Book Flights to Chicago – Explore the Windy City
Plan your Chicago adventure with Travelay™ for easy flight booking, great deals, and seamless access to the City of Big Shoulders.
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Why Visit Chicago
Who is Chicago For?
No Matter Who You Are, You’ll Find Your Vibe
Families
Travelers & Nomads
Professionals
Couples & Romantics
Free Spirits
Travel Smart – Tips for Chicago Flyers
Have a quick look at these must know tips before you pack your bags to Chicago!
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Best Time To VisitOctober-November and April-May -
Insider TipExplore hidden speakeasies in River North. -
Local FavoriteLou Malnati’s deep-dish pizza reigns supreme
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Transportation TipUse the CTA pass for unlimited daily rides
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Your Chicago Adventure Awaits
Have the best experience in the windy city, make the most of your trip by visiting historic places, eating out at the best spots and satisfying your inner shopper!
Magnificent Mile for All-in-one Shopping
Dine in the Famous Billy Goat Tavern and Grill
Explore The Field Museum of Natural History
Flight Tickets To Chicago, Backed By Real People
Be worry free and fly to Chicago with complete trust and transparency with Travelay™!
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No Hidden Fees -
Real Humans,
No bots -
Pay Your Way –
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24/7 Coverage, Any Time Zone
Ready To Feel The Heat
Of Chicago?
Let’s make it happen — search flights online
or talk to your agent today.
