Cheap flights To Southwest Side (CHI) from $31

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Cheap Flights to Southwest Side from $31 One Way, $62 Round Trip

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

Mon, May 19 - Sun, May 25
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$62 Roundtrip, just found
$62
Roundtrip
just found
Select Spirit Airlines flight, departing Mon, May 19 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sun, May 25, priced at $62 just found
Mon, Jun 2 - Tue, Jun 3
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$65 Roundtrip, found 5 hours ago
$65
Roundtrip
found 5 hours ago
Select Spirit Airlines flight, departing Mon, Jun 2 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Jun 3, priced at $65 found 5 hours ago
Thu, May 22 - Tue, May 27
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$69 Roundtrip, just found
$69
Roundtrip
just found
Select Spirit Airlines flight, departing Thu, May 22 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, May 27, priced at $69 just found
Wed, May 28 - Wed, Jun 4
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$71 Roundtrip, found 19 hours ago
$71
Roundtrip
found 19 hours ago
Select Spirit Airlines flight, departing Wed, May 28 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Jun 4, priced at $71 found 19 hours ago
Sat, May 31 - Tue, Jun 3
LGA
LaGuardia
ORD
O'Hare Intl.
$81 Roundtrip, just found
$81
Roundtrip
just found
Select Spirit Airlines flight, departing Sat, May 31 from LaGuardia to O'Hare Intl., returning Tue, Jun 3, priced at $81 just found
Wed, Aug 6 - Wed, Aug 6
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$83 Roundtrip, found 18 hours ago
$83
Roundtrip
found 18 hours ago
Select Frontier Airlines flight, departing Wed, Aug 6 from Dallas-Fort Worth Intl. to Midway Intl., returning Wed, Aug 6, priced at $83 found 18 hours ago
Wed, Jul 23 - Wed, Jul 23
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$83 Roundtrip, found 1 day ago
$83
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, Jul 23 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Wed, Jul 23, priced at $83 found 1 day ago
Tue, Jul 29 - Tue, Jul 29
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$83 Roundtrip, found 20 hours ago
$83
Roundtrip
found 20 hours ago
Select Frontier Airlines flight, departing Tue, Jul 29 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Jul 29, priced at $83 found 20 hours ago
Sat, Jul 12 - Tue, Jul 15
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$88 Roundtrip, found 14 hours ago
$88
Roundtrip
found 14 hours ago
Select Frontier Airlines flight, departing Sat, Jul 12 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Tue, Jul 15, priced at $88 found 14 hours ago
Wed, May 14 - Tue, May 27
LGA
LaGuardia
ORD
O'Hare Intl.
$139 Roundtrip, found 4 days ago
$139
Roundtrip
found 4 days ago
Select United flight, departing Wed, May 14 from LaGuardia to O'Hare Intl., returning Tue, May 27, priced at $139 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, JetBlue Airways, Southwest Airlines, United
Flight Price
$62
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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Southwest Side economy flight packages

Price found within the past 48 hours. Click for updated prices.
La Banque Hotel
4.0-star property

La Banque Hotel

Jun 5 - Jun 9

4 night stay

Atlanta (ATL) to Chicago (ORD)

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

Hotel Riu Plaza Chicago

Jun 19 - Jun 22

3 night stay

Atlanta (ATL) to Chicago (ORD)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
The Emily Hotel
4.0-star property

The Emily Hotel

Jun 5 - Jun 9

4 night stay

Atlanta (ATL) to Chicago (ORD)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
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Southwest Side 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 15 hours 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 15 hours 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 15 hours ago
Had an amazing stay beautiful hotel

Reviewed on Feb 16, 2025

Don't see what you're looking for?
See all available trips from Newark Liberty Intl. Airport to Southwest Side
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Southwest Side 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 15 hours 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 15 hours 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 15 hours 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 Southwest Side
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Southwest Side

When you plan to buy tickets for flights to Southwest Side, you don’t have to look any further than Orbitz! We offer bargain rates and low fares on thousands of flights.

Reliable Customer Service

Along with our low prices, Orbitz is well known for exceptional customer care. We make it simple to find the best Southwest Side flights for you. If you need to cancel your booking or change your flight plans, simply contact our Customer Service department to make any adjustments.

Bargain Tickets for Southwest Side Flights

Orbitz offers deeply discounted flights to Southwest Side, and we provide the resources to research your travel destination and plan your complete itinerary.

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Saving your frequent flyer miles for your flights to Southwest Side? You can use Orbitz to make your budget ticket reservation for all your flights and still earn points or miles on your frequent flyer program! Just enter your program account number while you’re booking your ticket to have your points added automatically, every time you book with Orbitz.

Convenient Travel Planning Services

If you like the ease of making your travel plans on the move, you’ll love the free Orbitz apps for iPhones, iPads, and Android devices. You can use these apps to review your travel reservations or make a change to your itinerary. Orbitz also offers additional travel assistance such as free mobile alerts that keep you up-to-date about sudden changes to your upcoming flights. You can also browse Orbitz easily on your smartphone by using the mobile version of the website to find budget Southwest Side flights.

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 $62 to $139 this week. Arriving from Atlanta (ATL)? The most affordable one-way fares were $31.
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.

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.