Cheap flights To Deerfield (CHI) from $29

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

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

Sun, Jan 25 - Sun, Feb 1
JFK
John F. Kennedy Intl.
ORD
O'Hare Intl.
$58 Roundtrip, found 2 hours ago
$58
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Sun, Jan 25 from John F. Kennedy Intl. to O'Hare Intl., returning Sun, Feb 1, priced at $58 found 2 hours ago
Sat, Mar 21 - Wed, Mar 25
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$58 Roundtrip, found 17 hours ago
$58
Roundtrip
found 17 hours ago
Select Frontier Airlines flight, departing Sat, Mar 21 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Wed, Mar 25, priced at $58 found 17 hours ago
Tue, Jan 13 - Sun, Jan 18
EWR
Newark Liberty Intl. Airport
MDW
Midway Intl.
$59 Roundtrip, found 16 hours ago
$59
Roundtrip
found 16 hours ago
Select Frontier Airlines flight, departing Tue, Jan 13 from Newark Liberty Intl. Airport to Midway Intl., returning Sun, Jan 18, priced at $59 found 16 hours ago
Sat, Feb 14 - Sat, Feb 21
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$59 Roundtrip, found 17 hours ago
$59
Roundtrip
found 17 hours ago
Select Frontier Airlines flight, departing Sat, Feb 14 from Dallas-Fort Worth Intl. to Midway Intl., returning Sat, Feb 21, priced at $59 found 17 hours ago
Tue, Jan 20 - Tue, Jan 20
LGA
LaGuardia
ORD
O'Hare Intl.
$63 Roundtrip, found 20 hours ago
$63
Roundtrip
found 20 hours ago
Select Spirit Airlines flight, departing Tue, Jan 20 from LaGuardia to O'Hare Intl., returning Tue, Jan 20, priced at $63 found 20 hours ago
Sat, Jan 24 - Mon, Jan 26
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$72 Roundtrip, found 1 hour ago
$72
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Sat, Jan 24 from Newark Liberty Intl. Airport to O'Hare Intl., returning Mon, Jan 26, priced at $72 found 1 hour ago
Thu, Jan 15 - Sun, Jan 18
JFK
John F. Kennedy Intl.
ORD
O'Hare Intl.
$97 Roundtrip, just found
$97
Roundtrip
just found
Select American Airlines flight, departing Thu, Jan 15 from John F. Kennedy Intl. to O'Hare Intl., returning Sun, Jan 18, priced at $97 just found
Thu, Jan 15 - Sun, Jan 18
LGA
LaGuardia
ORD
O'Hare Intl.
$97 Roundtrip, just found
$97
Roundtrip
just found
Select United flight, departing Thu, Jan 15 from LaGuardia to O'Hare Intl., returning Sun, Jan 18, priced at $97 just found
Sat, Jan 17 - Mon, Jan 26
JFK
John F. Kennedy Intl.
ORD
O'Hare Intl.
$97 Roundtrip, found 3 hours ago
$97
Roundtrip
found 3 hours ago
Select JetBlue Airways flight, departing Sat, Jan 17 from John F. Kennedy Intl. to O'Hare Intl., returning Mon, Jan 26, priced at $97 found 3 hours ago
Thu, Jan 22 - Sat, Jan 24
LGA
LaGuardia
MDW
Midway Intl.
$99 Roundtrip, found 1 day ago
$99
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Thu, Jan 22 from LaGuardia to Midway Intl., returning Sat, Jan 24, priced at $99 found 1 day ago

Deerfield Flight Information

Traveling To
Deerfield
Destination Airport IATA Code
CHI
Number of Airlines Serving
Airlines
Frontier Airlines, Spirit Airlines, Southwest Airlines, JetBlue Airways, United, American Airlines
Flight Price
$58
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

Deerfield economy flight packages

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

Swissotel - Chicago

Feb 6 - Feb 8

2 night stay

Houston (IAH) to Chicago (ORD)

Spirit Airlines • Roundtrip • Coach
Price was $232, price is now $167 per person
$167
per person
found 1 day ago
Trump International Hotel & Tower Chicago
5.0-star property

Trump International Hotel & Tower Chicago

Jan 28 - Jan 31

3 night stay

Washington (DCA) to Chicago (ORD)

American Airlines • Coach

Chicago (ORD) to Washington (DCA)

JetBlue Airways • Coach
Save 100% on your flight
Price was $1,059, price is now $748 per person
$748
per person
found 1 hour ago
Level Chicago – Old Town
4.0-star property

Level Chicago – Old Town

Feb 19 - Feb 22

3 night stay

Houston (IAH) to Chicago (ORD)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $555, price is now $395 per person
$395
per person
found 3 hours ago
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Deerfield premium economy flight packages

Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town
4.0-star property

Level Chicago – Old Town

9/10 Wonderful! (380 reviews)

Feb 16 - Feb 22

6 night stay

Las Vegas (LAS) to Chicago (ORD)

Delta • Non-stop roundtrip • PremiumEconomy
Price was $1,443, price is now $1,018 per person
$1,018
per person
found 1 day ago
We always love staying here. Such great service and nice accommodations.

Reviewed on Nov 20, 2025

The Emily Hotel
4.0-star property

The Emily Hotel

9.2/10 Wonderful! (1,264 reviews)

Feb 16 - Feb 22

6 night stay

Las Vegas (LAS) to Chicago (ORD)

Delta • Non-stop roundtrip • PremiumEconomy
Price was $1,595, price is now $1,088 per person
$1,088
per person
found 1 day ago
Cute and trendy hotwl but there was a loud party on-site which ruined experience. It felt clean but our mini fridge had takeout left from former guest, so maid service obviously missed that.

Reviewed on Jul 26, 2025

Trump International Hotel & Tower Chicago
5.0-star property

Trump International Hotel & Tower Chicago

9.4/10 Exceptional! (1,773 reviews)

Feb 16 - Feb 22

6 night stay

Las Vegas (LAS) to Chicago (ORD)

Delta • Non-stop roundtrip • PremiumEconomy
Save 100% on your flight
Price was $2,199, price is now $1,600 per person
$1,600
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

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Deerfield 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 13 - Feb 15

2 night stay

Miami (MIA) to Chicago (ORD)

United • Roundtrip • FirstClass
Price was $951, price is now $825 per person
$825
per person
found 1 day ago
Staff is TOP NOTCH! I am in a wheelchair right now, recovering from a knee surgery, and staff could not have been more solicitous and helpful. Also, when we checked in, upon learning of my daughter‘s birthday on Christmas, the front desk representative gave us a complementary room upgrade and sent up chocolates! The room was very clean and the shower was fantastic. Not enough good words about the buffet, as long as you’re clear that it is a “breakfast“ buffet and not a “brunch“ buffet :-). I think I was expecting a sliced roast beef and an omelette bar, but it is in fact a very extensive selection of breakfast foods. The restaurant recommendation was spot on. We had a delicious dinner of fine Mediterranean/Sardinian foodat Nora’s next door and enjoyed it immensely. I have now joined the capital RIU club and plan on spending much more time at their other properties, particularly in Costa Rica, where I am moving next month. Kudos to all, and thank you for our wonderful stay!

Reviewed on Dec 28, 2025

The Peninsula Chicago
5.0-star property

The Peninsula Chicago

9.8/10 Exceptional! (1,003 reviews)

Feb 13 - Feb 15

2 night stay

Miami (MIA) to Chicago (ORD)

United • Roundtrip • FirstClass
Price was $1,348, price is now $1,143 per person
$1,143
per person
found 1 day ago
Everything was superb. The only “complaint “ I have, is that I paid for a city view room, but actually looked at the side of one building. Other than that, we lived the stay.

Reviewed on Oct 24, 2025

Trump International Hotel & Tower Chicago
5.0-star property

Trump International Hotel & Tower Chicago

9.4/10 Exceptional! (1,773 reviews)

Feb 13 - Feb 15

2 night stay

Miami (MIA) to Chicago (ORD)

United • Roundtrip • FirstClass
Price was $1,241, price is now $1,063 per person
$1,063
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

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Deerfield

Orbitz is your one stop for guaranteed low prices on Deerfield flights, as well as budget deals on hotels and rental cars. Use our state of the art mobile tools to get great deals and constant updates on the status of your trip.

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Our state of the art mobile apps will allow you to book cheap flights to Deerfield from your smartphone too. Discount airfare is not all; you can also find mobile-only hotel deals or check the status of your flight using this free app. So, when you’re on the go, why not take Orbitz with you?

Frequently asked questions

Which airlines fly to Deerfield?
With 20 airlines providing services to O'Hare Intl. Airport (ORD), a major entry point to Deerfield, the choice is yours. Find an unbeatable deal among these leading international carriers waiting to whisk you away to this city:

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

What is the best airport to fly to in Deerfield?
Hop on a flight to O'Hare Intl. Airport (ORD) and get ready to explore the sights and sounds of this city. The airport is around 14 miles south of the center of town. Also compare fares to Midway Intl. Airport (MDW), which is another entrance point to Deerfield.
How much is a flight to Deerfield?
If you're looking for round-trip flights, fares ranged between $58 and $99 this week. The most affordable one-way ticket prices were $29, originating in New York (JFK).
How to book the cheapest flight to Deerfield?
With some of the most amazing flight deals around, bagging a bargain is easy with Orbitz. The following hints and tips will help you land cheap flights to Deerfield — and leave you with more cash to splash:

  • Departing from or landing at other airports can sometimes help you save on airfares. Enter your preferred departure and arrival points. Next, click on the 'Nearby airports' function below to see what your options are.
  • If you're flexible with your plans, click on the 'Show flexible dates' link. It'll show the flight deals for the days either side of your chosen departure. Ticket prices often vary depending on what day of the week it is.
  • You can also use the 'Show options' function 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'd prefer to fly.
  • Once you've worked out your travel dates, get booking. Prices normally get dearer as the departure date nears.
  • Make greater savings on your trip by combining your hotel, flights and car rental into a package with Orbitz. Your credit card will thank you for it.
  • Don't travel during the busy season if possible. By steering clear of school vacations and summer, you can save loads on your airfares.

How long is a flight to Deerfield?
Flight times vary based on where you're jetting in from. But to give you a good idea of the average duration, have a peek at these well-known routes to Deerfield:

  • 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 Deerfield?
Generally speaking, January is the ideal time to book your airfare. This is closely followed by February and August. Bear this in mind while you search for a cheap flight to Deerfield.
What day of the week is the cheapest to book a flight to Deerfield?
To land a rewarding flight deal, book on a Tuesday, Wednesday or Saturday. These are typically the cheapest days of the week to purchase flights to Deerfield.
What is the cheapest day of the week to fly to Deerfield?
Based on Orbitz data from 2020, Monday is generally the best day to get cheap flights to Deerfield. Tuesday also has budget-friendly airfares, whereas Saturday has the highest ticket prices. Even though flying out at the weekend can be more suitable, you'll have more money in your pocket to play with if you set off earlier in the week.
What is the cheapest month to fly to Deerfield?
To score cheap flights to Deerfield, you should pack your suitcase and fly out in August. Orbitz data has found that generally, this is the best month to save a bundle on your fare. If you're considering flying to Deerfield in June, bear in mind that this is the most expensive time to take a trip.
Which airlines allow free cancellation?
Flexible travel is more important than ever, that's why Orbitz lets you search for carriers that won't hit you with a fee for making amendments. Add your departure and arrival destinations, then choose "Filter by flexible change policies." We'll show you options that include free cancellation and no change fees.
What do I need for the flight to Deerfield?
There's nothing like flying off to a cool new destination, but it's good to be prepared. This list of useful tips will help get your trip off to a great start:

  • Whether you print it out beforehand or use an electronic one, you'll need your boarding pass to get on to the plane. You'll also need some kind of government-issued identification. If you're flying internationally, make sure your passport is valid and you've looked into visa requirements.
  • To keep you busy on the short trip to Deerfield, download some new tunes or restock the audiobook library on your tablet. Food can also be a welcome distraction while in the air, so maybe even bring some snacks.
  • Whatever the weather's doing outside, plane cabins can get a bit chilly. Bring a sweater on board to keep yourself comfortable.

How many direct flights are there to Deerfield?
With approximately 2,332 direct flights every month, you'll be heading straight into Deerfield and embarking on your next exciting adventure in no time. Some of the carriers that travel nonstop to Deerfield include United Airlines, American Airlines and Delta Air Lines. Southwest Airlines, Spirit Airlines and Air Canada are some other frequently booked options.
How do I get cheap first-class/business deals to Deerfield?
If you think a business or first-class airfare is beyond your reach, you may want to think again. Here are a few practical tips to help you pick up a premium flight to Deerfield for a whole lot less:

  • Flexibility isn't confined to yoga. Have some room to move around your travel dates so you can snap up more affordable airfares when they pop up.
  • Search for a budget carrier that offers seats in business class. They usually come with extra space and a glass of Champagne — and a more affordable price.
  • Bid for an upgrade. Some airlines hold online auctions that let you put down a price for a seat at the front of the plane. You may also be able to upgrade with points earned through a flight loyalty scheme.

How to get into Deerfield from the airport?
Cruise into central Deerfield with an O'Hare Intl. Airport (ORD) car rental. Thrifty Car Rental and Dollar are two well-known suppliers at O'Hare Intl. Airport (ORD). Toss your baggage in the trunk, drive 14 miles to the north and you'll be in the heart of the city in no time at all. Many travelers also use public transportation or taxis to head into town from the airport. From there, you can still rent a ride to see the region's other great attractions with one of our Deerfield car rentals.
What is the best time to go to Deerfield?
Deerfield is a popular place in May, June and July. If you're contemplating visiting during these months, it would be a good idea to book ahead of time to ensure you get the most rewarding deals. Curious to know what summer's like in Deerfield? Average daily temperatures usually fluctuate between 65 ºF and 80 ºF. Like most places in the Northern Hemisphere, summer begins June 20 here.
Travel tips for Deerfield

  • Downtown Deerfield has plenty of renowned attractions. Drawcards like Marriott Theatre and Sportsman's Country Club will keep your feet on the move and your adventurous spirit happy.
  • If you're in search of a day trip, there are more sights to see a short drive out of town. Discover why Wrigley Field and McCormick Place are on the must-do lists of many Deerfield travelers.
  • When you want to get out and experience more of Chicago, book a car rental and set your GPS for Calumet City. Naperville is another worthwhile city with no shortage of things to do and see.

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.