We noticed that you're using an unsupported browser. The Tripadvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Find the best flight to Chicago

ReturnOne-wayMulti-city
Tripadvisor will not show you ads based on your previous online behaviour or personal data. You may see it because the operator shown offers travel-related services that may match your search and has paid our advertising partner, QuoteLab LLC (trading as MediaAlpha) to appear. When you click, we earn commission from MediaAlpha.
To help you compare prices, we may redirect this page to a different travel operator when you click on “Find flights”.

Great deals to Chicago

We’ve searched 100s of deals recently found by travellers.*
Boston, MA (BOS) Chicago, IL (CHI)
€63
Mon, 26/8 - Tue, 27/8
Spirit Airlines - Roundtrip, Economy
New York City, NY (NYC) Chicago, IL (CHI)
€66
Tue, 10/9 - Tue, 10/9
Spirit Airlines - Roundtrip, Economy
Barcelona, ES (BCN) Chicago, IL (CHI)
€317
Tue, 5/11 - Sun, 17/11
TAP Air Portugal - Roundtrip, Economy
Frankfurt, DE (FRA) Chicago, IL (CHI)
€330
Thu, 7/11 - Thu, 21/11
Aer Lingus - Roundtrip, Economy
Dublin, IE (DUB) Chicago, IL (CHI)
€333
Tue, 5/11 - Tue, 12/11
Icelandair - Roundtrip, Economy
Athens, GR (ATH) Chicago, IL (CHI)
€362
Fri, 8/11 - Sun, 10/11
British Airways - Roundtrip, Economy
Bilbao, ES (BIO) Chicago, IL (CHI)
€371
Thu, 19/9 - Mon, 23/9
TAP Air Portugal - Roundtrip, Economy
Madrid, ES (MAD) Chicago, IL (CHI)
€379
Fri, 6/9 - Sun, 15/9
TAP Air Portugal - Roundtrip, Economy
*Prices are based on round trip travel with returns between 1-21 days after departure. These are the best fares found by travellers who searched Tripadvisor and a select group of our fare search partners in the past 72 hours. Ticket prices and seat availability change rapidly and cannot be guaranteed.

Direct flights to Chicago

Sorry, we couldn't find any direct flights that match your search. Try searching for another airport and/or date.

Flight stats for Chicago - did you know?

  • Chicago is 25 km from O'Hare Intl Airport (Chicago, IL).
  • O'Hare Intl Airport (Chicago, IL)
    • Right now, 68 airlines operate out of O'Hare Intl Airport.
    • O'Hare Intl Airport offers nonstop flights to 211 cities.
    • Every week, at least 11,349 domestic flights and 732 international flights depart from O'Hare Intl Airport.
  • Chicago is 14 km from Midway Airport (Chicago, IL).
  • Midway Airport (Chicago, IL)
    • Right now, 8 airlines operate out of Midway Airport.
    • Midway Airport offers nonstop flights to 76 cities.
    • Every week, at least 1,263 domestic flights and 33 international flights depart from Midway Airport.
Show more
Hotels with free wifi in Chicago
The Neighborhood Hotel Little Italy
The Neighborhood Hotel Little Italy
78 Reviews
Chicago, IL
from
Trump International Hotel & Tower Chicago
Trump International Hotel & Tower Chicago
4,832 Reviews
Chicago, IL
from
Ray's Bucktown Bed And Breakfast
Ray's Bucktown Bed And Breakfast
462 Reviews
Chicago, IL
from