Cheap flights To Northern Illinois (CHI) from $111

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Cheap Flights to Northern Illinois from $111 One Way, $181 Round Trip

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

Tue, Apr 28 - Wed, May 13
PWM
Portland Intl. Jetport
ORD
O'Hare Intl.
$181 Roundtrip, found 6 days ago
$181
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Tue, Apr 28 from Portland Intl. Jetport to O'Hare Intl., returning Wed, May 13, priced at $181 found 6 days ago
Tue, Apr 28 - Tue, May 12
PWM
Portland Intl. Jetport
ORD
O'Hare Intl.
$201 Roundtrip, found 6 days ago
$201
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Tue, Apr 28 from Portland Intl. Jetport to O'Hare Intl., returning Tue, May 12, priced at $201 found 6 days ago
Thu, Mar 12 - Mon, Mar 16
PWM
Portland Intl. Jetport
ORD
O'Hare Intl.
$209 Roundtrip, found 11 hours ago
$209
Roundtrip
found 11 hours ago
Select American Airlines flight, departing Thu, Mar 12 from Portland Intl. Jetport to O'Hare Intl., returning Mon, Mar 16, priced at $209 found 11 hours ago
Tue, Apr 28 - Mon, May 11
PWM
Portland Intl. Jetport
ORD
O'Hare Intl.
$226 Roundtrip, found 6 days ago
$226
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Tue, Apr 28 from Portland Intl. Jetport to O'Hare Intl., returning Mon, May 11, priced at $226 found 6 days ago
Thu, Mar 12 - Mon, Mar 16
PWM
Portland Intl. Jetport
ORD
O'Hare Intl.
$229 Roundtrip, found 11 hours ago
$229
Roundtrip
found 11 hours ago
Select Delta flight, departing Thu, Mar 12 from Portland Intl. Jetport to O'Hare Intl., returning Mon, Mar 16, priced at $229 found 11 hours ago
Fri, Jan 16 - Mon, Jan 19
BZN
Bozeman Yellowstone Intl.
ORD
O'Hare Intl.
$229 Roundtrip, found 4 days ago
$229
Roundtrip
found 4 days ago
Select American Airlines flight, departing Fri, Jan 16 from Bozeman Yellowstone Intl. to O'Hare Intl., returning Mon, Jan 19, priced at $229 found 4 days ago
Fri, Jan 16 - Mon, Jan 19
BZN
Bozeman Yellowstone Intl.
ORD
O'Hare Intl.
$229 Roundtrip, found 4 days ago
$229
Roundtrip
found 4 days ago
Select United flight, departing Fri, Jan 16 from Bozeman Yellowstone Intl. to O'Hare Intl., returning Mon, Jan 19, priced at $229 found 4 days ago
Sun, Jan 18 - Fri, Jan 23
BZN
Bozeman Yellowstone Intl.
ORD
O'Hare Intl.
$234 Roundtrip, found 5 hours ago
$234
Roundtrip
found 5 hours ago
Select Alaska Airlines flight, departing Sun, Jan 18 from Bozeman Yellowstone Intl. to O'Hare Intl., returning Fri, Jan 23, priced at $234 found 5 hours ago
Mon, Apr 27 - Tue, May 12
PWM
Portland Intl. Jetport
ORD
O'Hare Intl.
$234 Roundtrip, found 6 days ago
$234
Roundtrip
found 6 days ago
Select Delta flight, departing Mon, Apr 27 from Portland Intl. Jetport to O'Hare Intl., returning Tue, May 12, priced at $234 found 6 days ago
Fri, Feb 6 - Tue, Feb 10
BZN
Bozeman Yellowstone Intl.
ORD
O'Hare Intl.
$238 Roundtrip, found 3 days ago
$238
Roundtrip
found 3 days ago
Select Alaska Airlines flight, departing Fri, Feb 6 from Bozeman Yellowstone Intl. to O'Hare Intl., returning Tue, Feb 10, priced at $238 found 3 days ago

Northern Illinois Flight Information

Traveling To
Northern Illinois
Destination Airport IATA Code
CHI
Number of Airlines Serving
Airlines
Delta, American Airlines, Alaska Airlines, JetBlue Airways, United
Flight Price
$181
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

Book Your Flight & Hotel Together & Save

Northern Illinois 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

Feb 4 - Feb 8

4 night stay

Atlanta (ATL) to Chicago (ORD)

Spirit Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $343, price is now $239 per person
$239
per person
found 1 day ago
DoubleTree by Hilton Lisle Naperville
4.0-star property

DoubleTree by Hilton Lisle Naperville

Feb 14 - Feb 22

8 night stay

Atlanta (ATL) to Chicago (ORD)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $585, price is now $377 per person
$377
per person
found 3 hours ago
Motel Edgebrook Chicago North Shore by OYO
2.0-star property

Motel Edgebrook Chicago North Shore by OYO

Feb 14 - Feb 22

8 night stay

Atlanta (ATL) to Chicago (ORD)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $520, price is now $349 per person
$349
per person
found 3 hours ago
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See all available trips from Atlanta to Northern Illinois
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Northern Illinois first class flight packages

Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Chicago Schaumburg
4.0-star property

DoubleTree by Hilton Chicago Schaumburg

7.2/10 Good! (1,003 reviews)

Feb 18 - Feb 22

4 night stay

Boston (BOS) to Chicago (ORD)

American Airlines • Roundtrip • FirstClass
Price was $739, price is now $676 per person
$676
per person
found 4 hours ago
Great property, phenomenal experience

Reviewed on Oct 6, 2025

Hilton Chicago O'Hare Airport
4.0-star property

Hilton Chicago O'Hare Airport

8.2/10 Very Good! (2,158 reviews)

Feb 18 - Feb 22

4 night stay

Boston (BOS) to Chicago (ORD)

American Airlines • Roundtrip • FirstClass
Price was $1,141, price is now $959 per person
$959
per person
found 4 hours ago
Awesome hotel, an island of peace and calm and first class treatment in a sea of chaos at O'Hare airport. Staff, restaurant, services--worth every penny. Early departure? Stay here the night before. We did. Calmly woke up and walked to the terminal thru the underground walkways. Truly pleasant and memorable stay.

Reviewed on Nov 11, 2025

Hilton Rosemont Chicago O'Hare
3.5-star property

Hilton Rosemont Chicago O'Hare

8.4/10 Very Good! (1,000 reviews)

Feb 18 - Feb 22

4 night stay

Boston (BOS) to Chicago (ORD)

American Airlines • Roundtrip • FirstClass
Price was $915, price is now $834 per person
$834
per person
found 4 hours ago
Good hotel close to airport, with free airport shuttle, 7-10 min away. Quite convenient

Reviewed on Nov 4, 2025

Don't see what you're looking for?
See all available trips from Boston to Northern Illinois
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Northern Illinois

Reach your destination without breaking your budget by booking your flights to Northern Illinois using Orbitz. We offer access to all of the best discounts on airfare, travel accommodations and even car rentals. Planning your trip and saving money are easier with Orbitz.

Get Discount Rates On Your Northern Illinois Flight

Whether planning ahead or deciding to book your trip at the last minute, Orbitz will provide the lowest rates on Northern Illinois flights. Using our free mobile phone apps will make you privy to a number of discounts that are unique to mobile phone users. These are perfect for harried travelers who want to find deals that they can qualify for on the same day.

Make Orbitz Your Official Travel Planner

Orbitz can be used for much more than comparing and booking a discount flight to Northern Illinois. We also offer a variety of resources for securing the ideal travel accommodations while staying on budget. Travel tips, hotel reviews, customized suggestions and even detailed images can all be accessed through your mobile phone.

Build A Comprehensive Travel Itinerary

In addition to booking a low cost flight to Northern Illinois, you can learn about the best places to visit, the best hotels to stay in and the preferred times for traveling. When you use Orbitz mobile phone apps you can also share your travel itineraries with friends and family members, all with just a few quick taps.

Using Orbitz to secure your Northern Illinois flights can save you money and time. Perfect for both the early travel planner and the last minute journey: Orbitz offers phenomenal customer service and unbeatable convenience.

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Frequently asked questions

What is the best airport to fly to in Northern Illinois?
Williamson County Regional Airport (MWA) is the major gateway for this terrific destination. Once you've stepped out of the terminal, the possibilities are endless when it comes to adventuring around Northern Illinois.
How much is a flight to Northern Illinois?
Travelers from far and wide bagged round-trip bargains ranging from $181 to $238 this week. Kicking off your journey from Bozeman (BZN)? The cheapest one-way prices were just $111.
How to book the cheapest flight to Northern Illinois?
Scoring cheap flights to Northern Illinois is as easy as booking with Orbitz. But if you'd like to make sure you're walking away with the best flight deals around, here are some tips to keep in mind:

  • Departing from or landing at nearby airports can often be more affordable. Enter your preferred departure and arrival points. Next, select the 'Nearby airports' function below to explore your options.
  • Similarly, click on the 'Show flexible dates' link to compare the prices on days either side of your chosen departure. It's possible to find cheaper flight deals if your travel dates are flexible.
  • Select 'Show options' to narrow down your search results. You can pick your preferred seating class and airline here. Under 'Sort & Filter' to the left, you can even specify whether you'd like to fly in the morning, afternoon or evening.
  • The early bird gets the best savings, so purchase your seats once you've settled on your travel dates. The most affordable fares get snapped up first and prices normally increase as the departure date nears.
  • Consider bundling your hotels, flights and car rentals into an Orbitz package to make your dollar go further.
  • Don't fly during the busy season if you can. By avoiding summer, school vacations and other popular dates, you can save big on your airfares.

What is the best time to book a flight to Northern Illinois?
Book in January, February or August for unbeatable fares to Northern Illinois. Once you've found a bargain, lock it in — cheap flights are known to appear and then vanish in the click of a button.
What day of the week is the cheapest to book a flight to Northern Illinois?
In general, Tuesdays, Wednesdays and Saturdays are the cheapest days of the week to book a flight to Northern Illinois. If you want the best airfares, search across those days and you're likely to catch an excellent flight deal.
What is the cheapest day of the week to fly to Northern Illinois?
You can land cheap flights to Northern Illinois by flying out on a Monday, according to Orbitz data from 2020. Tuesday is also more affordable, while Saturday has the most costly ticket prices. Whether you prefer to save a bundle or fly out on whichever day is convenient, you'll always get a terrific deal with Orbitz.
What is the cheapest month to fly to Northern Illinois?
Consider traveling in August if you don't want to put a dent in your budget. Orbitz data has found that it's generally the best month for cheap flights to Northern Illinois. June is when fares really go up.
Which airlines allow free cancellation?
When you search for flights on Orbitz, select "Filter by flexible change policies." This filter will quickly find all the airlines offering free cancellation within 24 hours of booking and no change fees. That means you can relax knowing that if your travel dates change, your flight can too.
What do I need for the flight to Northern Illinois?
Flying can be fun with a little pre-planning! Make your flight a relaxing one with these helpful tips:

  • Whether you print it out or use an electronic one, you'll need your boarding pass to step foot on the plane. You'll also need some kind of government-issued photo identification. If you're flying internationally, make sure your passport is valid and you've looked into visa requirements.
  • Take some activities to keep you amused on your journey to Northern Illinois. Books, magazines and electronic gadgets like laptops and tablets are good ideas. Be sure to take a refillable water bottle with you too. Even on a short flight, it's important to keep well-hydrated.
  • It can get very cool on the plane. If you'd prefer not to shiver your way through the flight, layer up.

How many direct flights are there to Northern Illinois?
With 13 direct flights each month, getting to Northern Illinois doesn't have to be long and stressful. Cape Air offers nonstop services to this bustling destination.
How do I get cheap first-class/business deals to Northern Illinois?
If you think a business or first-class airfare is beyond your grasp, think again. Here are some terrific tips to help you book a premium flight to Northern Illinois for less:

  • Flexibility is everything. By being open to different travel dates, you'll have more chances of spotting a sale on first or business-class airfares.
  • Find a budget airline that has business-class seats. They usually come with more space and a glass of bubbly — and a more appealing price.
  • Bid for an upgrade in online auctions (if available) or upgrade your seat through your frequent flyer program.

What is the best time to go to Northern Illinois?
Northern Illinois is a wonderful getaway destination year-round, but the most popular months are June, July and August. If you're into warm weather, make your way there during the summer months. Like most places in the Northern Hemisphere, the summer season commences June 20. At this time, temperatures usually float between 65 ºF and 80 ºF during the daytime.

More to Explore

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.