Flying to Chicago
Start with the shape of the trip
Chicago is a major hub for both business and leisure—museums, deep-dish pizza, and lakefront views. Two airports serve the city: O'Hare and Midway. Checking both can save you money.
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Flights to Chicago
Find cheap flights to Chicago. Compare O'Hare and Midway and book on our partner site.
Main airport
ORD - Chicago
Best for
Short city breaks
Travel style
city
Airports
Flight and airport guide
O'Hare (ORD) is one of the busiest airports in the world, with flights to and from almost everywhere. Midway (MDW) is smaller and south of the loop; several budget carriers fly there, so fares are often lower. Train and bus links connect both to downtown. Use the search form above to compare ORD and MDW for your dates.
Timing
Best time to visit Chicago
Demand (and prices) peak in summer and around Thanksgiving and Christmas. For better deals, aim for January–March or September–October. Midweek travel usually costs less than weekends.
If you're flexible on which airport you use, always run a search that includes both. The difference can be fifty dollars or more each way.
Highlights
Why visit Chicago
Short city breaks
Keep this in mind when you compare airport options, dates, and total trip cost.
Culture-first trips
Keep this in mind when you compare airport options, dates, and total trip cost.
Shoulder-season value
Keep this in mind when you compare airport options, dates, and total trip cost.
Better-value fares
How to find cheap flights to Chicago
Use the search form above to compare fares to Chicago. Enter your departure city and dates, then sort by price or stops. When you see a fare you like, click through to book on our partner site; we don't charge booking fees.
Search nearby airports
A nearby airport can be cheaper than the obvious one, especially when a city is served by multiple airports or regional alternatives.
Avoid peak travel days
Friday departures and Sunday returns often cost more. Midweek combinations are usually a better place to start.
Look outside the busiest season
Shoulder-season trips can deliver better fares, shorter lines, and more flexible flight options.
Review the full trip cost
The cheapest headline fare is not always the best value after carry-on fees, seat selection, and airport transfer costs.
F.A.Q
Chicago O'Hare (ORD) is the main hub with most domestic and international flights. Midway (MDW) is smaller and often has lower fares on budget carriers.
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