* 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.
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.
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.
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.
Frontier Airlines offers the cheapest airfares to Chicago.
The main airport of Chicago is Chicago O'Hare International Airport, and its nearby airport option is Chicago Midway International Airport.