Flights from Chicago (MDW) to Guadalajara (GDL) from USD95

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The Lowest Fares from Chicago to Guadalajara

cmp-daily-histogram-bars-legend-min-price-aria-label USD165
cmp-daily-histogram-bars-legend-max-price-aria-label USD478
Displaying fares for November-2026
  • MDW–GDL: cmp-view-offers-disclaimer. Find Offers
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    NOV

  • MDW–GDL, 11/11/2026: From USD192
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  • MDW–GDL, 11/12/2026: From USD226
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  • MDW–GDL, 11/13/2026: From USD205
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  • MDW–GDL, 11/14/2026: From USD216
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  • MDW–GDL, 11/15/2026: From USD195
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  • MDW–GDL, 11/16/2026: From USD216
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  • MDW–GDL, 11/17/2026: From USD248
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  • MDW–GDL, 11/18/2026: From USD248
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  • MDW–GDL: cmp-view-offers-disclaimer. Find Offers
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  • MDW–GDL, 11/20/2026: From USD478
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    21

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  • MDW–GDL, 11/22/2026: From USD309
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  • MDW–GDL, 11/23/2026: From USD270
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    24

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  • MDW–GDL, 11/25/2026: From USD355
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  • MDW–GDL, 11/26/2026: From USD166
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  • MDW–GDL, 11/27/2026: From USD352
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  • MDW–GDL, 11/28/2026: From USD165
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  • MDW–GDL, 11/29/2026: From USD166
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  • MDW–GDL, 11/30/2026: From USD173
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  • MDW–GDL, 12/01/2026: From USD244
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    DEC

  • MDW–GDL, 12/02/2026: From USD192
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  • MDW–GDL, 12/03/2026: From USD414
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  • MDW–GDL, 12/04/2026: From USD418
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    05

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  • MDW–GDL, 12/06/2026: From USD367
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  • MDW–GDL, 12/07/2026: From USD341
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    08

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  • MDW–GDL, 12/09/2026: From USD455
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  • RangeUSD165-USD478

    Book our lowest prices from Chicago to Guadalajara

    USD
    Book our lowest prices from Chicago to Guadalajara
    From
    To
    Fare type
    Dates
    Price
    Chicago (ORD)Guadalajara (GDL)One way
    |
    Economy
    Depart 08/12/2027

    from

    USD133

    Viewed: 8 hours ago

    Chicago (MDW)Guadalajara (GDL)One way
    |
    Economy
    Depart 08/22/2027

    from

    USD172

    Viewed: 10 hours ago

    Look on our website for the price that best suits you.*
    Fly with Volaris from Chicago to Guadalajara

    Fly with Volaris from Chicago to Guadalajara

    Swap skyline views for colorful plazas, and deep-dish pizza for birria tacos. Flying southbound, Volaris’ flights from Chicago to Guadalajara open up an exciting contrast: the fast-paced energy of a global U.S. hub meeting the rhythmic charm of Mexico’s second-largest city. Whether you’re visiting family, discovering your roots, or escaping to warmer days, flights to Guadalajara from Chicago with Volaris are your tickett to a cultural deep-dive with convenience and style.

    Cathedral of Guadalajara and city center streets illuminated at night.

    Preparing for your Chicago to Guadalajara flights means staying organized and informed:

    • Check-in: Check in online via the Volaris app or website 72 hours before your flight to skip airport lines.
    • Documents: Bring a valid passport and, if you're not a Mexican citizen, complete your Forma Migratoria Múltiple (FMM) before arrival.
    • Luggage: Review baggage rules on weight and dimensions for both carry-on and checked bags to avoid surprise fees.
    • Weather in Chicago: Summers are warm and humid, while winters can be snowy and freezing—layer up depending on season.
    • Weather in Guadalajara: Expect a mild, dry climate most of the year. The rainy season runs June through September.
    • Things to do in Chicago before your flight: Treat yourself to skyline views from the Willis Tower or stroll the Riverwalk before heading to O'Hare for departure.
    The wing of a Volaris airbus parked in Guadalajara airport, and another Volaris airbus in the background.

    Guadalajara International Airport (GDL) is located roughly 30 minutes south of downtown. It’s the third busiest airport in Mexico, with modern facilities including currency exchange, SIM card kiosks, and food options.

    Ground transport is plentiful: authorized taxis and app-based rideshare services operate from designated pickup points. If you want freedom to explore nearby towns, car rental in Guadalajara airport is also available right at the terminal. Bus connections are available too, though less direct.

    Once you've landed and dropped your bags, dive into the flavor of Jalisco. Sample tortas ahogadas from a street vendor or settle into one of the best restaurants in Guadalajara like Alcalde or Xokol. If you're arriving late, several hotels near Guadalajara airport offer easy check-in and shuttle service.

    Colorful streets of Tlaquepaque, with Mexican flags hanging from the ceilings and status of spirit animals on the sidewalk.

    Historic, hip, and full of life. Here are five areas and attractions you shouldn't miss:

    Centro Histórico
    Colonial architecture, the grand Teatro Degollado, and the twin-towered cathedral make downtown a visual delight. Don't miss the murals by José Clemente Orozco.

    Tlaquepaque
    This artistic district is known for its colorful streets, mariachi music, and artisan shops. Great place to buy souvenirs and taste local tequila.

    Zapopan
    A more upscale suburb with the famous Basilica of Our Lady of Zapopan, open-air shopping, and family-friendly parks.

    Chapultepec Avenue
    The city's cool corridor: indie bookstores, record shops, modern art galleries, and weekend street fairs fill this youthful district.

    Parque Metropolitano
    If you need a nature break, this huge green space is great for a jog, a picnic, or a pedal boat ride.

    A couple dancing in the streets of Guadalajara, dressed in traditional Mexican outfits.

    Make the most of your visit with this relaxed but diverse three-day plan:

    Day 1: Culture and Cafes

    • Explore the Hospicio Cabañas, a UNESCO site with dramatic Orozco murals.
    • Sip a café de olla in a Centro Histórico coffeehouse.
    • Visit the Museum of Journalism and Graphic Arts.

    Day 2: Markets and Music

    • Walk the Mercado Libertad (San Juan de Dios), one of the largest indoor markets in Latin America.
    • Take a guided mariachi tour in Plaza de los Mariachis.
    • Try pulque or craft beer at a local cantina.

    Day 3: Side Trip and Views

    • Head to the town of Tequila for distillery tours and agave field views.
    • Ride the Teleferico (cable car) in Zapopan for skyline shots.
    • End the night with dinner at a rooftop restaurant in Colonia Americana.
    Matute Remus bridge in the metropolitan area of Jalisco, at sunrise.
    • Book your tickets to Guadalajara from Chicago: at least six weeks in advance for better pricing.
    • Keep a translation app handy if your Spanish is rusty—English is not widely spoken in some areas.
    • Use sunscreen even cloudy days in Guadalajara can come with strong UV exposure.
    • Exchange some cash at the airport for small vendors or public transport.
    • If you're deciding where to stay look for hotels near Guadalajara airport if you have early flights or short stays.