Cheap flights To Southwest Side (CHI) from $53

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Cheap Flights to Southwest Side from $53 One Way, $106 Round Trip

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

Sat, Sep 6 - Sat, Sep 13
LGA
LaGuardia
ORD
O'Hare Intl.
$106 Roundtrip, just found
$106
Roundtrip
just found
Select Spirit Airlines flight, departing Sat, Sep 6 from LaGuardia to O'Hare Intl., returning Sat, Sep 13, priced at $106 just found
Tue, Jul 22 - Tue, Jul 29
LGA
LaGuardia
ORD
O'Hare Intl.
$111 Roundtrip, found 15 hours ago
$111
Roundtrip
found 15 hours ago
Select Spirit Airlines flight, departing Tue, Jul 22 from LaGuardia to O'Hare Intl., returning Tue, Jul 29, priced at $111 found 15 hours ago
Thu, Jul 24 - Tue, Jul 29
LGA
LaGuardia
ORD
O'Hare Intl.
$115 Roundtrip, found 6 hours ago
$115
Roundtrip
found 6 hours ago
Select Spirit Airlines flight, departing Thu, Jul 24 from LaGuardia to O'Hare Intl., returning Tue, Jul 29, priced at $115 found 6 hours ago
Tue, Jul 22 - Tue, Jul 29
LGA
LaGuardia
ORD
O'Hare Intl.
$116 Roundtrip, found 7 hours ago
$116
Roundtrip
found 7 hours ago
Select Spirit Airlines flight, departing Tue, Jul 22 from LaGuardia to O'Hare Intl., returning Tue, Jul 29, priced at $116 found 7 hours ago
Thu, Sep 4 - Sat, Sep 6
LGA
LaGuardia
ORD
O'Hare Intl.
$118 Roundtrip, just found
$118
Roundtrip
just found
Select Spirit Airlines flight, departing Thu, Sep 4 from LaGuardia to O'Hare Intl., returning Sat, Sep 6, priced at $118 just found
Fri, Jul 18 - Tue, Jul 29
LGA
LaGuardia
ORD
O'Hare Intl.
$119 Roundtrip, found 2 days ago
$119
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Fri, Jul 18 from LaGuardia to O'Hare Intl., returning Tue, Jul 29, priced at $119 found 2 days ago
Sat, Jul 12 - Fri, Jul 25
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$119 Roundtrip, found 6 days ago
$119
Roundtrip
found 6 days ago
Select Spirit Airlines flight, departing Sat, Jul 12 from Los Angeles Intl. to O'Hare Intl., returning Fri, Jul 25, priced at $119 found 6 days ago
Sat, Nov 8 - Tue, Nov 11
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$120 Roundtrip, found 2 days ago
$120
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Sat, Nov 8 from Los Angeles Intl. to O'Hare Intl., returning Tue, Nov 11, priced at $120 found 2 days ago
Thu, Oct 23 - Sat, Oct 25
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$132 Roundtrip, found 4 hours ago
$132
Roundtrip
found 4 hours ago
Select Spirit Airlines flight, departing Thu, Oct 23 from Newark Liberty Intl. Airport to O'Hare Intl., returning Sat, Oct 25, priced at $132 found 4 hours ago
Sat, Aug 30 - Wed, Sep 3
JFK
John F. Kennedy Intl.
ORD
O'Hare Intl.
$137 Roundtrip, found 3 days ago
$137
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Sat, Aug 30 from John F. Kennedy Intl. to O'Hare Intl., returning Wed, Sep 3, priced at $137 found 3 days ago

Southwest Side Flight Information

Traveling To
Southwest Side
Destination Airport IATA Code
CHI
Number of Airlines Serving
Airlines
Spirit Airlines, Southwest Airlines, JetBlue Airways
Flight Price
$106
Earliest Departing Flight
Latest Departing Flight

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Southwest Side economy 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

Aug 17 - Aug 19

2 night stay

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

Spirit Airlines • Non-stop • Coach

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

United • Non-stop • Coach
Save 100% on your flight
per person
found 1 day ago
Chicago Athletic Association, a Hyatt Hotel
4.5-star property

Chicago Athletic Association, a Hyatt Hotel

Aug 6 - Aug 12

6 night stay

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

United • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
The Allegro Royal Sonesta Hotel Chicago Loop
4.0-star property

The Allegro Royal Sonesta Hotel Chicago Loop

Aug 6 - Aug 12

6 night stay

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

United • 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.
Swissotel - Chicago
4.5-star property

Swissotel - Chicago

8.8/10 Excellent! (2,274 reviews)

Aug 31 - Sep 4

4 night stay

New York (JFK) to Chicago (ORD)

Delta • Roundtrip • PremiumEconomy
Save 100% on your flight
per person
found 1 day ago
Clean and attentive staff

Reviewed on Jun 21, 2025

Park Hyatt Chicago
5.0-star property

Park Hyatt Chicago

9.6/10 Exceptional! (1,002 reviews)

Aug 31 - Sep 4

4 night stay

New York (JFK) to Chicago (ORD)

Delta • Roundtrip • PremiumEconomy
Save 100% on your flight
per person
found 1 day 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

Trump International Hotel & Tower Chicago
5.0-star property

Trump International Hotel & Tower Chicago

9.4/10 Exceptional! (1,623 reviews)

Aug 31 - Sep 4

4 night stay

New York (JFK) to Chicago (ORD)

Delta • Roundtrip • PremiumEconomy
Save 100% on your flight
per person
found 1 day ago
This is the nicest hotel that I have ever stayed at. Everything was perfect!

Reviewed on Jun 16, 2025

Don't see what you're looking for?
See all available trips from New York to Southwest Side
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Southwest Side first class flight packages

Price found within the past 48 hours. Click for updated prices.
Palmer House a Hilton Hotel
4.0-star property

Palmer House a Hilton Hotel

8.4/10 Very Good! (1,755 reviews)

Aug 14 - Aug 17

3 night stay

New York (JFK) to Chicago (ORD)

Delta • Non-stop roundtrip • FirstClass
per person
found 20 hours ago
Old school, nice and clean

Reviewed on Jun 21, 2025

Hilton Chicago/Magnificent Mile Suites
3.5-star property

Hilton Chicago/Magnificent Mile Suites

8.8/10 Excellent! (2,332 reviews)

Aug 14 - Aug 17

3 night stay

New York (JFK) to Chicago (ORD)

Delta • Non-stop roundtrip • FirstClass
per person
found 20 hours ago
Hard to located without sign took us 30 minutes to find hotel

Reviewed on Jun 29, 2025

Embassy Suites by Hilton Chicago Downtown River North
4.0-star property

Embassy Suites by Hilton Chicago Downtown River North

8.4/10 Very Good! (4,263 reviews)

Aug 14 - Aug 17

3 night stay

New York (JFK) to Chicago (ORD)

Delta • Non-stop roundtrip • FirstClass
per person
found 20 hours ago
It was a great location and staff was super friendly!

Reviewed on Jun 28, 2025

Don't see what you're looking for?
See all available trips from New York to Southwest Side
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Southwest Side

Start your search for cheap flights to Southwest Side on Orbitz. Orbitz is where you will discover guaranteed low prices on Southwest Side flights, as well as all of the following conveniences:

Travel Updates on Your Mobile Device

Orbitz offers cutting-edge mobile tools for your smartphone. Whether you own an iPhone or an Android phone, you can benefit from Orbitz’s flight status updates and even book your future Southwest Side flights. You can also review and reserve hotel rooms for when your Southwest Side flights land and see other special offers.

Low Prices Guaranteed on Flights to Southwest Side

Orbitz offers large discounts on a wide range of Southwest Side flights. Through our easy-to-use site, you can find, plan, and reserve your desired flights to Southwest Side while taking advantage of the lowest fares around.

Customer Care When You Need It

Orbitz is dedicated to making your flight booking experience as stress-free as possible. If you need to cancel your reservation, you can do so at your own convenience by going to the Orbitz website. If you need to change your flights to Southwest Side to another time or date, you can contact our customer service representatives by phone, and they help you make the flight adjustments you need.

Loyalty Program Participation Opportunities

Orbitz lets you add your loyalty or frequent flyer account numbers when you book qualifying flights to Southwest Side. So don’t worry about missing out on earning miles or points simply because you aren’t booking with the airline directly. You can save on your flights, and rack up miles too.

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 $106 to $137 this week. Arriving from New York (LGA)? The most affordable one-way fares were $53.
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.