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Exclusive Club Departure
Chicago Getaway
4 Days: Thursday, October 11–Sunday, October 14, 2018

per person double occupancy

*INCLUDES round-trip airfare, fuel surcharge and all air taxes and fees.

view travel itinerary

Why Chicago, you ask? Here’s why: over five thousand restaurants—Chicago was named the “Restaurant City of the Year” by Bon Appétit; 60 local breweries, an award-winning skyline and awesome architecture, 26 miles of lakefront, the 13-block stretch of Michigan Avenue dubbed The Magnificent Mile—home to three indoor malls and 50 flagship stores; 60 museums—see the world’s largest and most complete Tyrannosaurus Rex at The Field Museum; 77 distinct neighborhoods and 500 parks and gardens to explore—including art-filled Millennium Park, where the iconic Cloud Gate sculpture resides. Enjoy three nights in centrally located accommodations and a get-acquainted tour. Don’t miss Chicago Riverwalk for breathtaking views of some of Chicago’s most gorgeous architecture; Navy Pier—with shops, eateries, an IMAX cinema and sightseeing boat tours—and Willis Tower’s Skydeck Chicago—for breathtaking views of the city.

$1,399 per person double occupancy

Call for single and triple reservations. Fuel surcharge, air taxes and fees subject to change. Per person deposit is $600. Additional deposit may be required at time of air ticket purchase.

*After deadline, call 617.338.1111 for availability


  • Round-trip regularly scheduled flights from Boston to Chicago

  • Three nights' four-star accommodations: Hotel Felix (or similar)

  • Breakfast daily

  • Half-day guided panoramic Chicago tour

  • Escorted, private round-trip airport/hotel transfers


Chicago's top 3 classic foods: our hot dog, deep-dish pizza and Italian beef.

  • DEEP-DISH CHICAGO PIZZA: Lou Malnati's Pizzeria, The Original Gino's East of Chicago

  • CHICAGO-STYLE HOT DOGS: Portillo's, George's Hot Dogs or Red Hot Ranch in Bucktown, and Franks 'N' Dawgs or The Wiener's

  • ITALIAN BEEF: Al's Beef in Little Italy, Mr. Beef on Orleans. It's a small space with more of a "dive" vibe

Last updated 1/18/2018 3:42:11 PM

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