Chicago Flight Tickets

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Chicago flight deals

* Fares on this page are updated as of Feb 28, 2024 at 9:26 AM EST. They are for One Way or Round Trips as mentioned alongside. These include all taxes and fees and our service fees. Fares based on historical data, may change without prior notice, and can’t be guaranteed until booking confirmation. Please read our terms & conditions carefully.

  • DEN

    Denver

    Apr 24, 2024
  • CHI

    Chicago

    May 01, 2024

$72.94*

Per person inc. Fee

Book Now
  • DFW

    Dallas

    May 14, 2024
  • CHI

    Chicago

    May 18, 2024

$90.94*

Per person inc. Fee

Book Now
  • MCO

    Orlando

    Mar 22, 2024
  • CHI

    Chicago

    Apr 13, 2024

$99.96*

Per person inc. Fee

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  • RSW

    Fort Myers

    Mar 21, 2024
  • ORD

    Chicago

    Apr 03, 2024

$109.18*

Per person inc. Fee

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  • PHL

    Philadelphia

    Jun 01, 2024
  • ORD

    Chicago

    Jun 04, 2024

$112.97*

Per person inc. Fee

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  • PHX

    Phoenix

    Mar 20, 2024
  • CHI

    Chicago

    Mar 26, 2024

$121.67*

Per person inc. Fee

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  • MSP

    Minneapolis St Paul

    Mar 23, 2024
  • CHI

    Chicago

    Apr 20, 2024

$125.20*

Per person inc. Fee

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  • BWI

    Washington

    Mar 25, 2024
  • CHI

    Chicago

    Apr 16, 2024

$140.95*

Per person inc. Fee

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  • LAS

    Las Vegas

    Mar 26, 2024
  • CHI

    Chicago

    Apr 13, 2024

$142.96*

Per person inc. Fee

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  • LGA

    New York

    Apr 04, 2024
  • CHI

    Chicago

    Apr 21, 2024

$145.67*

Per person inc. Fee

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Book Your Chicago Flight Tickets on Red Umbrella Holidays

Do you have Chicago as the next destination you plan to travel to? If the answer is yes, then book your flights to Chicago with Red Umbrella Holidays at an affordable airfare. You can score great deals on your flights and plan a pocket-friendly trip with us.

About flights to Chicago

Q. What is the perfect time to visit Chicago?

Red Umbrella Holidays recommends the ideal time to visit Chicago is from April till June. The Bean City, during these months, experiences the most desirable climate for sightseeing attractions and exploring the city. The months from September to November are ideal for visiting if you wish to avoid large crowds while immersing in various events and festivals throughout the city. This capital city of Illinois is well-known for its cultural landmarks, museums, science centers, and much more.

Q. How far in advance should I book my tickets to fly to Chicago?

Red Umbrella Holidays suggests you should ideally book your flight tickets to Chicago at least three to four weeks in advance before your scheduled departure for great deals.

Q. Which airlines offer the cheapest airfares to Chicago?

Frontier Airlines offers the cheapest airfares to Chicago.

Q. What are the best attractions that I should visit in Chicago?

  • The Art Institute of Chicago
  • Field Museum
  • Navy Pier
  • Millennium Park
  • Shedd Aquarium
  • Cloud Gate
  • Museum of Science and Industry, Chicago

Q. What are the main airport and nearby airports of Chicago?

The main airport of Chicago is Chicago O'Hare International Airport, and its nearby airport option is Chicago Midway International Airport.

Q. Which major airlines are available on Red Umbrella Holidays to fly to Chicago?

Why Book Flights to Chicago with Red Umbrella Holidays?

  • Our vision is to ensure that you have a fun time in Chicago.
  • You may avail great discounts on your flight tickets to Chicago.
  • Our Travel Curators guide you at every step of booking Chicago flight tickets.
  • We book your journey to Chicago at a pocket-friendly price.
  • We advise you on our cheapest deals and promo codes to fly to Chicago.