10 Best Airlines to Fly to Chicago (Updated 2024)

by Jem
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Are you planning to explore the top airlines to Chicago in 2024? We’ve meticulously sifted through data from 150 airports globally to identify airlines that stand out for their competitive pricing, outstanding amenities, and stellar customer feedback. Let’s delve into the details!

Chicago, a city of architectural splendor and diverse culture, is a destination that calls for an exceptional journey. The best airlines to fly to Chicago understand this, offering services that transform your trip into an adventure right from take-off. Whether you’re drawn to its history, its culinary scene, or its vibrant neighborhoods, flying with the right airline enhances your experience.

As you embark on this exploration, it’s not just about arriving in Chicago, but also about how you get there. The airlines we’ve selected excel in comfort, service, and value, ensuring your travel is as remarkable as the city itself. Imagine gliding through the skies in a cocoon of comfort, arriving refreshed and ready to delve into the wonders of Chicago.

This voyage to the Windy City deserves an airline that complements its magnificence. We’ve sifted through countless options, focusing on those that stand out for their excellence in customer satisfaction and quality. These airlines are not just carriers; they’re your first taste of Chicago’s unparalleled charm.

Your Chicago adventure begins the moment you board your flight. With our curated list of the best airlines, you’re assured of a journey that’s as memorable as the destination. Chicago’s allure starts in the skies, setting the stage for an unforgettable experience.

Best Airlines to Fly to Chicago right now

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Now, let’s dive into the 10 best airlines to fly to Chicago in 2024.

1. Delta Airlines

Jet off to Chicago with Delta Airlines, a leader in air travel. Delta transforms your flight into a memorable journey, setting a high bar for comfort and service. Known for its wide network, Delta connects travelers to numerous destinations globally, with Chicago as a key node.

Onboard, Delta stands out with spacious seating and top-notch in-flight entertainment. You’ll find options for every mood, from blockbuster movies to soothing music. For those looking for deals, Delta frequently offers competitive pricing, especially if you book in advance. And for those ready to fly in style, check out Delta One and Delta First Class.

Based in Atlanta, Delta serves as a convenient gateway to Chicago for passengers from various locations. Whether you’re eyeing a luxury experience or a budget-friendly trip, Delta’s range of travel classes caters to all.

Delving into sustainability, Delta’s efforts are commendable, with initiatives aiming to reduce its environmental impact. This commitment adds an extra layer of satisfaction to your travel experience, knowing you’re flying with a responsible carrier.

With Delta, your Chicago adventure begins the moment you board, thanks to its blend of reliability, comfort, and eco-consciousness.

Take departure for Chicago with the industry-leading airline, Delta Airlines.
Take departure for Chicago with the industry-leading airline, Delta Airlines.

2. United Airlines

Imagine soaring to Chicago with United Airlines, an experience that blends luxury and efficiency. United’s expansive network connects travelers to an array of destinations, including major cities across the globe and, of course, the bustling heart of Chicago.

One of the best airlines to Chicago, United stands out with its MileagePlus rewards program, offering great deals for frequent flyers. United’s hubs, notably in Chicago, Denver, and San Francisco, make it a convenient choice for connecting flights to and from the Windy City.

United’s in-flight experience is something to talk about. Expect spacious seating and a variety of entertainment options to make your flight enjoyable. And, if you’re hunting for bargains, keep an eye out for United’s special offers, especially during off-peak seasons.

Whether flying economy or splurging on United’s first class, this airline caters to different budgets without compromising on quality. Plus, their commitment to customer service ensures a smooth and pleasant journey.

In the realm of sustainability, United is making strides, notably with investments in cleaner technology and more sustainable fuels. This conscious effort adds an extra layer of satisfaction to your Chicago-bound journey.

With United Airlines, you’re not just traveling; you’re embarking on the first chapter of your Chicago story.

United, one of the best airlines to fly to Chicago, provides fantastic discounts to regular travelers.
United, one of the best airlines to fly to Chicago, provides fantastic discounts to regular travelers.

3. American Airlines

Embark on a journey to Chicago with American Airlines, where travel is redefined. This airline prides itself on its extensive network, connecting an impressive range of global destinations, including Chicago, a city of limitless wonder.

Step onboard and discover America’s unique blend of comfort and convenience. Spacious seats and a diverse array of in-flight entertainment options ensure a relaxing flight, whether in economy, American Airlines Business Class, or American Airlines First Class. Looking for a great deal? They often surprises with budget-friendly fares, especially when planned in advance.

In the heart of the experience, you’ll find the best airlines to go to Chicago offer more than just a flight. American Airlines leads with its AAdvantage rewards program, making each trip more rewarding. Whether you’re a frequent flyer or an occasional traveler, these perks add a special touch to your journey.

American’s hubs, including Dallas/Fort Worth, Charlotte, and Chicago itself, facilitate easy connections to and from the Windy City. Catering to all travel preferences, the airline offers both luxurious and economic options, ensuring a comfortable journey for every traveler.

Though sustainability efforts are not its primary highlight, American Airlines’ focus on customer satisfaction and network breadth makes it a preferred choice for many. With American Airlines, every flight to Chicago promises to be more than just travel; it’s the beginning of an exciting adventure.

Travel is redefined when you fly with American Airlines to Chicago.
Travel is redefined when you fly with American Airlines to Chicago.

4. JetBlue

JetBlue refreshes the concept of air travel, offering a delightful escape to Chicago. Renowned for its customer-first approach, this airline brings a unique flavor to the skies. Their routes crisscross North America, touching down in major cities, with Chicago being a highlight.

Onboard, JetBlue’s modern, spacious cabins offer a breath of fresh air. The seats are more generous with legroom, and the entertainment options are top-notch, including free WiFi – a rarity in the skies. This focus on passenger comfort sets JetBlue apart.

In terms of pricing, JetBlue strikes a fine balance. While they’re not always the cheapest, they regularly roll out tempting deals. Keep an eye on their offers, and you might snag a budget-friendly ticket to the Windy City.

JetBlue’s hub at New York’s JFK Airport positions it perfectly for those traveling from the East Coast to Chicago. Whether you’re after an affordable economy ticket or a more upscale experience in JetBlue’s Mint class, this airline caters to a wide range of budgets.

JetBlue’s blend of comfort, customer service, and commitment to the environment makes every trip to Chicago an enjoyable and responsible adventure.

INSIDER TIP: Again, I highly recommend signing up for Going.com (Scott’s Cheap Flights) to find the best deals. Last year, I got an email alert on a $459 roundtrip fare from Chicago to London with JetBlue. The premium version is 100% worth the money, but I would at least sign up for the free version to save big on airfare this year.

JetBlue stands apart from other airlines with its exceptional focus on sustainability.
JetBlue stands apart from other airlines with its exceptional focus on sustainability.

5. Southwest Airlines

Welcome aboard Southwest Airlines, where the journey to Chicago is as vibrant as the destination itself. Southwest’s friendly approach and no-frills model have earned it a special place in the hearts of travelers. They fly to a vast array of destinations, making Chicago easily accessible from almost anywhere in the U.S.

Settle into Southwest’s cabin and enjoy the simplicity and comfort they’re known for. While in-flight frills are minimal, the airline’s warm service and efficient operations more than make up for it. It’s the little things, like the two free checked bags, that make Southwest a favorite.

Southwest is also known for its incredible flexibility, offering no change fees, which is a huge plus for spontaneous or uncertain travel plans. This policy, unique among U.S. carriers, adds tremendous value for travelers.

Nestled in their fourth paragraph, a mention of the best airlines to fly into Chicago brings Southwest into focus. With its primary hub at Dallas Love Field, Southwest offers numerous flights to Chicago, catering to both budget-conscious travelers and those seeking convenience without the luxury price tag.

While Southwest may not boast flashy amenities or extensive international routes, its commitment to customer satisfaction and straightforward pricing model make it a top choice for many. This airline proves that sometimes, simplicity is indeed the key to a memorable journey.

Southwest is highlighted in their fourth paragraph, which also includes a list of the top airlines to fly to Chicago.
Southwest is highlighted in their fourth paragraph, which also includes a list of the top airlines to fly to Chicago.

6. Alaska Airlines

Alaska Airlines, known for its picturesque routes and exceptional service, offers a unique way to reach Chicago. With a focus on the U.S. West Coast, Alaska’s network connects a multitude of cities to Chicago, making it a popular choice for travelers seeking a blend of comfort and reliability.

In the second paragraph, it’s clear why Alaska is among the best airlines to fly to Chicago. Their commitment to customer service shines through in every aspect of the journey. With generous legroom and a personal touch in service, Alaska Airlines makes every flight a pleasant experience.

Alaska’s pricing is competitive, often offering deals that are hard to resist. Keep an eye on their promotions for affordable fares to Chicago. Whether you’re looking for a bit of luxury with Alaska Airline First Class, or planning a budget trip, this airline has options for all.

Their main hub in Seattle positions Alaska Airlines as a convenient choice for those flying from the Pacific Northwest and beyond. While they may not have the global reach of some larger airlines, their dedication to quality service on their routes, including to Chicago, stands out.

Alaska Airlines may not be the largest airline, but its focus on creating a warm and welcoming experience for travelers sets it apart. With Alaska, your journey to Chicago begins with scenic views and ends with lasting memories.

It is evident from the second paragraph why Alaska is one of the best airlines to fly to Chicago.
It is evident from the second paragraph why Alaska is one of the best airlines to fly to Chicago.

7. Spirit Airlines

For a lively and affordable trip to Chicago, Spirit Airlines sets the stage. Known for its ultra-low-cost model, Spirit offers some of the most wallet-friendly flights to the Windy City. It’s the go-to airline for savvy travelers keeping an eye on their budget.

Spirit covers a wide range of destinations across the Americas, with Chicago being a key stop. This makes it an ideal choice for those looking to explore the city without breaking the bank. Their simple, no-frills approach means you pay only for what you need.

Onboard, Spirit keeps things basic but comfortable. While amenities are limited to keep costs low, the airline’s efficient service ensures a smooth journey. Frequent sales and promotions make it possible to find even cheaper deals for your Chicago adventure.

Spirit operates primarily from its hubs in Fort Lauderdale and Detroit, offering convenient connections to Chicago. While it’s a budget airline, the value it provides, especially for short-haul trips, is hard to beat.

Flying with Spirit Airlines might be a no-frills experience, but it’s one that promises efficiency and affordability. It’s perfect for those who prioritize practicality and cost-effectiveness on their way to explore the vibrant city of Chicago.

Spirit Airlines offers economical and efficient flights despite their seemingly basic experience.
Spirit Airlines offers economical and efficient flights despite their seemingly basic experience.

8. Frontier Airlines

Frontier Airlines redefines budget travel, offering a cost-effective way to discover Chicago. Known for its economical fares, Frontier is a hit among travelers who prioritize affordability without compromising on the essentials of a good journey.

Frontier’s network, while primarily focused within the U.S., includes several international destinations. With Chicago as a prominent destination, it’s an excellent choice for domestic explorers and international visitors alike. Their straightforward, no-nonsense approach to flying makes travel planning simple and stress-free.

Frontier’s charm lies in its ability to offer low-cost tickets. In the third paragraph, we highlight this as one of the best airlines to go to Chicago for budget-conscious travelers. While amenities on Frontier are basic, the savings on tickets often leave more in your pocket for enjoying Chicago’s attractions.

Operating mainly from its hub in Denver, Frontier is well-positioned for travelers across the country heading to Chicago. While it’s a budget carrier, frequent promotions and deals mean you can often fly for less than you might expect.

Frontier’s commitment to efficient, affordable travel makes it one of the best airlines for those who want to explore Chicago without a hefty price tag. It’s an airline that proves a great travel experience doesn’t have to be expensive.

Frontier Airlines demonstrates that an amazing trip doesn't have to cost a lot of money.
rontier Airlines demonstrates that an amazing trip doesn’t have to cost a lot of money.

9. Allegiant Airlines

Allegiant Airlines offers a streamlined, hassle-free way to experience Chicago. Catering to travelers who appreciate direct routes and no-frills service, Allegiant stands out for its practical approach to air travel. The airline’s focus on smaller, regional airports connects various U.S. cities directly to Chicago.

Allegiant’s flights are predominantly domestic, with a strong presence in smaller markets. This makes it a go-to airline for many looking for direct flights to Chicago from less served cities. Their efficient operations make traveling simpler and often quicker.

In the third paragraph, it’s worth noting Allegiant as one of the best international airlines to Chicago for its unique market niche. While not offering the wide array of amenities found on larger carriers, Allegiant’s commitment to convenient, straightforward travel is its main draw.

Allegiant’s hub at Las Vegas McCarran International Airport, along with several focus cities, provides accessible routes to Chicago. The airline’s pricing model is budget-friendly, with options to add on extras as needed, allowing passengers to customize their travel experience.

Allegiant’s straightforward, no-nonsense approach to air travel makes it an excellent choice for those seeking an uncomplicated and efficient journey to Chicago. It exemplifies that sometimes, simplicity is the ultimate sophistication in travel.

Allegiant is defined by its pragmatic approach to air travel, catering to passengers who value easy routes and simple service.
Allegiant is defined by its pragmatic approach to air travel, catering to passengers who value easy routes and simple service.

10. Hawaiian Airlines

Hawaiian Airlines brings a touch of island charm to your flight to Chicago. Known for its warm hospitality, Hawaiian offers a flight experience infused with the aloha spirit, making every journey a pleasant one. While primarily connecting the Hawaiian Islands to the mainland, Chicago is among its continental destinations.

In the second paragraph, the mention of the best airlines to Chicago fits seamlessly. Hawaiian Airlines stands out for its exceptional in-flight service, which includes island-inspired meals and entertainment. This unique offering sets Hawaiian apart from other carriers and provides a memorable experience for passengers.

Hawaiian’s main hub is in Honolulu, offering travelers a unique opportunity to experience a slice of island life before continuing to Chicago. This dual-destination potential is especially appealing to those seeking a little adventure en route to the Windy City.

The airline caters to a range of budgets, with competitive pricing for its unique service. Regular deals and promotions make it possible to experience Hawaiian’s exceptional service without a hefty price tag.

Flying with Hawaiian Airlines to Chicago isn’t just about getting from point A to B; it’s about enjoying a journey filled with warmth and the unique spirit of the islands. It’s a taste of Hawaii, all the way to the heart of the Midwest.

Hawaiian Airlines, one of the best airlines to fly to Chicago, adds a little island charm.
Hawaiian Airlines, one of the best airlines to fly to Chicago, adds a little island charm.

Frequently Asked Questions (FAQs) About the Best Airlines for Flying to Chicago

Looking for insights on the top flights to Chicago? Below are some frequently asked questions and answers about the best airlines for your Chicago travels.

What month is cheapest to fly to Chicago?

The cheapest month to fly to Chicago is February. This is based on data analysis, which indicates that traveling in February can save you up to 25% compared to the average yearly flight price. It’s also advised to avoid traveling in July, as flight prices during this month can increase by up to 14% compared to the average. Booking your flights in January and February is estimated to yield the cheapest prices, with April and December being other good options for budget-friendly travel. To get the best savings, it’s recommended to book your flight about 3 months in advance, as last-minute bookings can significantly increase the price.

Which is the best airline to fly with?

The best airlines to fly with in 2023, according to Money’s analysis, are:

  • Delta – Best for Reliability
  • Alaska – Best for Pets
  • Southwest – Best for Families
  • American – Best for Rewards
  • JetBlue – Best for Customer Satisfaction

Each of these airlines was chosen for excelling in specific areas, offering a range of options depending on your travel needs and preferences.

What airport is cheaper in Chicago?

Chicago Midway International Airport (MDW) is often a cheaper option for flights compared to Chicago O’Hare International Airport (ORD). This is primarily because Midway is a major hub for Southwest Airlines, which is known for its competitive pricing, especially for domestic flights within the United States. Additionally, flying with Southwest from Midway can often be more economical due to the airline’s policy of not charging for checked baggage. However, it’s important to note that flight prices can vary based on several factors, including the time of booking and the specific flight route.

Discover the top airlines for your trip to Chicago.
Discover the top airlines for your trip to Chicago.

What airline is based in Chicago?

United Airlines is an airline based in Chicago. It is one of the major airlines in the United States and has its headquarters in the Willis Tower in Chicago. United operates a large domestic and international route network, with an extensive presence in the Asia-Pacific region. The airline’s primary hub is at Chicago O’Hare International Airport.

What airline is big in Chicago?

Chicago is a major hub for both United Airlines and American Airlines. United Airlines, headquartered in Chicago, has a significant presence at Chicago O’Hare International Airport (ORD), which is one of its primary hubs. American Airlines also operates a large number of flights from O’Hare, making it another major airline in Chicago. Both airlines offer extensive domestic and international flight networks from this city.

Which is the better airline, United or American?

Determining whether United Airlines or American Airlines is better depends on various factors, including personal preferences, specific travel needs, and individual experiences. Both airlines have strengths and weaknesses:

  • United Airlines is known for its extensive global route network, particularly strong in the Asia-Pacific region, and a significant hub presence in Chicago.
  • American Airlines boasts a large network with a strong presence in domestic and international routes, and is also a major player in Chicago.

Ultimately, the choice between United and American might come down to factors such as specific routes, loyalty programs, customer service experiences, and personal preferences. It’s recommended to consider your own travel requirements and past experiences with these airlines to make the best choice for your needs.

What is the most reliable airline in the US?

As of 2023, Delta Air Lines is often regarded as the most reliable airline in the United States. Delta is known for its high on-time performance and low rates of flight cancellations and mishandled baggage. This reputation for reliability, along with its extensive network and customer service, makes Delta a preferred choice for many travelers. However, it’s important to note that airline performance can vary and is subject to change based on a variety of factors.

Concluding Thoughts on Chicago’s Best Airlines

As we wrap up our exploration of the best airlines for your journey to Chicago, it’s clear that each carrier offers a unique experience tailored to various traveler needs. Whether you’re seeking luxury, budget-friendliness, exceptional service, or direct routes, there’s an airline that fits the bill. From the aloha spirit of Hawaiian Airlines to the budget-friendly approach of Spirit Airlines, you have a plethora of choices for your Chicago adventure.

Remember, the best Chicago airline for you depends on your personal preferences. Luxurious travelers might lean towards Delta’s high-end offerings, while those on a tighter budget might prefer the economical options of Frontier or Spirit Airlines. For those valuing customer service, JetBlue’s commitment to satisfaction stands out.

If you’re planning a trip from within the U.S., consider airlines like Southwest for their flexibility or Alaska Airlines for their exceptional service. International travelers have great options too, with United and American Airlines providing extensive global networks.

When choosing your airline, consider factors like the best flight to Chicago for your schedule, the amenities you value most, and the overall travel experience you desire. Remember, sometimes the journey is as important as the destination. Your choice of airline can set the tone for your entire Chicago experience.

In conclusion, Chicago’s vibrant culture, stunning architecture, and lively atmosphere are just a flight away. With our guide to the best airlines, you’re equipped to make an informed decision for a comfortable, enjoyable, and memorable trip to the Windy City. Here’s to your next great adventure in Chicago!

Best Airlines to Fly to Chicago right now
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