Westchester Holidays
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Top hotels in Westchester
Congress Plaza Hotel
"Fantastic room and location."
Reviewed on 9 Jun, 2026
The Chicago Hotel Collection - Magnificent Mile
"Our room was spacious and very clean"
Reviewed on 8 Jun, 2026
The Chicago Hotel Collection Ambassador Gold Coast
"Honestly during my trip I stayed at 6 Chicago hotels and this one was my favorite along with the Midlan hotel. Both exquisite, don’t forget to check out the roof top! I almost left without seeing the view it gorgeous!"
Reviewed on 8 Jun, 2026
Popular places to visit
Wrigley Field
Chicago’s world-renowned baseball ground, Wrigley Field is an iconic stadium where you can learn about the all-American sport and even catch a game.
Soldier Field
Events center, NFL stadium and historic landmark all in one, this waterfront field is one of Chicago’s most popular destinations.
Naval Base Great Lakes
After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.
What to do in Westchester
Wendella's 90-min Chicago River Architecture Tour
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.
