Cheap flights To North Side (CHI) from $29

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Cheap Flights to North Side from $29 One Way, $58 Round Trip

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

Thu, Feb 19 - Fri, Feb 27
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$58 Roundtrip, found 1 day ago
$58
Roundtrip
found 1 day 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 1 day ago
Fri, Feb 27 - Sat, Feb 28
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$58 Roundtrip, just found
$58
Roundtrip
just found
Select Frontier Airlines flight, departing Fri, Feb 27 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sat, Feb 28, priced at $58 just found
Sat, Feb 28 - Mon, Mar 2
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$59 Roundtrip, just found
$59
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, Feb 28 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Mon, Mar 2, priced at $59 just found
Thu, Feb 12 - Tue, Feb 24
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$63 Roundtrip, found 4 days ago
$63
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Thu, Feb 12 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Tue, Feb 24, priced at $63 found 4 days ago
Tue, Feb 17 - Wed, Feb 18
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$64 Roundtrip, found 20 hours ago
$64
Roundtrip
found 20 hours ago
Select Frontier Airlines flight, departing Tue, Feb 17 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Wed, Feb 18, priced at $64 found 20 hours ago
Thu, Jan 29 - Mon, Feb 2
JFK
John F. Kennedy Intl.
ORD
O'Hare Intl.
$67 Roundtrip, just found
$67
Roundtrip
just found
Select Frontier Airlines flight, departing Thu, Jan 29 from John F. Kennedy Intl. to O'Hare Intl., returning Mon, Feb 2, priced at $67 just found
Wed, Feb 11 - Wed, Feb 18
LGA
LaGuardia
ORD
O'Hare Intl.
$71 Roundtrip, just found
$71
Roundtrip
just found
Select Spirit Airlines flight, departing Wed, Feb 11 from LaGuardia to O'Hare Intl., returning Wed, Feb 18, priced at $71 just found
Sat, Feb 14 - Mon, Feb 16
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$75 Roundtrip, just found
$75
Roundtrip
just found
Select Spirit Airlines flight, departing Sat, Feb 14 from Newark Liberty Intl. Airport to O'Hare Intl., returning Mon, Feb 16, priced at $75 just found
Sun, Mar 8 - Tue, Mar 10
EWR
Newark Liberty Intl. Airport
MDW
Midway Intl.
$100 Roundtrip, found 9 hours ago
$100
Roundtrip
found 9 hours ago
Select Frontier Airlines flight, departing Sun, Mar 8 from Newark Liberty Intl. Airport to Midway Intl., returning Tue, Mar 10, priced at $100 found 9 hours ago
Tue, Feb 17 - Wed, Feb 25
LGA
LaGuardia
MDW
Midway Intl.
$117 Roundtrip, found 9 hours ago
$117
Roundtrip
found 9 hours ago
Select Southwest Airlines flight, departing Tue, Feb 17 from LaGuardia to Midway Intl., returning Wed, Feb 25, priced at $117 found 9 hours ago

North Side Flight Information

Traveling To
North Side
Destination Airport IATA Code
CHI
Number of Airlines Serving
Airlines
Frontier Airlines, Spirit Airlines, JetBlue Airways, Southwest Airlines, American Airlines
Flight Price
$58
Earliest Departing Flight
Latest Departing Flight

Book Your Flight & Hotel Together & Save

North Side economy flight packages

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

Arlo Chicago

Mar 8 - Mar 13

5 night stay

Dallas (DAL) to Chicago (ORD)

Southwest Airlines • Coach

Chicago (ORD) to Dallas (DAL)

Delta • Coach
Save 100% on your flight
Price was $859, price is now $573 per person
$573
per person
found 3 hours ago
Level Chicago – Old Town
4.0-star property

Level Chicago – Old Town

Mar 8 - Mar 13

5 night stay

Dallas (DAL) to Chicago (ORD)

Southwest Airlines • Coach

Chicago (ORD) to Dallas (DAL)

Delta • Coach
Save 100% on your flight
Price was $943, price is now $596 per person
$596
per person
found 3 hours ago
The Langham, Chicago
5.0-star property

The Langham, Chicago

Mar 8 - Mar 13

5 night stay

Dallas (DAL) to Chicago (ORD)

Southwest Airlines • Coach

Chicago (ORD) to Dallas (DAL)

Delta • Coach
Save 100% on your flight
Price was $1,403, price is now $939 per person
$939
per person
found 3 hours ago
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North Side premium 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

9.4/10 Exceptional! (2,790 reviews)

Mar 20 - Mar 22

2 night stay

Dallas (DFW) to Chicago (ORD)

Delta • Non-stop roundtrip • PremiumEconomy
Price was $1,030, price is now $872 per person
$872
per person
found 1 day ago
I recommend 100% Everything was good, the staff, room and the food. Also, it is located in a good area.

Reviewed on Jan 14, 2026

Trump International Hotel & Tower Chicago
5.0-star property

Trump International Hotel & Tower Chicago

9.4/10 Exceptional! (1,773 reviews)

Mar 20 - Mar 22

2 night stay

Dallas (DFW) to Chicago (ORD)

Delta • Non-stop roundtrip • PremiumEconomy
Price was $1,273, price is now $1,078 per person
$1,078
per person
found 1 day ago
Food was amazing and the staff was amazing. Room was incredible! Felt like we were royalty on our visit!

Reviewed on Oct 13, 2025

Pendry Chicago
4.5-star property

Pendry Chicago

9.4/10 Exceptional! (1,130 reviews)

Mar 20 - Mar 22

2 night stay

Dallas (DFW) to Chicago (ORD)

Delta • Non-stop roundtrip • PremiumEconomy
Price was $1,121, price is now $989 per person
$989
per person
found 1 day ago
Pendry was historic and great

Reviewed on Jul 5, 2024

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North Side first class 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

9.4/10 Exceptional! (2,790 reviews)

Feb 27 - Mar 4

5 night stay

Dallas (DFW) to Chicago (ORD)

American Airlines • Roundtrip • FirstClass
Price was $1,085, price is now $740 per person
$740
per person
found 1 day ago
I recommend 100% Everything was good, the staff, room and the food. Also, it is located in a good area.

Reviewed on Jan 14, 2026

Trump International Hotel & Tower Chicago
5.0-star property

Trump International Hotel & Tower Chicago

9.4/10 Exceptional! (1,773 reviews)

Feb 27 - Mar 4

5 night stay

Dallas (DFW) to Chicago (ORD)

American Airlines • Roundtrip • FirstClass
Save 100% on your flight
Price was $1,888, price is now $1,205 per person
$1,205
per person
found 1 day ago
Food was amazing and the staff was amazing. Room was incredible! Felt like we were royalty on our visit!

Reviewed on Oct 13, 2025

Waldorf Astoria Chicago
5.0-star property

Waldorf Astoria Chicago

9.4/10 Exceptional! (1,000 reviews)

Feb 27 - Mar 4

5 night stay

Dallas (DFW) to Chicago (ORD)

American Airlines • Roundtrip • FirstClass
Save 100% on your flight
Price was $1,881, price is now $1,325 per person
$1,325
per person
found 1 day ago
Lovely room and spacious bathroom plus all of the high end touches (robes, slippers to soft mats and towels and great bath products and loved the nespresso maker!) View was not great but gym and lobby made up for it; bar was too crowded and we couldn’t get a late checkout but at least it was noon and they held our bags for a few hours!

Reviewed on Dec 31, 2025

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North Side

End your search for discount fares on flights to North Side. Orbitz has all the best prices on North Side flights. With Orbitz, you can expect:

Cheap Deals on Flights to North Side

We offer big discounts and last-minute savings on North Side flights. We make it easy for you to research, plan, and book your flight to North Side — all while offering great low fares. With guaranteed low prices and cutting-edge mobile tools, the perfect trip begins on Orbitz.

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Get alerts, updates, or book your North Side flight or other flights wherever you are. Download our free apps for iPhone, Android, and iPad or visit our mobile site at m.orbitz.com to conveniently review or change your air travel plans. We can also send free alerts about your North Side flight to your email or mobile phone, so you get advance warning about potential disruptions and flight delays. Need to book a hotel with your North Side flight? Access exclusive, mobile-only deals via our mobile site and free apps – even on the same day.

Great Customer Care

We want to make your travel booking experience smooth and easy, from planning and researching North Side flights to the actual booking. If you want to cancel your flight to North Side, many tickets can be conveniently cancelled online. Contact our Customer Service to make changes to your air ticket.

Miles or Points Toward Frequent Flyer Programs

Much like booking with an airline directly, you can earn frequent flyer miles or points on qualified flights to North Side with Orbitz. When completing your booking, just fill in your frequent flyer number for the airline you are flying with or for one of its available partner airlines.

Frequently asked questions

How much is a flight to North Side?
Round-trip prices fell as low as $58 this week to North Side, and reached a high of $117. Passengers departing New York (JFK) managed to pick up one-way flights starting at just $29.
How to book the cheapest flight to North Side?
With some of the biggest and best flight deals around, you can jet for less with Orbitz. The following suggestions will help you land cheap flights to North Side — and leave you with extra cash in your wallet:

  • Consider other airports to save money. Enter your preferred departure and arrival airports in the form fields, then select the 'Nearby airports' function below. It will list the available options.
  • Similarly, click on the 'Show flexible dates' link and you'll see the prices on days either side of your chosen departure. You may be able to score cheaper flight deals if your dates are flexible.
  • Select 'Show options' to narrow down your search results. You can pick your preferred airline and seating class here. Under 'Sort & Filter' to the left, you can even select whether you want to fly in the morning, afternoon or evening.
  • Book as soon as you've figured out your travel dates. While you can get lucky once in a while, airline tickets rarely get more affordable as your departure date nears.
  • Think about combining your flights, hotels and car rental into a package deal to make your dollar go further.
  • Don't travel during peak seasons if you can. By avoiding school vacations and summer, you can save plenty on your airfare.

How long is a flight to North Side?
You might have time to read a few chapters of your book, or you might make it though the whole thing! The length of a flight depends on where you're traveling from, but these top routes to North Side will offer some insight:

  • 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 North Side?
Generally speaking, the cheapest time to purchase your airfare is January. This is followed by February then August. When seeking a cheap flight to North Side, it's always good to be ready to book. Cheap deals appear suddenly and don't hang around!
What day of the week is the cheapest to book a flight to North Side?
To find an incredible flight deal, book on a Tuesday, Wednesday or Saturday. Typically, these are the cheapest days of the week to purchase tickets to North Side.
What is the cheapest day of the week to fly to North Side?
Look into departing early in the week for cheap flights to North Side. Orbitz data from 2020 suggests Monday is typically the most inexpensive day to head off, followed by Tuesday. Saturdays were shown to have the most expensive ticket prices. This is probably because many passengers choose to start their break after a long working week.
What is the cheapest month to fly to North Side?
If you have some wiggle room with your travel dates, consider departing in August. Orbitz data shows that this is generally the best month to travel if you're looking for cheap flights to North Side. As you would expect, fares climb in June and flights sell out fast.
Which airlines allow free cancellation?
We understand that plans change and flexibility is more important than ever. That's why you can easily search for flights that have free cancellation and no change fees on Orbitz. Simply click on "Filter by flexible change policies" and we'll show you fares more flexible than a crayon left in the sun!
What do I need for the flight to North Side?
Flying doesn't have to be a drag. In fact it can be a joy with a bit of pre-planning! Make your journey a hassle-free one with these useful tips:

  • Whether you print it out beforehand or use an electronic one, you'll need your boarding pass to step foot on the plane. You'll also need some sort of government-issued ID. If you're flying internationally, make sure your passport is valid.
  • To keep you entertained on the short trip to North Side, download some new tracks or stock up the podcast library on your phone. Food can also be a good distraction while in the air, so take a snack.
  • Even if you're flying in the height of summer, carry a sweater on board with you. Cabins can get quite chilly!

How many direct flights are there to North Side?
Every month, there are 2,332 direct flights into North Side. Choose from an excellent range of airline companies, including United Airlines, American Airlines and Delta Air Lines. Other popular airlines that fly nonstop are Southwest Airlines, Spirit Airlines and Air Canada.
How do I get cheap first-class/business deals to North Side?
Experienced travelers have honed the art of finding business or first-class flights to North Side without the sky-high price tag. Take their lead with these handy tips:

  • Being flexible isn't confined to yoga. Avoid locking in your travel dates so you can pick up more affordable airfares when a big sale comes along.
  • Budget airlines offer first or business-class seats at a fraction of the usual cost. Give the full-service carriers a miss and go with one of these cheaper options.
  • Make a bid for an upgrade. Some airlines hold online auctions that let you offer a price for a seat up the front. You can also try upgrading with points earned through a loyalty program.

What is the best time to go to North Side?
North Side is a popular place in March, May and June. If you're planning to visit during these months, it would be a good idea to book well in advance to ensure you pick up the best deals. Curious to know what summertime's like in North Side? Average daily temperatures usually float between 65 ºF and 75 ºF. Like many destinations in the Northern Hemisphere, summer starts June 20 here.

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.