$42 Cheap Flights from Chicago
One-way
Departing from
Chicago
Going to
anywhere
Knoxville (TYS)
United States • May, 2026
94% AI deal score
$483 $42
Punta Gorda (PGD)
United States • May, 2026
92% AI deal score
$423 $52
Asheville (AVL)
United States • May, 2026
89% AI deal score
$250 $46
Destin (VPS)
United States • May, 2026
89% AI deal score
$380 $61
Austin (AUS)
United States • May, 2026
84% AI deal score
$270 $49
This is the lowest one-way flight price found by RatePunk users in the last 24 hours for a flight going to anywhere. Fares are subject to change and may not be available for all dates. (Data last updated 5/26/2026).
385,365 searches in the past 7 days on RatePunk
Flight deals up to 90% off
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AI deal score and AI insights
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Top Destinations Where Can You Fly from Chicago
Cheap flights from Chicago
Knoxville, United States
TOP
May • Direct
$483
$42
-$441
91%
Asheville, United States
TOP
May • Direct
$250
$46
-$204
82%
Austin, United States
TOP
May • Direct
$270
$49
-$221
82%
Philadelphia, United States
TOP
May • Direct
$258
$40
-$218
84%
San Juan, United States
TOP
May • Direct
$270
$44
-$226
84%
Destin, United States
TOP
Jun • Direct
$353
$41
-$312
88%
Find flights from Chicago to anywhere
Looking for inspiration on destinations? Here are some popular flight deals from Chicago one-way fares:
See more destinations you can fly to from Chicago – anywhere in the world at the best prices.
See More DestinationsFacts About Flights from Chicago
Nearby airport(s)
Insights for flights from Chicago
Most popular airlines from Chicago
American Airlines
Alaska Airlines, Inc.
JetBlue Airways
Delta Air Lines
Frontier Airlines
Spirit Airlines
United Airlines
Virgin America
Most popular destinations from Chicago
ORD Airport Deal Stats
Current most discounted routes
Avg. most discounted routes (last 3 months)
ORD airport insights
Best days to catch a deal
Wednesday, Sunday
Based on the data, you're most likely to find the cheapest flight deals originating from O'Hare International Airport on Wednesdays and Sundays. However, it is important to remember that deals are dependent on many factors, so you should check frequently for the best prices.
Avg. deal survival time
10.1 hours
Deals that originate from O'Hare International Airport last an average of 10.1 hours. This means you need to act fast to secure these flight deals!
Rare deal frequency
12 deals
We found 12 rare deals originating from O Hare International airport in the past month. These rare deals, which typically include mistake fares, special promotions, or ultra-discounts, achieved an AI Deal Score of 90+.
Average price drop
-69%
Deals that originate from O Hare International Airport see an average price drop of 69.4%. This means that travelers can save a significant amount on flights by taking advantage of deals from O Hare International Airport.
Next 4 weeks: deal forecast
O'Hare International Flight Forecast - Next Month
Based on current trends, flight deals from O'Hare International are expected to remain relatively stable next month. There may be slight price increases due to the approaching summer travel season.
Top 5 biggest price drops (last 3 months)
Found on April 30
ORD - Abbotsford
$693 → $86
88%
Found on April 26
ORD - Salta
$1,675 → $416
75%
Found on April 26
ORD - Sekondi-Takoradi
$4,100 → $1,066
74%
Found on April 27
ORD - Rio de Janeiro
$1,165 → $300
74%
Found on April 26
ORD - Bariloche
$1,600 → $415
74%
Check these nearby airports too
Looking for more options? These airports near ORD sometimes drop rare deals too:
Gerald R. Ford International (GRR)
~5 rare deals/month
General Mitchell International (MKE)
~12 rare deals/month
Chicago Rockford International (RFD)
~6 rare deals/month
If you’re flexible with departure cities, it’s worth keeping an eye on nearby airports — especially GRR and MKE for long-haul deal surprises.
Travel Trends: Popular Destinations from Chicago
Every month, we analyze search and booking data to see where travelers from Chicago are heading. Here are the current hot destinations from Chicago:
Top domestic destinations
These cities are seeing the most searches and bookings from Chicago this month.
Top international destinations
Travelers from Chicago are flocking here, possibly due to seasonal events or great deals.
Travel trend insight
Travelers from Chicago are increasingly drawn to destinations with rich history and cultural experiences. London and Rome remain popular due to their iconic landmarks, historical significance, and vibrant cultural scenes, offering diverse attractions for a wide range of travelers.
Booking Flights from Chicago: Frequently Asked Questions
Pro Tips for Finding Cheap Flights from Chicago
Finding the cheapest airfare from Chicago is easier if you use a few smart strategies. Here are our top tips to help you score a great deal:
Be Flexible with Dates: Wiggle room with your travel dates can lead to sweet savings. Mid-week flights or traveling during the shoulder season (spring/fall) often means lower prices, leaving you with extra cash for deep-dish pizza in Chicago!
Set Destination to 'Anywhere': Feeling adventurous? Set your destination to 'Anywhere' on flight search engines. You might stumble upon an unbelievably cheap flight to a destination you've never considered, opening up a world of new experiences.
Embrace the Off-Peak: Avoid the herds and save some serious dough by traveling during off-peak times. Think post-summer, pre-holiday season. You'll enjoy fewer crowds and more money in your pocket for exploring Chicago's awesome neighborhoods.
Explore Nearby Airports: Chicago has multiple airports, and sometimes flying in or out of a smaller, less popular one can save you a bundle. Don't be afraid to check out all your options – a little extra travel time might be worth the savings!
Mix and Match Flights: Sometimes, booking two one-way tickets with different airlines beats the price of a round-trip. It requires a bit more searching, but the potential savings can be substantial, leaving you more to spend on Chicago-style hot dogs.
Loyalty Pays Off: Got points or miles? Now's the time to use them! Redeeming your rewards can significantly cut down the cost of your flight, turning those hard-earned points into a delicious deep-dish pizza (or two) in Chicago.
Early Bird Gets the Worm: While last-minute deals exist, booking in advance often secures the best prices. Start your search a few months ahead of your trip to snag those early-bird discounts and avoid any stressful price hikes.
Sign Up for Fare Alerts on RatePunk: Let RatePunk do the work for you! Set up price alerts for your desired Chicago flights and get notified when prices drop. This way, you'll never miss out on a great deal, ensuring you get the best possible price.
Consider Connecting Flights: Non-stop flights are convenient, but connecting flights can be much cheaper. If you're not in a rush, embrace the layover! It could save you enough money to splurge on a fancy Chicago steak dinner.
Clear Your Browser Cookies: Flight prices can sometimes increase after repeated searches due to cookies tracking your interest. Clear your browser cookies or use incognito mode to see if you can find lower fares on your Chicago-bound flight.
By using these tips and the tools on our site, you’ll increase your chances of finding a fantastic flight deal from Chicago. Happy travels!
Explore More Destinations from Chicago
Looking for more options? Here are some popular routes and related travel deals: