Chicago Flight Tickets

Book Super Saver Airfares NOW!

  • ROUND-TRIP
  • ONE-WAY
Red Umbrella

Thank you For Your Enquiry.

Expect a call from us in a few minutes

Ok, Got it.

Thank you for your enquiry.

Expect a call from us in a few minutes

Ok, Got it.
  • Unbeatable Packaged Deals Exclusive holiday deals at great-offered prices with Low-Fare Promise.
  • Secure & Transparent Bookings100% secure transactions. Transparent booking terms at no hidden cost.
  • Call Only Offer: Save up to $30 on Unpublished Deals 1-833-914-2482

Chicago flight deals

* Fares on this page are updated as of Jun 21, 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.

  • BOS

    Boston

    Aug 18, 2024
  • ORD

    Chicago

    Aug 23, 2024

$113.67*

Per person inc. Fee

Book Now
  • LAX

    Los Angeles

    Aug 10, 2024
  • CHI

    Chicago

    Aug 13, 2024

$169.18*

Per person inc. Fee

Book Now
  • DEN

    Denver

    Jun 29, 2024
  • CHI

    Chicago

    Jul 01, 2024

$212.97*

Per person inc. Fee

Book Now
  • MIA

    Miami

    Jun 25, 2024
  • ORD

    Chicago

    Jul 20, 2024

$221.18*

Per person inc. Fee

Book Now
  • ACY

    Atlantic City

    Jul 16, 2024
  • ORD

    Chicago

    Jul 31, 2024

$225.16*

Per person inc. Fee

Book Now
  • DCA

    Washington

    Sep 25, 2024
  • ORD

    Chicago

    Oct 01, 2024

$232.96*

Per person inc. Fee

Book Now
  • BNA

    Nashville

    Aug 18, 2024
  • MDW

    Chicago

    Aug 20, 2024

$375.84*

Per person inc. Fee

Book Now
  • EUG

    Eugene

    Aug 06, 2024
  • ORD

    Chicago

    Aug 09, 2024

$415.20*

Per person inc. Fee

Book Now
  • DSM

    Des Moines

    Jul 03, 2024
  • ORD

    Chicago

    Jul 03, 2024

$516.34*

Per person inc. Fee

Book Now
  • SDQ

    Santo Domingo

    Jul 02, 2024
  • ORD

    Chicago

    Jul 07, 2024

$599.56*

Per person inc. Fee

Book Now

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.