$29 Cheap Flights to North Side, IL

View $29 flight on Sat, May 2, 2026Opens in a new window

Popular airlines

  • Delta

  • Frontier Airlines

  • American Airlines

  • United

  • Spirit Airlines

  • Southwest Airlines

  • Alaska Airlines

How much is the cheapest flight to North Side?

Prices were available within the past 7 days and start at $29 for one-way flights and $56 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Thu, Apr 30 - Sun, May 3
EWR
New York
MDW
Chicago
$56 Roundtrip, just found
$56
Roundtrip
just found
Select Frontier Airlines flight, departing Thu, Apr 30 from New York to Chicago, returning Sun, May 3, priced at $56 just found
Spirit Airlines
Tue, Apr 21 - Wed, Apr 29
DFW
Dallas
ORD
Chicago
$87 Roundtrip, found 2 hours ago
$87
Roundtrip
found 2 hours ago
Select Spirit Airlines flight, departing Tue, Apr 21 from Dallas to Chicago, returning Wed, Apr 29, priced at $87 found 2 hours ago
American Airlines
Tue, Jun 23 - Sat, Jun 27
EWR
New York
RFD
Rockford
$176 Roundtrip, found 3 hours ago
$176
Roundtrip
found 3 hours ago
Select American Airlines flight, departing Tue, Jun 23 from New York to Rockford, returning Sat, Jun 27, priced at $176 found 3 hours ago
Delta
Wed, Aug 5 - Wed, Aug 12
LGA
New York
ORD
Chicago
$177 Roundtrip, just found
$177
Roundtrip
just found
Select Delta flight, departing Wed, Aug 5 from New York to Chicago, returning Wed, Aug 12, priced at $177 just found
United
Wed, Aug 5 - Wed, Aug 12
EWR
New York
ORD
Chicago
$177 Roundtrip, just found
$177
Roundtrip
just found
Select United flight, departing Wed, Aug 5 from New York to Chicago, returning Wed, Aug 12, priced at $177 just found

Alternative airports

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Flights from $315
ORD
O'Hare Intl.
Flights from $315
Select flight to Midway Intl. MDW. Cheapest option available. Flights from $201
MDW
Midway Intl.
Cheapest
Flights from $201

Frequently asked questions

What month is the cheapest to fly to North Side?
The cheapest month to fly to North Side is April when demand is low. Off-peak months are usually when you'll find cheap fares. To save money, avoid flying during major holidays and school breaks.
Which US cities have the cheapest flights to North Side?
Typically, New York, Washington and Dallas offer cheap flights to North Side. However, flexibility is key to getting the best deals. Plan your escape during the off-peak season or midweek to keep costs down.
Which US cities fly direct to North Side?
Pick from 150 US cities offering direct flights to North Side. When you book on Expedia, click on the "Direct flights only" box to find nonstop options. Fly to North Side from any of these cities:

  • New York
  • Washington
  • Dallas
  • Boston
  • Phoenix

How to find a cheap flight to North Side?
To secure cheap flights to North Side, book in advance or travel during the off-season months of December and January. Want a handy tip? Jet off on a Thursday and save around 16% on average compared to traveling on a Sunday.* Opt to receive price alerts on the Expedia app and we'll let you know as soon as your fares go down.*Best day of the week to book, depart and ideal booking window recommendations based on average round-trip ticket prices for January through August 2023, sourced from Airline Reporting Corporation's (ARC) global airline sales database. Percentages noted are averages.
How to get a cheap last-minute flight to North Side?
Being flexible about your travel plans might help you to find last-minute offers on cheap flights to North Side. To see all the available options, consider exploring different ticket types, changing your North Side trip dates, flying out of an alternative airport or going with another carrier.
How far in advance should I book a flight to North Side?
Lock in your flight to North Side two to four months ahead if you're flying in from an international destination. For domestic travel, the timeframe is around 28 days in advance. Better deals and a greater choice of departure dates, times and seating options are some of the great reasons to book early.**Best day of the week to book, depart and ideal booking window recommendations based on average round-trip ticket prices for January through August 2023, sourced from Airline Reporting Corporation's (ARC) global airline sales database. Percentages noted are averages.
Which day of the week is the cheapest day to buy a plane ticket to North Side?
You can generally get cheap flights to North Side on a Sunday. Travelers can save around 8% on average compared to booking on a Friday, which is often the most expensive day for tickets.**Best day of the week to book, depart and ideal booking window recommendations based on average round-trip ticket prices for January through August 2023, sourced from Airline Reporting Corporation's (ARC) global airline sales database. Percentages noted are averages.
Which airlines fly to North Side?
You can choose from a variety of airlines that fly to North Side. A few of your top options are:

  • United Airlines - 13,391 flights to North Side each month, including 13,391 flights to O'Hare Intl. Airport (ORD) per month.
  • American Airlines - 10,417 flights to North Side each month, including 10,417 flights to O'Hare Intl. Airport (ORD) per month.
  • Delta Air Lines - 1,213 flights to North Side each month, including 1,213 flights to O'Hare Intl. Airport (ORD) per month.

Where do you fly into North Side?
The main hub when you fly to North Side is Midway Intl. Airport (MDW), but there are other nearby options like O'Hare Intl. Airport (ORD) and Lewis University Airport (LOT). You can also land at Chicago Executive Airport (PWK) and Gary, IN (GYY-Gary - Chicago Intl.) when flying to North Side.
Can I save money by booking a North Side trip package?
You could potentially save hundreds of dollars if you choose a North Side flight and hotel package deal on Expedia. And you'll save time and hassle by having all your travel arrangements in one place. Try bundling flights and hotels with extras such as car rentals and tours for your own personalized North Side getaway.
Can I change or cancel my flight to North Side?
If you bought your flight to North Side within the last 24 hours, you can often cancel or change it for free. After that, additional costs may apply depending on the airline's rules and restrictions. For more information, head to our Customer Service Portal. Bear in mind that some flights are non-refundable, so you may be offered a credit for future flights in place of a direct refund. When searching on Expedia, select the "Changes included" or "No cancel fee" filters to compare fares with flexible change policies.

*Flight schedules are subject to change.

*Available to One Key members.

 

Travel information

Destination airport
Midway Intl.
Destination airport IATA code
MDW
Destination city name
Chicago
Roundtrip price
$56

Trending flights to North Side

Prices were available within the past 7 days and start at $29 for one-way flights and $56 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Thu, Apr 30 - Sun, May 3
EWR
New York
MDW
Chicago
$56 Roundtrip, just found
$56
Roundtrip
just found
Select Frontier Airlines flight, departing Thu, Apr 30 from New York to Chicago, returning Sun, May 3, priced at $56 just found

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