Cheap flights from Chicago from $38
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago departing on 8/25. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
Find, compare and book domestic and international flights departing from Chicago
Discover deals from 900+ travel sites with momondo.
Save money when you book flights with momondo
Big names and deals
Big names and deals
Search 100s of travel sites to compare prices.Filter for what you want
Filter for what you want
Free Wi-Fi? Stopover? Instantly customize your results.Trusted and free
Trusted and free
We’re completely free to use - no hidden charges or fees.Price Alerts
Price Alerts
Not ready to book? to track prices.Where can I directly fly to from Chicago?
Currently, 100 destinations can be reached directly via flights from Chicago.
Find the cheapest flights from Chicago
Cheap one-way flights from Chicago
Last-minute flight deals from Chicago
Cheapest international flights from Chicago
Cheapest domestic flights from Chicago
Flights from Chicago - Travel Insights & Trends
Get data-powered insights and trends into flights from Chicago to help you craft the best travel plan.
What are the most popular domestic flights out of Chicago?
According to searches, the most popular destinations for domestic flights from Chicago among momondo users are Los Angeles, Charlotte, Rapid City, Jacksonville and Traverse City.
Which international cities can I fly to direct from Chicago?
momondo search trends show that the most popular international cities to visit when flying direct from Chicago include Guadalajara, Morelia, Guatemala City, Puerto Vallarta, and Brussels.
What are the most popular places to fly to from Chicago?
Based on momondo flight searches, the most popular place to fly from Chicago is Seattle (21% of total searches). The next most popular destinations are New York (7%) and Los Angeles (6%). Searches for flights from Chicago to Las Vegas (5%), to Denver (4%) and to Dallas (4%) are also popular.
What are the most popular international flights out of Chicago?
There are many places you can fly to from Chicago. The most popular international destinations according to searches among momondo users are flights to Tokyo, flights to San Juan and flights to Paris.
What is the shortest direct flight from Chicago?
From Chicago, the shortest direct flight is to Milwaukee, with a flight time of 48m. The next fastest flight is to Muskegon, which takes 50m, followed by Grand Rapids at 50m.
What is the longest direct flight from Chicago?
The longest direct flight you can take from Chicago is to New Delhi, with a duration of 16h 35m. The next longest is Hong Kong at 15h 50m, followed by a flight to Taipei City at 15h 05m.
Frequently asked questions regarding flights from Chicago
Which airlines are currently offering the cheapest flights from Chicago?
Our data suggests that currently, the cheapest flights from Chicago are being offered by American Airlines, Delta, and Frontier. For example, American Airlines flights from Chicago to Amman, start at $13, Delta flights from Chicago to Fort Lauderdale cost around $39, and Frontier flights from Chicago to Raleigh are around $45.
What is the cheapest flight available from Chicago?
Currently, the cheapest flight from Chicago found by our users is for $38 to Louisville. Prices will vary according to several factors such as the departure date and time, but on average you can expect to pay around $233 to travel from Chicago to Louisville.
Which destinations have the most frequent flights from Chicago?
New York, Los Angeles and Atlanta are currently the destinations served most frequently from Chicago, with 124, 82 and 77 flights per day on average, respectively.
Which airlines can you fly with from Chicago?
Airlines including American Airlines, Delta and Southwest frequently fly from Chicago. You can view other airlines by performing a quick search in the form above.
What is the cheapest first class flight from Chicago?
If you are looking for a cheap first class flight, consider flights to Nashville, for which the starting price of a first class seat can be as low as $279.
When did momondo last update prices for flights from Chicago?
Prices for flights from Chicago are updated daily.
How many operators does momondo search for flights from Chicago?
There are 79 operators available for flights from Chicago as of July 2025.
How old do you have to be to fly from Chicago?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago.
What documentation or ID do you need to fly to Chicago?
The travel and health documents you'll need for your trip to Chicago may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.