11 Cheapest International Destinations to Fly from Chicago in 2025

By AirTrackBot • Posted Feb 09, 2025

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Chicago is one of the most important aviation hubs in the U.S., offering hundreds of international routes with both direct and connecting flights. The city is home to two major airports: O’Hare International Airport (ORD) — among the busiest in the world — and Midway International Airport (MDW), which primarily serves low-cost carriers and regional flights. With fierce competition among airlines, travelers can often find budget-friendly fares to destinations across the globe.

To help you plan your next adventure, we’ve compiled a list of the 11 cheapest international destinations to fly to from Chicago in 2025. From short weekend getaways to long-haul adventures, there’s something here for every budget and travel style.

#1. Calgary, Canada

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Calgary blends modern urban life with the natural beauty of the Canadian Rockies. In the heart of downtown, cultural landmarks like Studio Bell, home to Canada's National Music Centre, and the Glenbow Museum, showcasing Indigenous history and Western Canadian heritage, await exploration. Culinary enthusiasts can savor Alberta's renowned beef at premier steakhouses or sample craft beers at local breweries.

As one of the short international flights from Chicago, Calgary is both an accessible and budget-friendly destination. Airlines such as United Airlines and Air Canada offer direct flights from O’Hare International Airport (ORD), with an average flight duration of approximately 3 hours and 45 minutes. With competitive pricing and frequent departures, securing an affordable roundtrip ticket is convenient.

Cheapest Months to Fly: January, April, October

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#2. Guadalajara, Mexico

Photo: Illya Petrichenko

Guadalajara, the capital of Jalisco, is a cultural gem known for its mariachi music, colonial architecture, and flavorful cuisine. Iconic landmarks like the Instituto Cultural Cabañas, a UNESCO World Heritage site, highlight the city's deep artistic roots. The historic center is lined with grand cathedrals and plazas, while Tlaquepaque charms visitors with artisan markets, vibrant galleries, and traditional Mexican cantinas.

Travelers can fly to Guadalajara (GDL) from both O’Hare (ORD) and Midway (MDW), with multiple airlines serving this route. Aeroméxico, Volaris, and VivaAerobus frequently feature budget-friendly fares, with roundtrip tickets often starting below $200. Seasonal discounts and special promotions further position Guadalajara as one of the most affordable international getaways from Chicago.

Cheapest Months to Fly: February, May, September

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#3. Cancún, Mexico

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With its crystal-clear waters, white-sand beaches, and lively nightlife, Cancún is a dream destination for sun-seekers and adventure lovers alike. While its all-inclusive resorts are a major draw, there’s more to explore beyond the hotel zone. Wander through the Mayan ruins of El Rey, take a boat ride to Isla Mujeres, or swim in cenotes, the region’s famous natural sinkholes. For those who crave vibrant nightlife, Cancún’s clubs and beach bars offer some of the best parties in the Caribbean.

Nonstop flights to Cancún (CUN) are widely available from Chicago’s O’Hare (ORD) and Midway (MDW) airports, with several airlines competing on this popular route. American, United, Spirit, Frontier, and Southwest frequently launch fare sales, making it easy to find an affordable ticket.

Cheapest Months to Fly: March, September, November

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#4. Toronto, Canada

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Toronto, Canada's largest city, offers a dynamic blend of cultural attractions, diverse neighborhoods, and culinary delights. Visitors can explore the iconic CN Tower, stroll through the historic Distillery District, or enjoy a performance in the Entertainment District. The city's multicultural landscape ensures a rich tapestry of experiences for all travelers.

For Chicagoans seeking a quick international getaway, Toronto is an ideal choice. Direct flights from O’Hare International Airport to Toronto Pearson International Airport (YYZ) are available through carriers such as Air Canada, American Airlines, and United Airlines. The flight duration is approximately 1 hour and 30 minutes, making it one of the shortest international flights from Chicago.

Cheapest Months to Fly: April, August, October

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#5. San José, Costa Rica

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San José, the lively capital of Costa Rica, blends urban energy with easy access to the country’s stunning natural wonders. Stroll through bustling markets like Mercado Central, visit cultural landmarks, or explore the city's vibrant arts scene. Just beyond San José, travelers can venture into Monteverde’s cloud forests, hike near Arenal Volcano, or relax on pristine Pacific beaches.

Costa Rica stands out as one of the cheapest countries to fly to from Chicago, combining affordability with breathtaking scenery. Roundtrip fares to San José frequently hover around $250, with United, American, and Spirit Airlines operating both direct and connecting flights. The strong competition on this route helps keep ticket prices low throughout the year.

Cheapest Months to Fly: January, September, November

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#6. Montego Bay, Jamaica

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Montego Bay is renowned for its pristine white-sand beaches, vibrant reggae culture, and flavorful Jamaican cuisine. Visitors can unwind at Doctor’s Cave Beach or explore the lively Hip Strip, known for its array of bars, clubs, and duty-free shops. For those seeking adventure, nearby attractions include Dunn’s River Falls and exhilarating zipline tours through lush rainforests.

Flights from Chicago to Montego Bay (MBJ) are available from O’Hare (ORD) and Midway (MDW), with airlines like American, Spirit, and Southwest operating on this route. Roundtrip fares often start at $235, with lower prices frequently available outside peak holiday seasons.

Cheapest Months to Fly: February, June, October

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#7. Bogotá, Colombia

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Bogotá, Colombia's high-altitude capital, seamlessly blends historic charm with modern vibrancy. Begin your exploration in La Candelaria, the city's historic center, where colonial architecture and the renowned Gold Museum await. For panoramic city views, ascend Monserrate via cable car. Culinary enthusiasts can savor local specialties like ajiaco soup and freshly brewed coffee from nearby highland plantations.

Several airlines connect Chicago to Bogotá, with flights departing from O’Hare and Midway. Carriers such as Avianca, American Airlines, and Spirit frequently run routes to Colombia’s capital, with roundtrip fares starting at $240. While booking in advance often helps secure lower fares, last-minute deals to Bogotá can also appear, especially within a month of departure when airlines adjust prices to fill remaining seats.

Cheapest Months to Fly: March, May, November

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#8. Reykjavík, Iceland

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Reykjavík, the world’s northernmost capital, blends small-town charm with access to some of Iceland’s most stunning landscapes. Wander through the city’s colorful streets, admire its thriving street art scene, or relax in a cozy Nordic café. Just outside the capital, the Golden Circle route takes visitors to Þingvellir National Park, Strokkur Geyser, and the powerful Gullfoss Waterfall. In the winter months, Reykjavík becomes a prime location for witnessing the northern lights, a once-in-a-lifetime experience.

Flights to Reykjavík (KEF) from Chicago (ORD) include both direct and connecting options. Icelandair operates non-stop routes, while budget airline PLAY offers cheaper fares with a layover. The lowest-priced tickets are typically available outside peak travel seasons, with roundtrip fares often starting around $400.

Cheapest Months to Fly: January, February, October

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#9. Nassau, The Bahamas

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Nassau, the lively capital of The Bahamas, is known for its white-sand beaches, turquoise waters, and vibrant island culture. The city’s colorful colonial buildings, historic Fort Charlotte, and bustling markets offer plenty to explore. Along the coast, beachside stalls serve fresh conch salad, while boat tours and snorkeling trips showcase the beauty of the surrounding waters.

For those looking to experience the nightlife, Paradise Island is home to casinos and beachfront clubs. American, Delta, and United operate flights from O’Hare to Nassau, with cheap flights from ORD regularly appearing during lower-demand travel periods.

Cheapest Months to Fly: January, September, November

Roundtrip Flights:

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#10. Paris, France

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Paris captivates visitors with its timeless architecture, world-class art, and vibrant café culture. Landmarks such as the Eiffel Tower and Notre-Dame Cathedral showcase the city's rich history, while the Louvre Museum houses an unparalleled collection of artworks. Districts like Le Marais and Montmartre are bustling with boutiques, galleries, and brasseries serving classic French cuisine.

Paris remains one of the most accessible European destinations from Chicago, with frequent flight options at competitive prices. Major carriers such as Air France, Air Canada, and United operate regular routes to Charles de Gaulle Airport (CDG), providing convenient transatlantic connections.

Cheapest Months to Fly: January, March, November

Roundtrip Flights:

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#11. London, England

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London seamlessly blends centuries of history with modern flair, making it a top destination for those seeking arts, culture, and global cuisine. Iconic landmarks such as the Tower of London and Buckingham Palace offer glimpses into the city's storied past, while neighborhoods like Shoreditch buzz with street art and unique nightlife. The West End theater district boasts a plethora of hit musicals and dramatic performances, catering to theater enthusiasts.

Flights from Chicago (ORD) to London (LHR) are widely available, with British Airways, American Airlines, and United operating direct routes. Ticket prices fluctuate based on demand, but deals under $500 are common, particularly during off-peak travel periods.

Cheapest Months to Fly: February, April, October

Roundtrip Flights:

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Conclusion

As you can see, Chicago offers a wide range of affordable international destinations, from quick getaways to transatlantic adventures. Whether you're looking for a short-haul escape or a long-haul journey, these 11 cheapest international flights from Chicago should provide plenty of inspiration for your next trip.

Before booking your tickets, set up fare alerts with the AirTrack Telegram bot, which will notify you as soon as prices change. A little planning goes a long way in securing a budget-friendly trip to some of the world’s most exciting cities. Happy travels!

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