Fly Direct from Chicago to Monterey County, CA

Fly Direct from Chicago to Monterey County, CA

Book New Nonstop Flights from Chicago to Monterey, CA ✈️

This new nonstop route connects two iconic destinations and makes it easier than ever for Midwest travelers to experience the iconic Monterey Bay Aquarium, the charm of Carmel-by-the-Sea, 99 miles of breathtaking California coastline in Big Sur, legendary Pebble Beach golf and world-class food and wine.

Seasonal nonstop service from Chicago O'Hare International Airport (ORD) to Monterey Regional Airport (MRY) with United Airlines is now open for booking, with weekly Saturday flights through late August,  bringing you straight to California’s magnificent Pacific Coast this summer. If you plan to travel outside the seasonal schedule, MRY also offers connecting flights via major hubs. Book your flight on United.com.

Don't Miss These Highlights

Where to Stay

Accommodations to Fit Every Style of Traveler

When you escape the Midwest heat, settle into accommodations where coastal breezes drift through open windows, and sunsets steal the show. From oceanfront resorts and boutique inns to charming B&Bs and family-friendly hotels, Monterey County’s accommodations offer comfort, character and stunning scenery.

  • Carmel-by-the-Sea: Storybook village, world-class food & wine, charming inns, unique boutiques and stunning natural beauty.
  • Monterey & Cannery Row: Walkable waterfront, aquarium access, coastal dining, family-friendly hotels. 
  • Big Sur: Epic cliffs, redwood hikes and once-in-a-lifetime stays.
  • Pebble Beach: Iconic golf, 17-Mile Drive and world-renowned coastal luxury. 
  • Carmel Valley: Sun-drenched wineries, resort retreats, spas and mountain views.

So Much to See & Do

Adventure, Attractions & Relaxation

Swap Chicago’s skyline for rugged coastline, marine wildlife and scenic drives that feel worlds away from the city. Monterey County’s mild summer weather makes outdoor adventures especially inviting. Cooler coastal temperatures mean comfortable hiking, biking, and exploring all day long.

Where to Eat & Drink

Fresh Seafood, Local Produce & Award-Winning Wines

Leave deep dish behind (just for the week) and indulge in seafood pulled straight from the Pacific and wines grown in nearby vineyards. Taste the best of California’s Central Coast, shaped by ocean bounty, world-class agriculture and award-winning winemakers.

Events

Plan Your Trip Around Something Special

Monterey County’s summer calendar gives Chicago travelers even more reason to book that nonstop flight. From summer live music to prestigious tournaments and cultural celebrations, there’s always something happening along the coast

Fly Direct from Chicago to Monterey County, CA
Fly Direct from Chicago to Monterey County, CA
Fly Direct from Chicago to Monterey County, CA
Fly Direct from Chicago to Monterey County, CA
Fly Direct from Chicago to Monterey County, CA
Fly Direct from Chicago to Monterey County, CA
Fly Direct from Chicago to Monterey County, CA
Fly Direct from Chicago to Monterey County, CA

Monterey Pre-Reunion and Corkscrew Hillclimb

8/8/2026 - 8/9/2026
Recurring daily

Get ready for two thrilling days of historic racing action! Owners of more than 300 historic race cars, most of which are competing days later in the Rolex Monterey Motorsports Reunion, will get valuable track time in a more relaxed and less-crowded environment. This is a great opportunity for fans to get up close to these unique cars and watch...

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Rolex Monterey Motorsports Reunion

8/12/2026 - 8/15/2026

The annual Rolex Monterey Motorsports Reunion is a museum revving to life with hundreds of historic and period-correct race and sports cars from nearly every era. It is one of the world’s most prestigious motorsport lifestyle gatherings. Experience race cars driven as they were originally intended to be driven in a festival environment. Also, see NASCAR legends racing in their...

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Pebble Beach Concours d'Elegance

8/16/2026

The Pebble Beach Concours d’Elegance is the flagship of Pebble Beach Automotive Week. Begun in 1950 and now considered to be the world’s premier celebration of the automobile, this is the ultimate event for every car enthusiast.  Each year, the finest collector cars gather on the 18th fairway of Pebble Beach Golf Links to compete for the title of Best...

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West End Celebration

8/22/2026 - 8/23/2026

Sand City's West End Celebration is a unique, family-friendly event that celebrates community and the diversity of artistic talent found within Monterey County. The streets of the West End District of Sand City come alive with the arts of every genre. Discover innovative art, listen to continuous live music from multiple stages and have the opportunity to purchase works from...

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Monterey Turkish Arts & Culture Festival

8/29/2026 - 8/30/2026

Hosted by the Turkish American Association of California, this festival is a joyful expression of community, friendship and cultural exchange. Whether you’re savoring Turkish delights or admiring handcrafted treasures, you’ll feel the warmth and hospitality that Turkey is known for. Experience the rich and colorful traditions of Turkey through: Mesmerizing Whirling Dervish performances, plus a teaching demo Live Turkish music...

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Monterey County Fair

9/3/2026 - 9/7/2026

Enjoy five unforgettable days of carnival rides, live entertainment, rodeos, motorcycle races, agriculture, shopping, fair food, exhibits, community celebrations, and nonstop family fun. The theme for 2026 is “Cowboy Boots & Coastal Roots”. Fair hours are 11 a.m. to 11 p.m. Thursday through Sunday and 10 a.m. to 11 p.m. on Mondays. Pre-sale tickets are now available online. Ticket prices...

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INDYCAR Grand Prix of Monterey (Season Finale)

9/4/2026 - 9/6/2026
Recurring daily

Join in for high-speed, open-wheel racing, as the world's top single-seaters tackle Laguna Seca's iconic corkscrew turn. The NTT INDYCAR SERIES returns to Monterey at the peak of summer vacation, bringing unmatched intensity and high-speed action to the region’s famously cool, coastal climate. Fans can also kick off race weekend at the Pre-Race Street Party on Alvarado Street in Downtown...

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Festa Italia

9/11/2026 - 9/13/2026
Recurring daily

A beloved, free, family-friendly event offering a full experience of Italian culture. The festival features a diverse range of authentic Italian cuisine, lively music, energetic dancing and a welcoming atmosphere for attendees of all ages. Guests can indulge in a tempting array of Italian dishes available for purchase, from Calamari and Steak and Sausage Sandwiches to Pasta, Arancini and Cannoli,...

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Start Planning Your Chicago to Monterey Getaway

This summer, trade humidity for ocean mist, traffic noise for crashing waves, and city heat for coastal cool. With nonstop flights connecting Chicago to Monterey County, your refreshing California escape is closer than ever. Book your flight, pack a light sweater, and get ready to experience summer the Monterey way.

Fly Direct from Chicago to Monterey County, CA
Fly Direct from Chicago to Monterey County, CA
Fly Direct from Chicago to Monterey County, CA