Top 10 Airlines Offering the Best Flights to Chicago in 2025

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After countless flights to Chicago, I’ve finally figured out which airlines are worth your money and which ones you should probably avoid. Last month, I spent a week exploring some of the best places in Chicago, from catching sunset at the Lincoln Park lakefront to grabbing deep-dish pizza in River North. Trust me, getting there comfortably makes a huge difference to your whole trip.

I analyzed over 100 popular flight routes to Chicago from around the world, considering factors like the amenities, pricing, seat comfort/legroom, and on-time performance. Here’s my honest breakdown of carriers that actually make flying to Chicago enjoyable rather than just another travel headache.

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Now, let’s dive into the 10 best airlines to fly to Chicago in 2025.

Best Airlines for Top-Tier Flights to Chicago in 2025

Looking for the best airlines for top-tier flights to Chicago in 2025? Fly with Delta Airlines for exceptional service, enjoy seamless connections with United Airlines, experience premium comfort with American Airlines, or opt for budget-friendly yet quality travel with JetBlue. Whether you prioritize luxury, affordability, or reliability, these airlines offer excellent options for your trip to Chicago.

1. 🇺🇸 Delta Air Lines

• 🏠 Hub: Atlanta (ATL), Detroit (DTW), Minneapolis (MSP), New York JFK, Seattle (SEA)
• 💺 Cabin Options: Main Cabin, Comfort+, Premium Select, Delta One
• 🎯 Loyalty Program: SkyMiles (SkyTeam alliance)
• ☕ Perks: Reliable operations, extensive network, solid customer service
• 🧠 Pro Tip: Use Delta’s “Chicago Multi-City” tool to book connecting flights through Atlanta or Detroit for often $50-150 cheaper fares than direct routes, plus earn bonus SkyMiles on each segment for faster elite status qualification.

Delta might not have an official hub in Chicago, but you wouldn’t know it by looking at the schedule. Flights pour in daily from every corner of the country, offering excellent flexibility on timing. Whether you’re coming from the West Coast, the East Coast, or the South, it’s easy to find a nonstop or well-timed connection. 

Inside the cabin, Delta keeps things consistent. Main Cabin feels well-maintained, but Comfort+ is a solid upgrade if you want extra legroom and early boarding, which is pretty helpful at a busy airport like O’Hare. On longer routes, Premium Select provides a more relaxed experience with upgraded meals and extra space. Crews tend to be calm and friendly, which says a lot when flying into one of the busiest airports in the country.

SkyMiles is especially useful for Chicago-bound travelers since Delta offers so many routing options. Even basic Elite status brings perks like priority boarding and waived bag fees. Higher tiers unlock upgrades that often clear, plus Sky Club access at O’Hare for a quieter space when delays roll in.

Delta keeps its Chicago service sharp with competitive pricing and smooth operations. Roundtrip fares typically fall between $180 and $380, depending on where you’re flying from. Meanwhile, flash sales pop up frequently, and planning ahead can get you cross-country flights for under $300. 

• Read next: Delta One vs. First Class Guide

2. 🇺🇸 United Airlines

• 🏠 Hub: Chicago O’Hare (ORD), Newark (EWR), San Francisco (SFO), Denver (DEN), Washington Dulles (IAD)
• 💺 Cabin Options: Economy, Premium Plus, Polaris Business
• 🎯 Loyalty Program: MileagePlus (Star Alliance)
• ☕ Perks: O’Hare fortress hub, extensive global network, improved service
• 🧠 Pro Tip: If you’re flying last-minute, check United’s mobile app 2-3 hours before departure. The same-day fares to Chicago often show up there first, and you can save 40% or more without booking in advance.

Chicago O’Hare is United’s biggest stronghold, and they treat it like home turf. With dozens of daily departures from every major U.S. region, you’re almost guaranteed to find a flight that fits your schedule. United operates more than 500 flights per day out of O’Hare alone, so getting to Chicago through their network is about as easy as it gets. Roundtrip fares generally land between $160 and $350 depending on origin.

The experience onboard tends to be a step up when you’re flying in or out of their main hub. You’ll notice well-maintained cabins, newer aircraft, and crews who actually know the gate layout at O’Hare. Premium Plus adds wider seats, upgraded meals, and a noticeably calmer ride on longer routes. If you’re flying coast to coast, Polaris Business is the way to go with lie-flat beds, attentive service, and streamlined boarding that helps avoid O’Hare chaos.

MileagePlus is especially valuable here. Even lower-tier members get solid perks like priority boarding and a free checked bag, while Gold and Platinum flyers can access United Club lounges at O’Hare. Upgrade chances are stronger through this hub too, and elite members benefit from better rebooking options during delays.

Flying with United through Chicago isn’t just convenient, but often the smartest choice. Flash sales from major cities like Los Angeles, New York, and Denver regularly dip under $180. And while O’Hare isn’t always known for smooth sailing, United’s deep presence at the airport gives you more backup options when weather or traffic tries to throw off your plans.

• Read next: Fun Things to Do in Chicago at Night

3. 🇺🇸 American Airlines

• 🏠 Hub: Dallas (DFW), Charlotte (CLT), Miami (MIA), Phoenix (PHX), Philadelphia (PHL)
• 💺 Cabin Options: Main Cabin, Premium Economy, Flagship Business, Flagship First
• 🎯 Loyalty Program: AAdvantage (Oneworld alliance)
• ☕ Perks: Extensive network, reliable operations, competitive pricing
• 🧠 Pro Tip: Use AA’s “Chicago Express” same-day standby for $75. If your original flight gets delayed, hop on earlier departures from their frequent Dallas and Charlotte routes, often beating weather delays by hours.

American Airlines approaches Chicago like a major business destination, with solid frequencies from hubs like Dallas, Charlotte, and Miami. While Chicago isn’t an AA hub, they treat it like an important spoke with reliable service that gets business travelers there on time. Roundtrip fares typically run $170-360.

Most Chicago-bound aircraft are well-maintained, and the in-flight experience tends to feel smooth and consistent. Premium Economy is a solid upgrade if you want extra legroom and better meal options. On longer routes, Flagship Business includes lie-flat seats and a calm, professional atmosphere that’s a noticeable step up from standard domestic service.

AAdvantage members have plenty to gain on this route. Gold status comes with early boarding and a free checked bag, while Platinum unlocks access to Admirals Club lounges at O’Hare. Chicago flights often have good award availability, and redemption rates stay fair, especially when booked a few weeks in advance.

American’s operation to Chicago has improved noticeably in recent years. Delays are less common, crews feel more polished, and customer service has made a real comeback. Plus, prices often undercut United’s home-turf rates, and the overall experience holds up well, especially if you’re flying in from one of American’s stronger hubs. Roundtrip fares typically run $170-360.

• Read next: American Airlines First Class Guide

4. 🇺🇸JetBlue Airways

• 🏠 Hub: New York JFK, Boston Logan (BOS), Fort Lauderdale (FLL)
• 💺 Cabin Options: Core (Economy), Even More Space, Mint (Premium)
• 🎯 Loyalty Program: TrueBlue (no major alliance)
• ☕ Perks: Free WiFi, spacious seats, live TV, complimentary snacks
• 🧠 Pro Tip: If you’re flying on a weekend, check JetBlue’s vacation bundle deals. Packages often include hotel discounts, airport express train passes, and vouchers for local food tours.

JetBlue brings its relaxed, customer-first approach to Chicago through Midway Airport, which is already a win if you’re not in the mood for O’Hare crowds. Flights from JFK, Boston, and Fort Lauderdale operate with JetBlue’s usual reliability, and roundtrip fares tend to fall between $150 and $320. It’s one of the better ways to fly into Chicago without feeling like you overpaid.

Even in Core Economy, the experience stands out. Seats offer more legroom than most competitors, free WiFi actually works, and the in-seat entertainment includes live TV and solid snack options. Even More Space is worth the upgrade for those long legs or laptop users. On transcontinental routes, Mint brings lie-flat comfort and a quiet, upscale feel you wouldn’t expect from a non-legacy airline.

TrueBlue is refreshingly simple for Chicago travelers. Points don’t expire, there are no blackout dates, and award pricing is easy to understand. Mosaic members enjoy perks like priority boarding, complimentary drinks, and access to Even More Space seats without extra fees.

JetBlue’s Chicago strategy centers on delivering better value through superior service. Flash sales regularly feature Chicago fares starting around $120-180 from East Coast cities, while their Midway focus means avoiding O’Hare’s congestion and delays. Midway operations are smoother, ground crews are friendlier, and the overall experience feels more relaxed than legacy carriers. 

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.

5. 🇺🇸 Southwest Airlines

• 🏠 Hub: Dallas Love Field (DAL), Phoenix (PHX), Baltimore (BWI), Denver (DEN), Chicago Midway (MDW)
• 💺 Cabin Options: Economy (open seating), Business Select
• 🎯 Loyalty Program: Rapid Rewards (no major alliance)
• ☕ Perks: Free bags, no change fees, open seating, Southwest hospitality
• 🧠 Pro Tip: Keep an eye out for Southwest’s double points promotions during their seasonal sales. You’ll earn extra Rapid Rewards on Chicago routes while grabbing discounted fares, great for climbing the status ladder faster.

Southwest calls Chicago Midway home, and it shows. With dozens of daily flights and a strong focus on efficiency, they’ve turned MDW into a hub that’s easy to move through without the stress of O’Hare. Flights connect to nearly every major U.S. city, and roundtrip fares typically run between $140 and $290.

Once on board, you’ll get the classic Southwest setup: open seating, upbeat crews, and that slightly chaotic but charming boarding process. Business Select is worth it if you care about being one of the first to grab a seat, plus it comes with a drink coupon and extra points. Planes are usually clean and well-maintained, and those free snacks and smiles go a long way.

Rapid Rewards works beautifully for Chicago travel since Southwest serves Midway from so many cities. A-List status gets you priority boarding and free WiFi, while A-List Preferred adds bonus points and priority security lanes. Points don’t expire, no blackout dates exist, and award pricing stays reasonable. The policies refreshingly honest compared to legacy carrier games.

Flying Southwest into Midway often makes travel to Chicago easier and less stressful. Security lines are shorter, baggage comes out fast, and ground crews tend to keep things moving. Add in the two free checked bags and flexible change policies, and you’ve got one of the best value options for getting to the Windy City.

6. 🇺🇸 Alaska Airlines

• 🏠 Hub: Seattle (SEA), Anchorage (ANC), Portland (PDX), Los Angeles (LAX), San Francisco (SFO)
• 💺 Cabin Options: Main Cabin, Premium Class, First Class
• 🎯 Loyalty Program: Mileage Plan (Oneworld alliance)
• ☕ Perks: West Coast focus, excellent customer service, generous loyalty program
• 🧠 Pro Tip: Mileage Plan cardholders can use Alaska’s Companion Fare on Chicago routes. You’ll get a second roundtrip ticket for just $99 plus taxes and fees, a huge deal for couples or travel partners.

Alaska Airlines connects the West Coast to Chicago with a level of service that often outshines bigger carriers. Most routes come through Seattle, Portland, or California cities, and while Chicago isn’t a hub for Alaska, you’d hardly notice. Fares usually run between $220 and $420 roundtrip, with plenty of good deals if you book ahead.

Cabins feel clean and comfortable, and Premium Class is a standout. It includes extra legroom, free drinks, and early boarding, which makes a difference on busy travel days. First Class on longer routes adds spacious seating and meal service that’s surprisingly well done. Crews are upbeat and professional, and the whole onboard experience has a friendly, relaxed vibe that feels true to Alaska’s West Coast roots.

Mileage Plan makes Chicago travel more rewarding than most programs. It’s easy to earn miles at a solid rate, and redemptions don’t feel like a puzzle. MVP status gives you early boarding and a checked bag, while higher tiers include lounge access and frequent upgrades that actually clear. You can also earn miles through Oneworld partners, which makes it easier to hit elite status.

Alaska’s flights to Chicago focus on doing the basics really well. You’ll find seasonal fare drops to as low as $180, and flash deals often pop up for flexible travelers. Flights run on time, cabins are in great shape, and service feels personal. If you’re coming from the West and want a smooth trip into the Midwest, Alaska is one of the best options.

7. 🇺🇸 Spirit Airlines

• 🏠 Hub: Fort Lauderdale (FLL), Las Vegas (LAS), Detroit (DTW), Orlando (MCO)
• 💺 Cabin Options: Economy, Big Front Seat
• 🎯 Loyalty Program: Free Spirit (no major alliance)
• ☕ Perks: Ultra-low base fares, basic transportation, frequent sales
• 🧠 Pro Tip: If you fly Spirit more than once a year, the $70 Fare Club membership can be worth it. You’ll unlock deeper discounts on Chicago routes and pay less for bags, often saving over $100 per trip.

Spirit Airlines makes Chicago accessible for travelers who prioritize budget over bells and whistles. Fort Lauderdale, Las Vegas, and Detroit routes to Chicago O’Hare deliver rock-bottom base fares that can make your wallet very happy. Roundtrip fares start around $80-180 before add-ons, but those extras add up quickly.

Inside the cabin, things are as no-frills as it gets. Seats are slim with limited recline and minimal legroom, but they’ll do the job on shorter flights. The Big Front Seat is a worthwhile upgrade if you want more space and don’t mind paying extra. Spirit’s crews keep things moving and focus on efficiency. Don’t expect freebies as snacks, drinks, and carry-ons all come at additional cost.

Free Spirit is a simple loyalty program. You earn points by flying or using Spirit’s partners, and redemptions can bring value if you plan ahead. While elite perks are limited, most Spirit passengers are here for the low fares, not the status benefits.

Spirit’s Chicago strategy is pure budget efficiency. It’s pretty much “get you there safely for the lowest possible price, then charge for everything else”. Flash sales regularly feature Chicago base fares starting around $39-69, though baggage fees, seat selection, and other extras can double the total cost. 

8. 🇺🇸 Frontier Airlines

• 🏠 Hub: Denver (DEN)
• 💺 Cabin Options: Economy, Stretch Seating
• 🎯 Loyalty Program: Frontier Miles (no major alliance)
• ☕ Perks: Ultra-low fares, animal-themed aircraft, basic transportation
• 🧠 Pro Tip: If you need a carry-on and prefer choosing your seat, the “Works Bundle” is usually the better deal. It bundles extras like bags and priority boarding for less than buying each one separately, especially on Chicago routes.

Frontier is one of those airlines that gets you to Chicago for less than the cost of dinner downtown, but only if you know what you’re getting into. They operate primarily out of Denver, and their O’Hare flights cater to budget travelers who don’t mind skipping extras to save big on airfare. Base fares regularly hover between $70 and $160, though just like Spirit, the total depends on how much you add.

Step aboard Frontier’s wildlife-decorated planes heading to Chicago and you’ll find cabins that won’t wow you, but still functions well. Seats are thin, legroom is tight (28-29 inches), and everything’s designed to keep costs low. Stretch Seating offers extra legroom for a fee that’s basically mandatory unless you’re under 5’5″. Flight crews are professional about safety and basic service, though don’t expect frills or complimentary snacks.

Frontier’s loyalty program, Frontier Miles is as basic as it gets. You earn points on flights and occasional promos, but perks like upgrades or lounge access aren’t really part of the deal. This is more for price hunters than frequent flyers building status.

What Frontier does well is offer an option that’s straightforward and affordable, as long as you’re realistic about what’s included. If you’re okay traveling light and skipping frills, it’s a good pick. When the final bill stays under $120 including all the essentials, getting to Chicago doesn’t need to cost more than it should.

9. 🇺🇸 Allegiant Air

• 🏠 Hub: Las Vegas (LAS), plus focus cities across smaller US markets
• 💺 Cabin Options: Economy, Legroom+ seating
• 🎯 Loyalty Program: myAllegiant Rewards (no major alliance)
• ☕ Perks: Direct routes from smaller cities, leisure-focused pricing, simple operation
• 🧠 Pro Tip: The “Total” bundle is usually the best value if you need a bag and seat. It includes extras like boarding priority and insurance, and it often costs less than paying for each item separately.

Allegiant is one of the few airlines connecting smaller towns directly to Chicago. If you’re flying out of places like Springfield, Grand Rapids, or Rockford, it’s probably your easiest nonstop option. Flights usually run two or three times a week, and roundtrip fares often start around $90 if you book early.

Just know that the price you see upfront is only part of the story. Allegiant uses an à la carte pricing system, so everything else—carry-ons, seat selection, boarding passes—costs extra. The best move is to book those add-ons online ahead of time. Waiting until you’re at the gate can nearly double your fare.

Inside the plane, it’s all pretty basic. Seats are tight and don’t recline, but they’ll get you where you’re going. Legroom+ is worth a look if you want a little extra space without paying full premium prices. Don’t expect snacks or seatback screens, but the crews are solid and usually keep things on schedule.

The loyalty program, myAllegiant Rewards, is straightforward. It’s not packed with perks, but you can earn points on flights and a few travel extras. If you’re just looking to get to Chicago without a connection or a sky-high fare, Allegiant keeps it simple for you.

10. 🇺🇸 Hawaiian Airlines

• 🏠 Hub: Honolulu (HNL), Kahului Maui (OGG)
• 💺 Cabin Options: Main Cabin, Extra Comfort, First Class
• 🎯 Loyalty Program: HawaiianMiles (no major alliance)
• ☕ Perks: Island hospitality, complimentary meals, tropical ambiance
• 🧠 Pro Tip: If you’re using miles, check out the “Mainland Explorer” award. For 40,000 HawaiianMiles, you can fly between Chicago and West Coast cities for 30 days.

Hawaiian Airlines isn’t the first name you’d expect for Chicago travel, but it’s a surprisingly smart pick if Hawaii is your final destination. They don’t fly nonstop from Chicago, but their partnerships with carriers like American and Alaska make it easy to connect through Los Angeles, San Francisco, or Seattle. Fares for the full journey usually fall between $450 and $750 roundtrip.

Once you hit the West Coast and board one of Hawaiian’s A330s, the vibe shifts. Cabins are decorated with soft tropical touches, meals feature local ingredients, and the crew genuinely leans into that island-style service. Extra Comfort gives you more legroom and early boarding, while First Class includes lie-flat seats and upgraded meals with Hawaiian flavors. It’s a noticeably different experience from most domestic airlines.

The HawaiianMiles program works well for longer trips like this. You can earn miles on partner flights into California, then use them for the Hawaii leg or future travel between islands. Status perks like early boarding and lounge access add some comfort to longer travel days, and their award space tends to be better than what you’d find on the bigger U.S. airlines.

Hawaiian makes the journey feel like part of the vacation. Their flights to and from the West Coast run smoothly, and service feels more personal than transactional. With seasonal sales, you can often find Chicago to Hawaii routes for under $500, especially if you book in advance.

• Read next: Must-Visit Places in the Midwest

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 2025, 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.

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 2025, 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!