Nonstop Flights: Chicago to Venice $483 r/t [September-October] – American Airlines / Finnair
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Visit our website for example booking dates and more details.
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https://escape.flights/?p=50135

#Chicago

Nonstop Flights: Chicago to/from Miami $139 r/t [April-May] – American Airlines / United
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Visit our website for example booking dates and more details.
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https://escape.flights/?p=50174

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Nonstop Flights: Seattle to/from Chicago $117 r/t [April-May] – Alaska Airlines
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Visit our website for example booking dates and more details.
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https://escape.flights/?p=50180

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Nonstop Flights: Chicago to/from West Palm Beach, Seattle, Baltimore, or Memphis $95-$157 r/t [April-May] (No Fridays or Sundays) – United / American Airlines / Alaska Airlines
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Visit our website for example booking dates and more details.
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https://escape.flights/?p=50214

#Chicago

Nonstop Flights: Chicago to/from Portland, Oregon $179-$188 r/t [April-June] – Alaska Airlines / United
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Visit our website for example booking dates and more details.
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https://escape.flights/?p=50217

#Chicago

Cheap Flights: Chicago to/from Maui-Kahului, Hawaii $382-$388 r/t [April-May] – American Airlines / United
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Visit our website for example booking dates and more details.
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https://escape.flights/?p=50260

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Cheap Flights: Chicago to/from Key West $196-$229 r/t [April-July] – American Airlines
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Visit our website for example booking dates and more details.
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https://escape.flights/?p=50269

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Nonstop Flights: Chicago to/from Dallas $139-$147 r/t [April-May] – American Airlines / United
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Visit our website for example booking dates and more details.
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https://escape.flights/?p=50276

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Nonstop Flights: Chicago to/from Philadelphia $119-$126 r/t [April-May] – United / American Airlines
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Visit our website for example booking dates and more details.
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https://escape.flights/?p=50279

#Chicago

Nonstop Flights: Chicago to/from Punta Cana, Dominican Republic $281-$316 r/t [April-May] – United
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Visit our website for example booking dates and more details.
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https://escape.flights/?p=50289

#Chicago

Nonstop Flights: Chicago to/from New York, Atlanta, Pittsburgh, Denver, Seattle, or Memphis $99-$137 r/t [April-May] (Mostly midweek) – Delta / United / American Airlines
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Visit our website for example booking dates and more details.
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https://escape.flights/?p=50361

#Chicago

Cheap Flights: Milwaukee to Tokyo $851 r/t [April-May] – American Airlines
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Visit our website for example booking dates and more details.
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https://escape.flights/?p=50379

#Chicago

Nonstop Flights: Chicago to/from Miami or Baltimore $119-$139 r/t [May] (Tue, Wed, Sat) – United / American Airlines
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Visit our website for example booking dates and more details.
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https://escape.flights/?p=50390

#Chicago

Nonstop Flights: Chicago to/from Tampa or Fort Myers $139 r/t [May-June] – United / American Airlines
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Visit our website for example booking dates and more details.
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https://escape.flights/?p=50393

#Chicago

Nonstop Flights: Chicago to/from Kansas City, Detroit, or Cleveland $91-$98 r/t [Apr-Jun, Aug-Nov] (No Thanksgiving) – American Airlines / United
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Visit our website for example booking dates and more details.
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https://escape.flights/?p=50401

#Chicago

Nonstop Flights: Chicago to/from Vancouver $362 r/t [April-June] – Air Canada
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Visit our website for example booking dates and more details.
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https://escape.flights/?p=50408

#Chicago

Cheap Flights: Chicago to Singapore $856-$888 r/t [Apr, Sep-Oct] – Cathay Pacific
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Visit our website for example booking dates and more details.
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https://escape.flights/?p=50411

#Chicago

Nonstop Flights: Chicago to/from Puerto Vallarta $402 r/t [April] (Mostly weekdays) – American Airlines / United
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Visit our website for example booking dates and more details.
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https://escape.flights/?p=50423

#Chicago

Cheap Flights: Chicago to Saint Kitts $418-$421 r/t [April-May] – American Airlines
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Visit our website for example booking dates and more details.
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https://escape.flights/?p=50463

#Chicago

(Via our sister publication, Escape Flights - LAX)

Nonstop Flights: Los Angeles to/from Tokyo $428 r/t [late-April] – ZIPAIR Tokyo
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This may be worth paying for a flight into LAX to then catch the flight into NRT. Either arrive the day before or give yourself about 4-hours of connection time when planning the repositioning flight.
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https://escape.flights/?p=50490