person
found 1 day ago
Our second time. Here, highly recommended

Reviewed on Mar 3, 2025

Swissotel - Chicago
4.5-star property

Swissotel - Chicago

8.8/10 Excellent! (1,988 reviews)

Jun 18 - Jun 22

4 night stay

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

Delta • Non-stop • PremiumEconomy

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

United • Non-stop • PremiumEconomy
per person
found 1 day ago
Had an amazing stay beautiful hotel

Reviewed on Feb 16, 2025

Don't see what you're looking for?
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Southern Wisconsin first class flight packages

Price found within the past 48 hours. Click for updated prices.
Hilton Chicago/Magnificent Mile Suites
3.5-star property

Hilton Chicago/Magnificent Mile Suites

8.8/10 Excellent! (2,064 reviews)

Jun 18 - Jun 23

5 night stay

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

Delta • Non-stop • FirstClass

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

American Airlines • Non-stop • FirstClass
per person
found 1 day ago
We had a great stay and would definitely return! We liked the location—everything we needed was close by, and we felt completely safe traveling as a group of women with a child. The hotel was within walking distance to fabulous shopping and dining, which made our trip extra enjoyable. For anyone planning to explore beyond the immediate area, we highly recommend getting a bus or “L” pass. Public transportation was easy to navigate and made getting around the city a breeze. One of the highlights of our stay was the incredibly kind and welcoming bellman (we regret not getting his name!). He went out of his way to make us feel at home, and that warm hospitality really stood out. The only downside was the sleeper sofa—the mattress could definitely use an upgrade for better comfort. Overall, we had a great experience and would recommend this hotel to others.

Reviewed on Apr 24, 2025

Swissotel - Chicago
4.5-star property

Swissotel - Chicago

8.8/10 Excellent! (1,988 reviews)

Jun 18 - Jun 23

5 night stay

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

Delta • Non-stop • FirstClass

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

American Airlines • Non-stop • FirstClass
Save 100% on your flight
per person
found 1 day ago
Had an amazing stay beautiful hotel

Reviewed on Feb 16, 2025

Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

9.4/10 Exceptional! (1,605 reviews)

Jun 18 - Jun 23

5 night stay

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

Delta • Non-stop • FirstClass

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

American Airlines • Non-stop • FirstClass
Save 100% on your flight
per person
found 1 day ago
Our second time. Here, highly recommended

Reviewed on Mar 3, 2025

Don't see what you're looking for?
See all available trips from Newark Liberty Intl. Airport to Southern Wisconsin
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Southern Wisconsin

Traveling to Southern Wisconsin and need a cheap flight? Orbitz has great deals on flights to Southern Wisconsin right now. Plus, we offer big discounts on hotel rooms and car rentals for a great money-saving trip.

Find Low Cost Flights to Southern Wisconsin Quickly and Hassle-Free

There are many Internet sites that promise cheap Southern Wisconsin flights, but a busy, bargain-minded trip planner needs more than just budget air tickets. Not only does Orbitz offer the best deals for domestic and international air fare, but we also provide the resources and tools to help you plan your flights to Southern Wisconsin, book your lodging, and look up key attractions in Southern Wisconsin. Our easy search tools and guaranteed low prices let you budget your time and your money so you have more of both to spend on your vacation.

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You no longer need to be sitting at your computer to find amazing Orbitz sales for flights to Southern Wisconsin now we offer cutting-edge mobile tools for many Android and iOS gadgets. These free apps allow you to run a search for discount air fare, look for special vacation packages, or check on your booked Southern Wisconsin flights from any location. Some special deals are only available for mobile customers, so be sure to take advantage of these free downloads today.

Orbitz Customers Are Truly #1

Orbitz takes pride in providing the best customer experience possible, and that effort doesn't end with discount flights to Southern Wisconsin or user-friendly mobile apps and web tools. Orbitz Customer Service is always ready to answer questions and help you with booking, planning, or canceling your Southern Wisconsin flights. When you need us, we’re here for you!

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 $99 to $217. 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 $50.
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.

Nearby

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.