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Book cheap flights to Chicago

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  1. Home / City / Cheap Flights to Chicago

Popular Flight Deals

*Pricing & Availability Notice*

Flight prices and availability displayed on this page are sourced via authorized travel suppliers’ APIs and airline distribution systems. Prices are subject to real-time availability and may change before booking confirmation. Final fares, rules, and conditions are determined by the operating airline.

LGA New York

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ORD Chicago

01 Jan 2026 - 04 Jan 2026

MWA Marion

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ORD Chicago

28 Feb 2026 - 01 Mar 2026

JFK New York

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ORD Chicago

01 Jan 2026 - 04 Jan 2026

HOU Houston

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ORD Chicago

20 Feb 2026 - 23 Feb 2026

FNT Flint

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ORD Chicago

22 Jan 2026 - 25 Jan 2026

PHL Philadelphia

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ORD Chicago

15 Jan 2026 - 18 Jan 2026

LEX Lexington

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ORD Chicago

13 Feb 2026 - 15 Feb 2026

DSM Des Moines

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ORD Chicago

15 Jan 2026 - 22 Jan 2026

Book cheap flights to Chicago

Looking for the best airfares to Chicago? Plane To Paradise™ brings you handpicked, value-packed flight deals that make exploring the Windy City easier and more affordable. Whether it’s a business visit, a family holiday, or a weekend escape, our platform connects you with real-time fares from trusted global suppliers—so you reach Chicago without overspending.

Why Visit Chicago? 

Chicago blends world-class architecture, history, food, art, music, and Midwestern charm. Here’s what awaits you:

  • Iconic Landmarks: Millennium Park, Navy Pier, Willis Tower Skydeck.
  • Cultural Gems: Art Institute of Chicago, Field Museum, Museum of Science & Industry.
  • Music & Nightlife: Blues and jazz clubs, theaters, and Broadway shows.
  • Sports Heaven: Home of the Cubs, Bulls, Blackhawks, and Bears.
  • Food Capital: Deep-dish pizza, Chicago-style hot dogs, fusion dining, Michelin-starred restaurants.
  • Lakefront Escape: Scenic paths, beaches, and waterfront parks along Lake Michigan.

How Plane To Paradise™ Delivers the Best Chicago Deals

Our fares are sourced in real time from accredited travel suppliers and consolidators to ensure:

  •  Competitive Pricing: Access exclusive, value-driven fares.
  •  Transparency: Clear details on baggage, refunds, and fare rules.
  •  More Choices: Economy, Premium Economy, Business & First Class flights.
  •  Secure Ticketing: Bookings issued safely through licensed partners.

Popular Routes to Chicago

  • New York (JFK/LGA/EWR) → Chicago
  • Los Angeles (LAX) → Chicago
  • Miami (MIA/FLL) → Chicago
  • Houston (IAH/HOU) → Chicago
  • International routes from London, Toronto, Frankfurt, Mexico City & more

Why Book With Plane To Paradise™?

  • Independent Platform: We display unbiased flight options.
  • Real-Time Fares: Live pricing based on seat availability.
  • Secure Payments: Safe and verified booking systems.
  • 24/7 Support: Assistance throughout your journey.

Your Chicago Journey Starts Here

From skyline views and iconic museums to sports, music, and legendary food, Chicago promises an unforgettable experience. Book your Chicago flight deal with Plane To Paradise™ and enjoy the perfect balance of value and convenience.

 Search. Compare. Book. Fly. Your Chicago adventure begins here.

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Global Trust Badges & Customer Reviews

With globally accredited trust badges and honest feedback from real travelers, we provide a transparent, reliable, and secure booking experience from start to finish.

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TrustScore 4.2
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Rating 5/5
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Trustscore
100 / 100
P
Google
★★★★★

I flew from Toronto (YYZ) to Delhi (DEL) this past April for my brother’s wedding, and Plane to Paradise made the entire booking experience stress-free. I had been searching on my own without much luck, but their team stepped in with great advice and found me an excellent fare. Everything was organized quickly and handled with care, which gave me real peace of mind before such an important trip. It truly felt like I was in good hands, and I’ll be happy to book with them again in the future.

M
Google
★★★★★

Booked my flight from YYZ TO DEL through plane to paradise and had a great experience. The wait time was minimal and the prices were better as compared to other platforms. Highly recommend!!

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Google
★★★★★

My trip with plane to paradise was an absolute dream! From the first time I contacted them to the moment I got back home, everything was seamless and perfectly organized. The itinerary was well-planned

Rating Disclaimer: Trust scores displayed on this website are collected from independent third-party platforms including Trustpilot, Google Reviews, and ScamAdviser. These ratings reflect publicly available opinions and trust evaluations at the time they were published. We do not claim ownership, guarantee accuracy, or assure outcomes based solely on these external scores. For verified details, please click the respective platform links or reports.

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Disclaimer: Plane To Paradise™ is an independent online flight booking platform owned and operated by Plane To Paradise LLC, a company registered in the State of Pennsylvania, United States (Entity Number: 7570169), with its principal office located at 2706 Victoria Ln, Easton, PA 18045, USA.

Plane To Paradise™ is IATAN-accredited (International Airlines Travel Agent Network), ensuring industry compliance and recognition in the sale of airline tickets and related flight services.

We are not affiliated with, endorsed by, or officially connected to any airline or aviation brand. All flight deals and booking services offered on this website are provided through our network of licensed and authorized airline consolidators and travel suppliers with whom we maintain formal agreements.

Airfares displayed on this website are dynamically sourced in real time and are subject to availability, airline inventory updates, seasonal changes, and market demand. Prices, refund rules, penalties, baggage policies, and other fare conditions are determined by the selected airline at the time of booking. No reservation is guaranteed until ticket issuance or airline confirmation has been completed.

By using this website, you acknowledge that you are purchasing airfare through an independently operated platform, and you accept that all fares, terms, and conditions may change without prior notice. We encourage users to review our full Terms & Conditions before confirming any booking.

For assistance or inquiries, please contact our customer support team.

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