Cheap round trip flights to Chicago from New York in May 2026 are easier to snag than you might think, especially if you’re planning ahead. Picture this: you’re craving that deep-dish pizza, the stunning skyline views from the Willis Tower, or just a quick escape from the Big Apple’s hustle. May hits that sweet spot—spring in full bloom, mild weather (think 60-70°F days), and fewer crowds than summer peaks. But with demand rising for events and warmer vibes, those ticket prices can climb if you wait too long. Don’t worry, though—I’ve dug into the trends, and right now, round-trip deals hover around $100-$200, sometimes dipping lower with budget carriers. Let’s break down how to land the best ones without breaking the bank.
Why May 2026 Is a Smart Time for Cheap Round Trip Flights to Chicago from New York
May stands out as one of the more popular months for this route, but it’s not the absolute peak like July or August. Weather-wise, Chicago shakes off winter’s chill, with blooming parks and outdoor patios calling your name. It’s shoulder season magic: airlines still release competitive fares to fill seats before summer rushes in.
Have you ever noticed how flight prices feel like a rollercoaster? In May 2026, expect averages starting from about $147 on major carriers like United, American, or Delta for nonstop options. Budget players like Spirit, Frontier, and Southwest often undercut that, pushing round-trips as low as $80-$120 if you play your cards right. Compared to winter lows (January often sees even cheaper deals), May trades rock-bottom prices for better experiences—no snow delays, vibrant city energy, and events that make the trip worthwhile.
The key? Flexibility. Midweek flights (Tuesday or Wednesday departures) frequently shave off $20-$50 compared to weekends. And since May 2026 includes Memorial Day weekend toward the end, book early to avoid those holiday spikes.
Top Airlines Offering Cheap Round Trip Flights to Chicago from New York in May 2026
Multiple airlines compete fiercely on this high-traffic route, which keeps prices accessible. Nonstop flights take about 2-3 hours, making it ideal for a quick getaway.
- Budget Airlines Like Spirit, Frontier, and Southwest — These are your go-to for the lowest fares. Spirit and Frontier often advertise one-way legs under $50, leading to round-trips in the $100 range. Southwest shines with two free checked bags and no change fees—perfect if your plans might shift. Watch for sales; they drop prices further in spring.
- Legacy Carriers: United, American, and Delta — For reliability and perks, these dominate. United (from Newark EWR to O’Hare ORD) and American (LaGuardia LGA to ORD) offer frequent nonstops. Delta from JFK or LGA adds solid service. Expect $147+ round-trip baselines, but loyalty programs or bundles can trim costs.
- JetBlue — A comfy middle ground with free Wi-Fi, snacks, and legroom. Their fares from JFK or EWR often compete well, especially if you value extras over bare-bones budgets.
Pro tip: Check multiple airports—New York has JFK, LGA, and EWR; Chicago has ORD and MDW (Midway, Southwest’s hub). Flying into Midway can save big with Southwest deals.
Best Strategies to Find Cheap Round Trip Flights to Chicago from New York in May 2026
Scoring deals isn’t luck—it’s strategy. Here’s how savvy travelers lock in savings:
Book at the Right Time
Aim for 1-3 months in advance for domestic routes like this. For May 2026, that means starting your search now (early 2026) or by late winter. Data shows prices often bottom out 4-8 weeks out, but waiting too long risks hikes. Mondays or Tuesdays are prime booking days—airlines refresh deals midweek.
Use Tools and Alerts
Set price alerts on Google Flights, Kayak, or Skyscanner. These track fluctuations and notify you of drops. Flexible dates? Use their calendars to spot cheapest weeks in May.
Be Flexible with Dates and Airports
Avoid Memorial Day weekend (late May) if possible—prices jump. Opt for early or mid-May for calmer vibes and lower fares. Midweek round-trips often beat weekend ones by double digits.
Consider Budget vs. Comfort Trade-offs
Ultra-low-cost carriers charge for bags, seats, and changes—factor that in. If you’re packing light, Spirit or Frontier wins. For peace of mind, Southwest or JetBlue might cost a bit more upfront but save headaches.
Look for Error Fares and Sales
Airlines occasionally glitch or promo-drop fares. Follow deal sites or airline newsletters for flash sales targeting this route.
What to Expect Price-Wise for Cheap Round Trip Flights to Chicago from New York in May 2026
Current snapshots show round-trips from $100-$200, with lows around $80-$120 on budget options and $147+ on legacies. One-ways dip to $40-$60. These are estimates—prices shift daily based on demand, fuel costs, and events. May’s popularity means fares trend higher than January but lower than summer. Always compare total costs, including fees.
Top Things to Do in Chicago Once You Land with Your Cheap Round Trip Flights
With cheap round trip flights to Chicago from New York in May 2026 secured, dive into the city. May’s mild weather is perfect for exploring.
Iconic Attractions
Hit Millennium Park for “The Bean,” Navy Pier for lakefront fun, and the Art Institute for world-class exhibits. Walk the Magnificent Mile for shopping and people-watching.
Food Scene
Deep-dish at Lou Malnati’s or Pequod’s? Check. Chicago-style hot dogs? Absolutely. May brings food fests like Windy City Hot Dog Fest.
Events and Festivals
Catch Belmont-Sheffield Music Fest, Do Division Street Fest, or Sueños Music Festival for Latin beats in Grant Park. Lincoln Park Mayfest kicks off summer vibes with music and vendors.
Outdoor Adventures
Rent a bike along the Lakefront Trail or picnic in Grant Park. Boat tours on Lake Michigan offer epic skyline views.
Chicago’s neighborhoods buzz—Wicker Park for street art, Logan Square for breweries.
Packing and Travel Tips for Your Trip
Pack layers—mornings can be cool, afternoons warm. Comfortable shoes for walking are a must. Download the CTA app for trains/buses from airports. Arrive early for security; ORD is busy.
Conclusion: Grab Those Cheap Round Trip Flights to Chicago from New York in May 2026 Today
Wrapping it up, cheap round trip flights to Chicago from New York in May 2026 offer fantastic value—affordable fares, pleasant weather, and a city bursting with energy. By booking smart (early, flexible, tools), choosing the right airline, and planning around events, you’ll save cash for more deep-dish and skyline adventures. Don’t let prices creep up—start searching now and turn that dream weekend (or longer) into reality. Chicago’s waiting—what are you waiting for?
Here are three high-authority external links for more flight deals and info:
- Check current deals on Google Flights
- Compare options at Kayak
- Explore routes on Expedia
FAQs
1. How much do cheap round trip flights to Chicago from New York in May 2026 typically cost?
Expect $100-$200 round-trip, with budget airlines like Spirit or Frontier often under $150. Legacy carriers start around $147. Prices vary by date, airport, and booking timing—midweek is usually cheapest.
2. Which airlines offer the best deals on cheap round trip flights to Chicago from New York in May 2026?
Spirit, Frontier, and Southwest frequently have the lowest fares. United, American, Delta, and JetBlue provide reliable nonstops with perks. Compare on aggregators for the best match.
3. When is the best time to book cheap round trip flights to Chicago from New York in May 2026?
Book 1-3 months ahead, ideally midweek. Set alerts now for drops. Avoid waiting until closer to May, especially near Memorial Day.
4. Are there nonstop options for cheap round trip flights to Chicago from New York in May 2026?
Yes—most flights are nonstop (2-3 hours). From EWR, LGA, or JFK to ORD or MDW. Budget carriers often use Midway for savings.
5. What events make May 2026 great for cheap round trip flights to Chicago from New York?
Festivals like Sueños Music Festival, Belmont-Sheffield, and Do Division add fun. Mild weather and blooming parks enhance the trip without summer crowds.
