Cheap flights To Southwest Side (CHI) from $27

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Cheap Flights to Southwest Side from $27 One Way, $54 Round Trip

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

Wed, Feb 18 - Wed, Feb 25
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$54 Roundtrip, found 1 hour ago
$54
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Wed, Feb 18 from Newark Liberty Intl. Airport to O'Hare Intl., returning Wed, Feb 25, priced at $54 found 1 hour ago
Sat, Feb 28 - Wed, Mar 4
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$54 Roundtrip, found 3 hours ago
$54
Roundtrip
found 3 hours ago
Select Spirit Airlines flight, departing Sat, Feb 28 from Newark Liberty Intl. Airport to O'Hare Intl., returning Wed, Mar 4, priced at $54 found 3 hours ago
Tue, Feb 17 - Sat, Feb 28
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$56 Roundtrip, found 1 hour ago
$56
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Tue, Feb 17 from Newark Liberty Intl. Airport to O'Hare Intl., returning Sat, Feb 28, priced at $56 found 1 hour ago
Fri, Apr 24 - Wed, May 6
EWR
Newark Liberty Intl. Airport
MDW
Midway Intl.
$56 Roundtrip, found 3 hours ago
$56
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Fri, Apr 24 from Newark Liberty Intl. Airport to Midway Intl., returning Wed, May 6, priced at $56 found 3 hours ago
Fri, Feb 20 - Mon, Feb 23
JFK
John F. Kennedy Intl.
ORD
O'Hare Intl.
$57 Roundtrip, just found
$57
Roundtrip
just found
Select Frontier Airlines flight, departing Fri, Feb 20 from John F. Kennedy Intl. to O'Hare Intl., returning Mon, Feb 23, priced at $57 just found
Thu, Feb 26 - Mon, Mar 2
JFK
John F. Kennedy Intl.
ORD
O'Hare Intl.
$57 Roundtrip, found 1 hour ago
$57
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Thu, Feb 26 from John F. Kennedy Intl. to O'Hare Intl., returning Mon, Mar 2, priced at $57 found 1 hour ago
Thu, Feb 19 - Fri, Feb 27
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$58 Roundtrip, found 6 days ago
$58
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Thu, Feb 19 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Fri, Feb 27, priced at $58 found 6 days ago
Fri, Feb 27 - Mon, Mar 2
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$58 Roundtrip, found 5 hours ago
$58
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Fri, Feb 27 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Mon, Mar 2, priced at $58 found 5 hours ago
Wed, Feb 11 - Wed, Feb 11
LGA
LaGuardia
ORD
O'Hare Intl.
$63 Roundtrip, found 4 days ago
$63
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Wed, Feb 11 from LaGuardia to O'Hare Intl., returning Wed, Feb 11, priced at $63 found 4 days ago
Wed, Feb 25 - Wed, Feb 25
JFK
John F. Kennedy Intl.
ORD
O'Hare Intl.
$114 Roundtrip, found 4 days ago
$114
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Wed, Feb 25 from John F. Kennedy Intl. to O'Hare Intl., returning Wed, Feb 25, priced at $114 found 4 days ago

Southwest Side Flight Information

Traveling To
Southwest Side
Destination Airport IATA Code
CHI
Number of Airlines Serving
Airlines
Spirit Airlines, Frontier Airlines, Southwest Airlines, American Airlines, JetBlue Airways
Flight Price
$54
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

Southwest Side economy flight packages

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

Mar 19 - Mar 22

3 night stay

Dallas (DAL) to Chicago (ORD)

Southwest Airlines • Coach

Chicago (ORD) to Dallas (DAL)

Spirit Airlines • Coach
Price was $704, price is now $493 per person
$493
per person
found 1 day ago
Harrah's Joliet Casino & Hotel - A Caesars Rewards Destination
3.5-star property

Harrah's Joliet Casino & Hotel - A Caesars Rewards Destination

Feb 26 - Mar 1

3 night stay

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

American Airlines • Coach

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

United • Coach
Price was $812, price is now $576 per person
$576
per person
found 4 hours ago
Trump International Hotel & Tower Chicago
5.0-star property

Trump International Hotel & Tower Chicago

Mar 12 - Mar 16

4 night stay

Dallas (DAL) to Chicago (ORD)

Southwest Airlines • Coach

Chicago (ORD) to Dallas (DAL)

Frontier Airlines • Coach
Save 100% on your flight
Price was $1,401, price is now $1,002 per person
$1,002
per person
found 1 day ago
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Southwest Side

Reach your destination without breaking your budget by booking your flights to Southwest Side using Orbitz. We offer access to all of the best discounts on airfare, travel accommodations and even car rentals. Planning your trip and saving money are easier with Orbitz.

Get Discount Rates On Your Southwest Side Flight

Whether planning ahead or deciding to book your trip at the last minute, Orbitz will provide the lowest rates on Southwest Side flights. Using our free mobile phone apps will make you privy to a number of discounts that are unique to mobile phone users. These are perfect for harried travelers who want to find deals that they can qualify for on the same day.

Make Orbitz Your Official Travel Planner

Orbitz can be used for much more than comparing and booking a discount flight to Southwest Side. We also offer a variety of resources for securing the ideal travel accommodations while staying on budget. Travel tips, hotel reviews, customized suggestions and even detailed images can all be accessed through your mobile phone.

Build A Comprehensive Travel Itinerary

In addition to booking a low cost flight to Southwest Side, you can learn about the best places to visit, the best hotels to stay in and the preferred times for traveling. When you use Orbitz mobile phone apps you can also share your travel itineraries with friends and family members, all with just a few quick taps.

Using Orbitz to secure your Southwest Side flights can save you money and time. Perfect for both the early travel planner and the last minute journey: Orbitz offers phenomenal customer service and unbeatable convenience.

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Frequently asked questions

Which airlines fly to Southwest Side?
With 20 airlines waiting to spirit you away to Southwest Side, finding the perfect flight will be a piece of cake. Reserve your fare with one of these top carriers that jet into O'Hare Intl. Airport (ORD):

  • United Airlines - 612 flights to Southwest Side per month
  • American Airlines - 339 flights to Southwest Side per month
  • Air Canada - 190 flights to Southwest Side per month

What is the best airport to fly to in Southwest Side?
There's one primary entry point for this region — O'Hare Intl. Airport (ORD). Book your airfares for this popular gateway and see all that Southwest Side has to offer.
How much is a flight to Southwest Side?
Travelers from near and far picked up round-trip flight bargains ranging from $54 to $114 this week. Arriving from New York (EWR)? The most affordable one-way fares were $27.
How to book the cheapest flight to Southwest Side?
Using Orbitz, you'll find some of the most incredible flight deals around from a big selection of airlines. But if you want to increase your likelihood of nabbing cheap flights to Southwest Side, here are some tips to bear in mind:

  • Depending on where you're departing from, choose the 'Nearby airports' function (located under the departure and arrival form fields). In some cases, other departure points will have cheaper fares.
  • If your plans aren't written in stone, click on the 'Show flexible dates' link to scan the flight deals for a selection of departure dates. You may find an amazing fare.
  • You can also hit the 'Show options' function to filter results for your preferred airline, seating class, and nonstop and refundable flights. Under 'Sort & Filter' to the left, you can even choose the time of day you'd prefer to fly.
  • If you've worked out your travel dates, get booking. Airfares normally get dearer as the departure date gets closer.
  • Save loads on your vacation by combining your flights, hotels and car rentals into one convenient package deal. Your budget will thank you for it.
  • Don't travel during the busy season if you can. By steering clear of summer and school vacations, you can save a significant amount on your airfare.

How long is a flight to Southwest Side?
The USA is big, so that depends on where you're departing from. To make things easy, we've chosen some of the top routes to Southwest Side and worked out their average flight times:

  • New York, NY (LGA-LaGuardia) to O'Hare Intl. Airport (ORD) - 2 hours and 40 minutes
  • Boston, MA (BOS-Logan Intl.) to O'Hare Intl. Airport (ORD) - 2 hours and 51 minutes
  • Washington, DC (DCA-Ronald Reagan Washington National) to O'Hare Intl. Airport (ORD) - 2 hours and 13 minutes

What is the best time to book a flight to Southwest Side?
Book in January, February or August for the lowest airfares to Southwest Side. Once you've found a bargain, buy it — cheap flights tend to appear and then vanish in the click of a mouse.
What day of the week is the cheapest to book a flight to Southwest Side?
You can get a great flight deal by making a booking on a Tuesday, Wednesday or Saturday. These are typically the best days to land cheap airfares to Southwest Side.
What is the cheapest day of the week to fly to Southwest Side?
According to Orbitz data from 2020, Monday tends to be the best day to nab cheap flights to Southwest Side. Tuesday also offers wallet-friendly airfares, whereas Saturday has the highest ticket prices. Although leaving at the weekend can be more suitable, you'll have more money in your pocket to play with if you set off at the start of the week.
What is the cheapest month to fly to Southwest Side?
Travel sometime in August if you're on a tight budget. Orbitz data shows that this is generally the best month for cheap flights to Southwest Side. June is when ticket prices hit their peak.
Which airlines allow free cancellation?
When you search for flights on Orbitz, choose "Filter by flexible change policies." This filter will show you all the airlines offering free cancellation and no change fees. That means you can relax knowing that if your travel dates change, your ticket can too.
What do I need for the flight to Southwest Side?
The key to a stress-free flight is preparation. Listed below are some tips to help you get ready for departure:

  • Your travel documents are the most important things you'll need to take with you on your flight. To avoid any confusion when checking in, make sure that the information displayed on your ticket is the same as on your government-issued photo ID.
  • Take some activities to keep you entertained on your trip to Southwest Side. Magazines and electronic gadgets like tablets and e-readers should do the trick. Make sure you take a bottle of water with you as well. Even on short flights, it's important to keep well-hydrated.
  • Even if you're traveling when it's 90 degrees outside, carry a warm top or scarf on board with you. Cabins can get quite chilly!

How many direct flights are there to Southwest Side?
With approximately 2,332 direct flights each month, you'll be jetting straight into Southwest Side and beginning an exciting new adventure in no time. Some of the airlines that fly nonstop to Southwest Side include United Airlines, American Airlines and Delta Air Lines. Southwest Airlines, Spirit Airlines and Air Canada are some other reliable options.
How do I get cheap first-class/business deals to Southwest Side?
There are ways of booking first or business-class fares to Southwest Side that won't burn through your budget. Grab a seat in the pointy end of the plane for less with these practical tips:

  • Be flexible with your travel dates and wait for big sales on business or first-class airfares.
  • Low-cost airlines offer business-class seating at a fraction of the normal price. Ditch the full-service carriers and go with one of these cheaper options.
  • Bid for an upgrade in online auctions or upgrade your fare with points earned through loyalty programs.

What is the best time to go to Southwest Side?
Anytime is a fantastic time to experience Southwest Side, but March, May and June are the liveliest months. Like most of the Northern Hemisphere, summertime starts June 20. If you'd like to hang out in a light shirt than a winter coat, this time of the year would be perfect for you. Expect average daytime highs of 80 ºF and nighttime lows around 65 ºF.

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.