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Chicago Flights Deals

Mon, Jul 28 - Wed, Aug 06

Houston to Chicago

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$124 *Per Person

Thu, Aug 14 - Thu, Aug 21

Orlando to Chicago

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$124 *Per Person

Tue, Aug 05 - Tue, Aug 26

Los Angeles to Chicago

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$154 *Per Person

Fri, Aug 15 - Fri, Aug 22

Fort Lauderdale to Chicago

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$172 *Per Person

Fri, Aug 08 - Wed, Aug 20

Miami to Chicago

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$179 *Per Person

Wed, Aug 06 - Thu, Aug 21

Washington to Chicago

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$181 *Per Person

*All fares are in USD. Fares are last updated on Jun 26, 2025 at 09:00 PM. The fares listed above are for flight tickets and include fuel surcharges, service fees and taxes. Please note, these fares are based on historical data and are subject to change without prior notice. Prices cannot be guaranteed at the time of booking. For more details, please review our Terms and Conditions before booking.

Fly to Chicago with Ease – Book with Trips & More More

 

Nestled on the shores of Lake Michigan, Chicago is a gorgeous jewel decked with skyscrapers, world-class museums, and alluring beaches that you cannot resist admiring. If you have been seeking a chance to escape to a destination that lets you dive into music, art, and comedy, then fly to Chicago without further ado. Though the fresh waters of Lake Michigan and the high skylines never fail to beguile you, the heart of the city lies in its diverse neighborhoods that concoct a different story each time you visit there. 

Whether you choose to ride the Ferris Wheel in Navy Pier, sunbathe on its striking beaches, explore several exhibits at its museums, or get acquainted with wildlife in a zoo, this city knows how to keep you hooked. So, all you need to do is book your flights to Chicago with Trips & More More, and pack your bags for a memorable trip.

Book Your Flights to Chicago with Trips & More More


If you have been seeking the right platform to book your plane tickets to Chicago, then stop by the Trips & More More for an amazing flight booking experience. Here’s why you should book with us.

Seamless Booking: Whether you choose to book your airline tickets to Chicago online or by taking the help of our travel experts, Trips & More More travel portal ensures you a seamless booking experience. And, once your tickets are booked with us, you receive instant ticket confirmations with all your booking details.

Exclusive Fares: So, if you are seeking a platform to book an air ticket to Chicago, then look no further. Trips & More more offers you amazing discounts on flight booking, along with a seamless booking experience. However, to enjoy the maximum discounts, book your flights a few weeks in advance.

 Flexible Travel Plans: Trips & More More travel allows you to book, cancel, or reschedule your flights sans any hassle. So, notwithstanding whether it’s economy, first class, or business class flights to Chicago that you are seeking, just go ahead and book them without any hesitation and cancel or reschedule them as and when required, as Trips & More More offers you a flexible booking options (T&C apply).

Airports in Chicago

If you are planning a trip to Chicago, then here is a list of its prominent airports that you need to know about in order to zero in on the right one for you. 

O’Hare International Airport: Being one of the busiest airports in the world, O’Hare International Airport is well-connected to other destinations across the globe. Catering to both domestic and international travelers, it helps you cover more than 200 destinations across 50 countries. You can take direct flights to Chicago to reach here or you can take flights with layovers. United Airlines and American Airlines are among the popular airlines operating here. 

The airport offers amenities like shopping outlets, dining options, lounges, free Wi-Fi, and even yoga rooms. Transport facilities like taxis, buses, trains, and ride-share services are also available there to help you explore the city with ease. 

Midway International Airport: Nestled approx. 12 miles from the Loop business district of the city, Midway International Airport is one of the busiest airports in the U.S. Serving more than 21 million passengers, it helps you travel to 95 destinations across Canada, Mexico, the Caribbean, and the United States.

The airport’s terminal houses a bevy of amenities including retail shops, a lounge, a yoga room, free Wi-Fi, and more to offer you a convenient experience. Besides that, it also provides you with buses, taxis, and shuttle services connecting you to the center of the city.

Chicago DuPage County Airport: Situated approx. 30 miles to the west of downtown, Chicago DuPage County Airport is a vital hub for corporate, private, and charter aviation. Operating around 31 flights across 15 different routes, this airport connects you not only to the cities in the United States but beyond that. Famed for its world-class facilities, when you arrive at this airport whether by taking business class flights to Chicago or Economy, you can enjoy various amenities available at the airport.

Frequently Asked Questions

 What is Chicago known for?

A major hub for commerce, finance, and transportation, Chicago is famed for its diverse cultural scene, distinctive architecture, and delicious cuisine.  If you are planning to fly to Chicago, book your flights with Trips & More More and enjoy amazing discounts and flight deals to Chicago.

What are the most popular airlines flying to Chicago?

United Airlines, Delta Air Lines, and American Airlines are among the popular airlines flying to Chicago. 


 Which is the cheapest month to fly to Chicago?

October and November are the best months to avail cheap flights to Chicago.   

What is the best time to visit Chicago?

The spring season, between April and June makes for the best time to visit Chicago.         

How to find the cheapest flights to Chicago?

Book with Trips & More More to enjoy cheap airline tickets to Chicago. To enjoy the cheapest flights, plan to visit during off-peak season.

What are the top attractions to visit in Chicago?

Navy Pier, Millennium Park, and Buckingham Fountain are some of the top attractions to visit in Chicago. 

What are some family-friendly activities in Chicago?

While traveling with family, you can climb to Skydeck Chicago for panoramic views, visit Lincoln Park Zoo to witness the wildlife, and enjoy fun activities at the Chicago Children’s Museum.  

How many days are recommended for a trip to Chicago?

Though a 3-day trip can help you explore the major attractions, extending it to 5 days can leave you with an insightful experience.   

What are the popular cuisines in Chicago?

Italian Beef, Deep-dish Pizza, and Chicago-style hot dogs are some of the popular cuisines you must try here.   

What places can you visit on a day trip from Chicago?

On a one-day trip from Chicago, you can explore a historic town like Galena, explore nature at Indiana Dunes National Park, or relax by Lake Geneva. 

 

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