Cheap flights To DeKalb (CHI) from $29

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Cheap Flights to DeKalb from $29 One Way, $56 Round Trip

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

Wed, Aug 12 - Wed, Aug 19
FLL
Fort Lauderdale - Hollywood Intl.
ORD
O'Hare Intl.
$56 Roundtrip, found 19 hours ago
$56
Roundtrip
found 19 hours ago
Select Frontier Airlines flight, departing Wed, Aug 12 from Fort Lauderdale - Hollywood Intl. to O'Hare Intl., returning Wed, Aug 19, priced at $56 found 19 hours ago
Wed, May 20 - Thu, May 21
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$72 Roundtrip, found 5 days ago
$72
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Wed, May 20 from George Bush Intercontinental to O'Hare Intl., returning Thu, May 21, priced at $72 found 5 days ago
Tue, May 19 - Wed, May 27
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$108 Roundtrip, found 2 days ago
$108
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Tue, May 19 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Wed, May 27, priced at $108 found 2 days ago
Mon, Jun 1 - Wed, Jun 10
LGA
LaGuardia
ORD
O'Hare Intl.
$111 Roundtrip, found 2 days ago
$111
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Mon, Jun 1 from LaGuardia to O'Hare Intl., returning Wed, Jun 10, priced at $111 found 2 days ago
Thu, May 28 - Wed, Jun 3
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$154 Roundtrip, found 15 hours ago
$154
Roundtrip
found 15 hours ago
Select Frontier Airlines flight, departing Thu, May 28 from Los Angeles Intl. to O'Hare Intl., returning Wed, Jun 3, priced at $154 found 15 hours ago
Thu, May 28 - Fri, May 29
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$168 Roundtrip, found 2 days ago
$168
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Thu, May 28 from Newark Liberty Intl. Airport to O'Hare Intl., returning Fri, May 29, priced at $168 found 2 days ago
Tue, Aug 18 - Tue, Aug 25
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$169 Roundtrip, found 5 days ago
$169
Roundtrip
found 5 days ago
Select United flight, departing Tue, Aug 18 from George Bush Intercontinental to O'Hare Intl., returning Tue, Aug 25, priced at $169 found 5 days ago
Tue, Aug 18 - Tue, Aug 25
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$169 Roundtrip, found 5 days ago
$169
Roundtrip
found 5 days ago
Select American Airlines flight, departing Tue, Aug 18 from George Bush Intercontinental to O'Hare Intl., returning Tue, Aug 25, priced at $169 found 5 days ago
Tue, Jul 7 - Tue, Jul 14
LGA
LaGuardia
RFD
Greater Rockford
$176 Roundtrip, found 4 days ago
$176
Roundtrip
found 4 days ago
Select American Airlines flight, departing Tue, Jul 7 from LaGuardia to Greater Rockford, returning Tue, Jul 14, priced at $176 found 4 days ago
Tue, Jun 23 - Thu, Jul 2
EWR
Newark Liberty Intl. Airport
RFD
Greater Rockford
$176 Roundtrip, found 4 days ago
$176
Roundtrip
found 4 days ago
Select American Airlines flight, departing Tue, Jun 23 from Newark Liberty Intl. Airport to Greater Rockford, returning Thu, Jul 2, priced at $176 found 4 days ago

DeKalb Flight Information

Traveling To
DeKalb
Destination Airport IATA Code
CHI
Number of Airlines Serving
Airlines
Frontier Airlines, Spirit Airlines, American Airlines, United
Flight Price
$56
Earliest Departing Flight
Latest Departing Flight

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DeKalb 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

Jun 27 - Jun 30

3 night stay

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

Spirit Airlines • Coach

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

American Airlines • Coach
Save 100% on your flight
Price was $943, price is now $559 per person
$559
per person
found 1 day ago
Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0-star property

Sable at Navy Pier Chicago, Curio Collection by Hilton

Jun 27 - Jun 30

3 night stay

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

Spirit Airlines • Coach

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

American Airlines • Coach
Save 100% on your flight
Price was $1,232, price is now $811 per person
$811
per person
found 1 day ago
Level Chicago – Old Town
4.0-star property

Level Chicago – Old Town

Jun 18 - Jun 21

3 night stay

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

American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,454, price is now $992 per person
$992
per person
found 1 day ago
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DeKalb premium economy flight packages

Price found within the past 48 hours. Click for updated prices.
LondonHouse Chicago, Curio Collection by Hilton
4.5-star property

LondonHouse Chicago, Curio Collection by Hilton

9.4/10 Exceptional! (3,670 reviews)

Jun 4 - Jun 8

4 night stay

New York (NYC) to Chicago (ORD)

Frontier Airlines • Non-stop • PremiumEconomy

Chicago (ORD) to New York (NYC)

JetBlue Airways • Non-stop • PremiumEconomy
Price was $1,948, price is now $1,419 per person
$1,419
per person
found 10 hours ago
Amazing view!! Great rooftop at night!!! Drinks were excellent Expresso Martini!!

Reviewed on Mar 30, 2026

Swissotel - Chicago
4.5-star property

Swissotel - Chicago

9/10 Wonderful! (3,293 reviews)

Jun 4 - Jun 8

4 night stay

New York (NYC) to Chicago (ORD)

Frontier Airlines • Non-stop • PremiumEconomy

Chicago (ORD) to New York (NYC)

JetBlue Airways • Non-stop • PremiumEconomy
Price was $2,470, price is now $1,633 per person
$1,633
per person
found 10 hours ago
Great stay and we highly recommend. We will be back.

Reviewed on Apr 21, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0-star property

Sable at Navy Pier Chicago, Curio Collection by Hilton

9.4/10 Exceptional! (2,478 reviews)

Jun 4 - Jun 8

4 night stay

New York (NYC) to Chicago (ORD)

Frontier Airlines • Non-stop • PremiumEconomy

Chicago (ORD) to New York (NYC)

JetBlue Airways • Non-stop • PremiumEconomy
Price was $2,087, price is now $1,520 per person
$1,520
per person
found 10 hours ago
Courteous staff, clean room, conveniently located right on the pier.

Reviewed on Nov 3, 2025

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DeKalb first class flight packages

Price found within the past 48 hours. Click for updated prices.
Wind Creek Southland Casino and Hotel
4.0-star property

Wind Creek Southland Casino and Hotel

9.4/10 Exceptional! (336 reviews)

Jun 26 - Jun 28

2 night stay

New York (NYC) to Chicago (ORD)

Delta • Non-stop roundtrip • FirstClass
Price was $1,076, price is now $877 per person
$877
per person
found 12 hours ago
Love the Cleanliness, and no smoking rooms. The staff was excellent! We will attend again

Reviewed on Nov 17, 2025

voco Chicago Downtown - Riverwalk by IHG
3.5-star property

voco Chicago Downtown - Riverwalk by IHG

8.8/10 Excellent! (3,760 reviews)

Jun 26 - Jun 28

2 night stay

New York (NYC) to Chicago (ORD)

Delta • Non-stop roundtrip • FirstClass
Price was $1,127, price is now $1,038 per person
$1,038
per person
found 12 hours ago
I loved the pool and the restaurant within the hotel. Great customer service. I had a great view. The room was a tad bit smaller than I expected for the price but it was a nice hotel.

Reviewed on Feb 9, 2026

Canopy by Hilton Chicago Central Loop
4.0-star property

Canopy by Hilton Chicago Central Loop

9.4/10 Exceptional! (1,481 reviews)

Jun 26 - Jun 28

2 night stay

New York (NYC) to Chicago (ORD)

Delta • Non-stop roundtrip • FirstClass
Price was $1,165, price is now $1,088 per person
$1,088
per person
found 12 hours ago
the best Hilton so far.

Reviewed on Feb 26, 2026

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DeKalb

When you plan to buy tickets for flights to DeKalb, you don’t have to look any further than Orbitz! We offer bargain rates and low fares on thousands of flights.

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Along with our low prices, Orbitz is well known for exceptional customer care. We make it simple to find the best DeKalb flights for you. If you need to cancel your booking or change your flight plans, simply contact our Customer Service department to make any adjustments.

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If you like the ease of making your travel plans on the move, you’ll love the free Orbitz apps for iPhones, iPads, and Android devices. You can use these apps to review your travel reservations or make a change to your itinerary. Orbitz also offers additional travel assistance such as free mobile alerts that keep you up-to-date about sudden changes to your upcoming flights. You can also browse Orbitz easily on your smartphone by using the mobile version of the website to find budget DeKalb flights.

Frequently asked questions

Which airlines fly to DeKalb?
You can select from 20 airlines that operate services to O'Hare Intl. Airport (ORD), the primary airport in the city. With a good range of options, you're certain to pick up a terrific deal. Here are some of the international airlines that'll get you to DeKalb — and then discovering every corner of this city:

  • United Airlines - 612 flights to DeKalb per month
  • American Airlines - 339 flights to DeKalb per month
  • Air Canada - 190 flights to DeKalb per month

How much is a flight to DeKalb?
Prices for round-trip flights to DeKalb this week ranged between $56 and $176. If you were flying one-way from Fort Lauderdale (FLL), you could have bagged prices from just $29.
How to book the cheapest flight to DeKalb?
With some of the biggest and best flight deals around, you can jet for less with Orbitz. The following handy hints will help you snap up cheap flights to DeKalb — and leave you with more money to play with:

  • Depending on your departure city, select the 'Nearby airports' function (located under the departure and arrival options). In some cases, other departure points offer cheaper airfares.
  • Also, click on the 'Show flexible dates' link to compare the prices on days either side of your selected departure. You may be able to score cheaper flight deals if you're flexible with your dates.
  • You can also use the 'Show options' link to filter results for your preferred carrier, seating class, nonstop flights and refundable flights. Under 'Sort & Filter' to the left, you can even choose the time of day you want to fly.
  • Book your airfare as soon as you've decided on your travel dates. While it does happen now and then, airfares rarely drop in price as your departure date approaches.
  • Make even more savings on your adventure by combining your hotel, flights and car rentals into an Orbitz package deal. Your credit card will thank you.
  • Whenever possible, don't fly in peak seasons. Airfares often hit their highest during school breaks, summer and other vacation periods like Easter and Christmas.

What is the best time to book a flight to DeKalb?
Generally speaking, the cheapest time to book a seat is in January. This is closely followed by February and August. When looking for a cheap flight to DeKalb, make sure you're ready to book. Cheap deals pop up quickly and don't hang around!
What day of the week is the cheapest to book a flight to DeKalb?
To score a great flight deal, book on a Tuesday, Wednesday or Saturday. These are generally the cheapest days to purchase tickets to DeKalb.
What is the cheapest day of the week to fly to DeKalb?
According to Orbitz data from 2020, you ought to kick off your trip on a Monday to nab cheap flights to DeKalb. Next cheapest day? Tuesday. Saturday costs the most. So, think about departing early in the week if you'd like to score a low-priced fare and stretch your travel budget.
What is the cheapest month to fly to DeKalb?
Get set to jet for less in August. This is generally the best month to get on a plane if you're looking for cheap flights to DeKalb, based on Orbitz data. The costliest time to fly is June, so avoid this month if you can.
Which airlines allow free cancellation?
We understand that plans change and flexibility is important. That's why you can 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 lollipop left in the sun!
What do I need for the flight to DeKalb?
The key to a comfortable flight is preparation. Here are some handy tips to help you get ready for take off:

  • Whether you print it out at home or use an electronic one, you'll need your boarding pass to step foot on the plane. You'll also need some form of government-issued photo ID. If you're traveling internationally, make sure your passport is valid and you've looked into visa requirements.
  • Make time fly by even quicker on your short flight by packing the right stuff. Think snacks, a water bottle and entertainment. If you'd like your journey to DeKalb to go quietly, squeeze some headphones in your carry-on bag too.
  • Even if you're flying when it's 100 degrees outside, bring a sweater or cardigan on board with you. Airplane cabins can get downright chilly.

How do I get cheap first-class/business deals to DeKalb?
There are ways of booking first or business-class fares to DeKalb that won't burn a hole through your budget. Bag a seat at the front of the plane for less with these helpful tips:

  • Flexibility is key. By being open to a variety of travel dates, you'll have more chances of picking up a great deal on business or first-class airfares.
  • Search for a budget airline that has seats in business class. They usually come with extra legroom and a glass of Champagne — and a more appealing price.
  • Take advantage of your airline's loyalty program and upgrade your seat. Alternatively, you can try bidding for an upgrade in an online auction if available.

What is the best time to go to DeKalb?
DeKalb is busy in June, July and August. If you're arranging a visit during these months, it would be wise to book well in advance to ensure you snap up the greatest deals. Curious to know what summer's like in DeKalb? Average daily temperatures usually fluctuate between 65 ºF and 80 ºF. Like most destinations in the Northern Hemisphere, the summer season begins June 20 here.
Travel tips for DeKalb

  • Downtown DeKalb is brimming with terrific attractions. Tourist spots like Northern Illinois University and Star Worlds Arcade will keep your feet on the move and your adventurous spirit full.
  • You'll also want to see the sights within an easy drive of DeKalb's center. Set out for Chicago Premium Outlets and Aurora University and see a different side of this sought-after destination.
  • When you want to explore more of Illinois, book a car rental and cruise to Chicago. Peoria is another popular city with a wealth of things to see and do.

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.