Cheap flights To Southwest Side (CHI) from $32

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Cheap Flights to Southwest Side from $32 One Way, $72 Round Trip

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

Tue, Jul 29 - Wed, Jul 30
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$72 Roundtrip, just found
$72
Roundtrip
just found
Select Spirit Airlines flight, departing Tue, Jul 29 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Jul 30, priced at $72 just found
Tue, Jul 22 - Tue, Jul 22
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$76 Roundtrip, just found
$76
Roundtrip
just found
Select Spirit Airlines flight, departing Tue, Jul 22 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Jul 22, priced at $76 just found
Sat, Jul 19 - Tue, Jul 29
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$82 Roundtrip, found 6 days ago
$82
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Sat, Jul 19 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Tue, Jul 29, priced at $82 found 6 days ago
Sat, Sep 6 - Sat, Sep 6
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$83 Roundtrip, found 4 days ago
$83
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Sat, Sep 6 from Dallas-Fort Worth Intl. to Midway Intl., returning Sat, Sep 6, priced at $83 found 4 days ago
Thu, Sep 11 - Sun, Sep 14
BWI
Baltimore Washington Intl. Thurgood Marshall
ORD
O'Hare Intl.
$84 Roundtrip, just found
$84
Roundtrip
just found
Select Spirit Airlines flight, departing Thu, Sep 11 from Baltimore Washington Intl. Thurgood Marshall to O'Hare Intl., returning Sun, Sep 14, priced at $84 just found
Tue, Jul 22 - Tue, Jul 29
MCO
Orlando Intl.
ORD
O'Hare Intl.
$87 Roundtrip, found 15 hours ago
$87
Roundtrip
found 15 hours ago
Select Spirit Airlines flight, departing Tue, Jul 22 from Orlando Intl. to O'Hare Intl., returning Tue, Jul 29, priced at $87 found 15 hours ago
Thu, Sep 4 - Mon, Sep 8
BWI
Baltimore Washington Intl. Thurgood Marshall
MDW
Midway Intl.
$88 Roundtrip, found 4 days ago
$88
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Thu, Sep 4 from Baltimore Washington Intl. Thurgood Marshall to Midway Intl., returning Mon, Sep 8, priced at $88 found 4 days ago
Wed, Oct 8 - Tue, Oct 14
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$88 Roundtrip, found 3 days ago
$88
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Wed, Oct 8 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Tue, Oct 14, priced at $88 found 3 days ago
Sun, Sep 21 - Sun, Sep 21
MCO
Orlando Intl.
MDW
Midway Intl.
$105 Roundtrip, found 4 days ago
$105
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Sun, Sep 21 from Orlando Intl. to Midway Intl., returning Sun, Sep 21, priced at $105 found 4 days ago
Sat, Sep 20 - Sat, Sep 20
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$132 Roundtrip, found 14 hours ago
$132
Roundtrip
found 14 hours ago
Select Delta flight, departing Sat, Sep 20 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sat, Sep 20, priced at $132 found 14 hours ago

Southwest Side ORD Flight Information

Traveling To
Southwest Side
Destination Airport IATA Code
CHI
Number of Airlines Serving
17
Airlines
Spirit Airlines, Southwest Airlines, Frontier Airlines, Delta
Flight Price
$72
Earliest Departing Flight
AA 4487 6:03AM EDT
Latest Departing Flight
AS 6398 Jul 14 8:28PM EDT

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.
Four Points by Sheraton Chicago Schaumburg
3.0-star property

Four Points by Sheraton Chicago Schaumburg

Aug 19 - Aug 24

5 night stay

Los Angeles (LAX) to Chicago (ORD)

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

Arlo Chicago

Aug 15 - Aug 18

3 night stay

Dallas (DAL) to Chicago (ORD)

Southwest Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 18 hours ago
Park Hyatt Chicago
5.0-star property

Park Hyatt Chicago

Aug 29 - Aug 31

2 night stay

Dallas (DFW) 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.
Hotel Felix River North/Magnificent Mile
4.0-star property

Hotel Felix River North/Magnificent Mile

8.2/10 Very Good! (1,785 reviews)

Aug 26 - Aug 31

5 night stay

New York (JFK) to Chicago (ORD)

Delta • Roundtrip • PremiumEconomy
Save 100% on your flight
per person
found 16 hours ago
Great location for doing things downtown. Walkable to every where one wants to go, or a cheap Lyft ride.

Reviewed on May 1, 2025

Hilton Chicago
4.0-star property

Hilton Chicago

8.4/10 Very Good! (1,950 reviews)

Aug 26 - Aug 31

5 night stay

New York (JFK) to Chicago (ORD)

Delta • Roundtrip • PremiumEconomy
Save 100% on your flight
per person
found 16 hours ago
The check in staff went out of their way to accommodate our combining of two separate reservations. The staff responded quickly to all our requests, and staff in general were very friendly. The room was a bit small, but this can be expected in a downtown location.

Reviewed on Jul 7, 2025

The Allegro Royal Sonesta Hotel Chicago Loop
4.0-star property

The Allegro Royal Sonesta Hotel Chicago Loop

8.8/10 Excellent! (1,796 reviews)

Aug 26 - Aug 31

5 night stay

New York (JFK) to Chicago (ORD)

Delta • Roundtrip • PremiumEconomy
Save 100% on your flight
per person
found 16 hours ago
Attitude of the people was outstanding!! Very friendly and helpful.

Reviewed on Jun 13, 2025

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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 18

4 night stay

New York (NYC) to Chicago (ORD)

American Airlines • Non-stop • FirstClass

Chicago (ORD) to New York (NYC)

Delta • Non-stop • FirstClass
per person
found 16 hours ago
Old school, nice and clean

Reviewed on Jun 21, 2025

Swissotel - Chicago
4.5-star property

Swissotel - Chicago

8.8/10 Excellent! (2,274 reviews)

Aug 14 - Aug 18

4 night stay

New York (NYC) to Chicago (ORD)

American Airlines • Non-stop • FirstClass

Chicago (ORD) to New York (NYC)

Delta • Non-stop • FirstClass
per person
found 16 hours ago
Clean and attentive staff

Reviewed on Jun 21, 2025

Arlo Chicago
4.0-star property

Arlo Chicago

9.2/10 Wonderful! (1,769 reviews)

Aug 14 - Aug 18

4 night stay

New York (NYC) to Chicago (ORD)

American Airlines • Non-stop • FirstClass

Chicago (ORD) to New York (NYC)

Delta • Non-stop • FirstClass
per person
found 16 hours ago
Fantastic stay, amazing location.

Reviewed on Jun 25, 2025

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Southwest Side

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First-Timers

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Ports and Play

Be sure to check our cruise page for free shore excursions, onboard spending, balcony upgrades and other perks. Orbitz offers last-minute, luxury, weekend and summer cruises. You can even designate which port you want to sail from and pre-book on-shore activities. Get there on the cheap with discounts on flights to Southwest Side and Southwest Side flights. Get more bang for your travel buck at Orbitz.

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 $72 to $132 this week. Arriving from Atlanta (ATL)? The most affordable one-way fares were $32.
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.