$25 Cheap flights to Chicago
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight to Chicago departing on 5/28. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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What is the cheapest month to fly to Chicago?
The month of September is, on average, the cheapest month to fly to Chicago from United States, with most prices found around $176. If you’re not able to fly to Chicago in September, then January is your next best option. Flight prices from United States to Chicago during January average around $179.
What is the absolute cheapest flight to Chicago?
In the past two weeks, users have booked deals to Chicago for $73/person, which is 68% cheaper than the average flight to Chicago. To find the cheapest price to Chicago from your area, use momondo’s Airport-to-Airport Pricing Tool.
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What is the cheapest day to depart on your flight to Chicago?
The cheapest day to depart on your flight to Chicago is on a Wednesday when prices can be found for as low as $291. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from United States to Chicago for around $376.
What is the cheapest time of day to depart on your flight to Chicago?
Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from United States to Chicago during this time can be as low as $236. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $341.
Cheapest flights to Chicago
Find the cheapest flights to Chicago from your nearest city or airport
| CHEAPEST MONTH TO FLY TO CHICAGO FROM LOS ANGELES | February | 18% cheaper | Flying from Los Angeles to Chicago costs on average just $246 in February |
| MOST EXPENSIVE MONTH TO FLY TO CHICAGO FROM LOS ANGELES | December | 11% more expensive | It costs about $335 for flights to Chicago from Los Angeles in December |
| MOST POPULAR MONTH TO FLY TO CHICAGO FROM LOS ANGELES | July | 275% more users visited | More momondo users searched in flights to Chicago from Los Angeles in July than any other month |
Cheap Chicago flight deals and tips
Summary info about Chicago flight prices, duration and airlines
Best One-Way Price | $25 |
|---|---|
Best Round-Trip Price | $75 |
Fastest flight time | 2h 32m |
Popular in | December |
Frequently asked questions about flying to Chicago
When is it best to fly to Chicago to go sightseeing?
The best time to plan to fly to Chicago to go sightseeing would be when the temperature is not unbearable and the chance of rain is only moderate. Considering those guidelines, May or June seems like the best time of year to plan your visit.
How far in advance should I book a flight to Chicago?
The best time to book a flight to Chicago from United States is 35 days out, which is when prices tend to be around $226. Don’t hesitate to check prices now though because momondo users recently found tickets for as low as $166.
Is there an alternative airport near Chicago?
Finding an alternative and possibly cheaper destination airport near Chicago is possible. If you are planning a flight to Chicago, consider booking flights to Chicago Midway Airport (9 mi from Chicago city center) or Chicago Greater Rockford Airport (79 mi from Chicago city center).
Is there a cheaper alternative to flying into Chicago?
The cheapest airport near Chicago is typically Chicago Greater Rockford Airport with an average price of $168/person. These prices vary based on where travelers are coming from. It is suggested that travelers looking to save money try momondo’s Airport-to-Airport Pricing Tool.
Are there flights to Downtown?
Yes. To go to Downtown, book a flight to Chicago O'Hare Intl which is in Chicago and is about 15.7 mi away from Downtown.
What’s the closest airport to Magnificent Mile?
Chicago O'Hare Intl in Chicago is the closest airport to Magnificent Mile (distance: 15.5 mi).
When did momondo last update prices for flights to Chicago?
Prices for flights to Chicago are updated daily.
How many operators does momondo search for flights to Chicago?
As of April 2025, there are 64 operators available to choose from for flights to Chicago.
How old do you have to be to fly to Chicago?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel to 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.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsWhy use momondo?
Why should I use momondo to find a flight deal to Chicago?
We help find the flight that best suits your needs; momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight for you.
Can I find flights to Chicago with flexible booking policies on momondo?
Yes. momondo allows you to filter the results for flights to Chicago to just show those with flexible booking policies.
How can momondo help me find flights to Chicago?
Once you have performed a search for flights to Chicago, momondo helps you find the right flight by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.
I’m not ready to book a flight to Chicago right now. Can momondo alert me if prices change?
If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago and alert you when they change.
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Popular flights to Chicago
Popular routes according to searches in the past day on momondo
Cheapest flight routes to Chicago
These routes have the cheapest flights to Chicago found by momondo users in United States
| Departing | Destination | Best Time | Best Price |
|---|---|---|---|
| Tampa | Chicago | 2h 38m | $60 |
| Asheville | Chicago | 1h 39m | $65 |
| Knoxville | Chicago | 1h 33m | $68 |
| Nashville | Chicago | 1h 31m | $69 |
| Miami | Chicago | 3h 21m | $71 |
| Fort Lauderdale | Chicago | 3h 13m | $75 |
| Newark | Chicago | 2h 32m | $75 |
| Burlington | Chicago | 1h 40m | $79 |
| Orlando | Chicago | 3h 03m | $80 |
| Las Vegas | Chicago | 3h 35m | $82 |
| Atlanta | Chicago | 2h 07m | $83 |
| Valparaiso | Chicago | 2h 22m | $87 |
| Savannah | Chicago | 2h 05m | $87 |
| Baltimore | Chicago | 2h 00m | $95 |
| Phoenix | Chicago | 3h 05m | $95 |
| Dallas | Chicago | 2h 10m | $95 |