9 Best Airlines to Fly to Chicago in 2026 (After Spirit’s Shutdown)

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After dozens of flights into Chicago, both O’Hare and Midway, I’ve got strong opinions on which airlines are worth booking and which ones waste your time and money. I spent a week in Chicago recently and the trip reminded me that a smooth flight sets the tone for everything that follows, from Lincoln Park sunsets to deep-dish in River North. The airline landscape has shifted a lot heading into 2026, so this list reflects what I’d book right now.

I looked at pricing, seat comfort, on-time performance, loyalty programs, and overall experience across more than 100 routes into Chicago. Spirit is gone, Alaska and Hawaiian have merged, and Southwest looks completely different than it did a year ago. Here’s my honest take on the best airlines to fly to Chicago in 2026.

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At a Glance: 9 Airlines Compared

Airline	Hub	Loyalty Program
Delta Air Lines	Atlanta (ATL)	SkyMiles
United Airlines	Chicago O’Hare (ORD)	MileagePlus
American Airlines	Dallas (DFW)	AAdvantage
JetBlue Airways	New York JFK	TrueBlue
Southwest Airlines	Dallas Love Field (DAL)	Rapid Rewards
Alaska Airlines	Seattle (SEA)	Atmos Rewards
Frontier Airlines	Denver (DEN)	Frontier Miles
Allegiant Air	Las Vegas (LAS)	myAllegiant Rewards
Hawaiian Airlines	Honolulu (HNL)	Atmos Rewards

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: Basic, Choice, Choice Preferred, Choice Extra (with standard, preferred, and extra legroom seats)
• 🎯 Loyalty Program: Rapid Rewards (no major alliance)
• ☕ Perks: No change fees, Companion Pass, complimentary snacks and drinks, Chicago Midway hub
• 🧠 Pro Tip: Booking with Rapid Rewards points lets you cancel anytime and get all your points back instantly. No fees, no penalties.

Southwest treats Chicago Midway as a full hub, with dozens of daily flights connecting to nearly every major U.S. city. If you prefer avoiding O’Hare’s chaos, Midway is smaller, faster through security, and closer to downtown. Roundtrip fares typically run between $140 and $290, and flash sales drop even lower if you’re flexible on dates.

Southwest looks different in 2026 than it did a year ago. They moved to assigned seating in January 2026, replacing the old A/B/C open boarding system entirely. You now pick your seat at booking on most fares. They also ended the “Bags Fly Free” policy in May 2025, and checked bags now cost $45 for the first and $55 for the second on standard fares. Choice Extra and A-List Preferred members still get two free bags, and Rapid Rewards cardholders get one.

What keeps Southwest on this list is the flexibility. No change fees is still a major advantage over every legacy carrier, and Rapid Rewards points never expire with no blackout dates. The Companion Pass is also one of the best perks in all of travel. Earn 135,000 qualifying points in a calendar year and your designated person flies with you for just taxes and fees (from $5.60 one-way) for the rest of that year plus the entire next calendar year. For anyone making regular trips to Chicago, that adds up fast.

6. 🇺🇸 Alaska Airlines

• 🏠 Hub: Seattle (SEA), Los Angeles (LAX), San Francisco (SFO), Portland (PDX), Anchorage (ANC)
• 💺 Cabin Options: Main Cabin, Premium Class, First Class
• 🎯 Loyalty Program: Atmos Rewards (oneworld alliance, shared with Hawaiian Airlines)
• ☕ Perks: West Coast hub strength, excellent customer service, generous loyalty program, seamless Hawaiian connections
• 🧠 Pro Tip: Atmos Rewards cardholders can use Alaska’s Companion Fare on Chicago routes. You get a second roundtrip ticket for just $99 plus taxes and fees, which is a massive deal for couples or travel partners.

Alaska Airlines connects the West Coast to Chicago with a level of service that regularly beats the bigger carriers on the same routes. Most flights come through Seattle, Portland, San Francisco, or Los Angeles, and fares usually run between $220 and $420 roundtrip with plenty of deals if you book ahead. Alaska doesn’t hub in Chicago but the frequency and reliability make it feel like they do.

Cabins are clean and comfortable, and Premium Class is a standout with extra legroom, free drinks, and early boarding that helps on busy travel days. First Class on longer routes adds spacious seating and a meal service that’s well above what you’d expect on a domestic flight. Crews are professional and friendly, and the overall experience has a relaxed West Coast feel that I appreciate after years of flying legacy carriers.

Atmos Rewards replaced the old Mileage Plan in late 2025 when Alaska and Hawaiian merged under a single FAA certificate. The combined program covers both airlines and all oneworld partners in one account, and you can choose to earn points by distance, price paid, or segments flown. MVP status gets you early boarding and a free checked bag, while higher tiers include lounge access and upgrades that clear regularly. The Companion Fare alone makes the Alaska Visa card worth holding if you fly to Chicago even once a year.

7. 🇺🇸 Frontier Airlines

• 🏠 Hub: Denver (DEN), plus focus cities at Chicago O’Hare and Midway
• 💺 Cabin Options: Economy, Stretch Seating
• 🎯 Loyalty Program: Frontier Miles (no major alliance)
• ☕ Perks: Ultra-low base fares, frequent Chicago sales, animal-themed planes
• 🧠 Pro Tip: The Works Bundle (bag, seat selection, priority boarding) almost always costs less than buying each add-on separately. Grab it at booking if you need a carry-on.

Spirit Airlines ceased all operations on May 2, 2026, after filing for bankruptcy twice and failing to secure a federal bailout. If you were a Spirit flyer for cheap Chicago routes, Frontier is the closest replacement and already has solid coverage at both O’Hare and Midway. Base fares regularly sit between $70 and $160 roundtrip, and they run flash sales to Chicago that drop as low as $39 one-way.

The experience on board is straightforward budget flying. Seats are thin with tight legroom (28-29 inches), and everything beyond your personal item costs extra. Stretch Seating adds a few more inches of space and is worth the upcharge on anything over two hours. Crews are efficient and professional, and the planes are newer than you might expect for an ultra-low-cost carrier.

Frontier Miles is basic but functional. You earn points on flights and occasional promos, and redemptions work fine if you plan ahead. This is not a loyalty program for status chasers. It’s for people who want the cheapest possible fare and are willing to travel light. If you used to fly Spirit into Chicago, Frontier is the natural replacement with similar pricing and the same no-frills approach.

8. 🇺🇸 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.

9. 🇺🇸 Hawaiian Airlines

• 🏠 Hub: Honolulu (HNL), Kahului Maui (OGG)
• 💺 Cabin Options: Main Cabin, Extra Comfort, First Class
• 🎯 Loyalty Program: Atmos Rewards (oneworld alliance, shared with Alaska Airlines)
• ☕ Perks: Island hospitality, complimentary meals, lie-flat First Class on long-haul routes, seamless Alaska connections
• 🧠 Pro Tip: Book your full itinerary through alaskaair.com or the Alaska/Hawaiian app. Since both airlines now share one booking system, you can manage your Chicago-to-Hawaii connection in a single reservation with one confirmation number.

Hawaiian Airlines is not a typical pick for a Chicago list, but it belongs here if Hawaii is your final destination. Hawaiian and Alaska now operate under a single FAA certificate (granted October 2025), and as of April 2026 they share one booking system with all flights carrying AS codes. Hawaiian also officially joined the oneworld alliance on April 22, 2026. The practical upside is that connecting from Chicago through Seattle, Los Angeles, or San Francisco on Alaska to a Hawaiian long-haul is now seamless. Fares for the full journey usually fall between $450 and $750 roundtrip.

Once you’re on a Hawaiian A330 for the West Coast to Hawaii leg, the experience is noticeably different from standard domestic flying. Cabins have a distinct Hawaiian feel, meals include local ingredients, and the crew leans into that island hospitality without it feeling forced. Extra Comfort gets you more legroom and early boarding, while First Class includes lie-flat seats and upgraded meals. I’d recommend it for anyone doing the long haul to Honolulu or the neighbor islands.

Atmos Rewards is the combined loyalty program that replaced both Mileage Plan and HawaiianMiles in late 2025. You earn points across both Alaska and Hawaiian flights in one account, and you can choose to earn by distance traveled, price paid, or segments flown. Status perks like early boarding and lounge access now apply across both carriers and all oneworld partners, which gives you far more flexibility than the old HawaiianMiles program did. With seasonal sales, Chicago-to-Hawaii routes regularly dip under $500 if you book in advance.

• Read next: Must-Visit Places in the Midwest