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On Chicago holidays take in the sights, immerse yourself in shopping and sightseeing or hire a car to explore the surrounding areas.
See Chicago’s famous sights and absorb its energy and culture on a city break. Stay at one of our stylish 4 star hotels in great locations for a memorable trip.
Experience an exhilarating blend of history, sightseeing and electric nightlife on Chicago city breaks. Choose from a wide range of excellent hotels and combine with flights for guaranteed savings.
Tailor-make your Chicago holiday by choosing the flight, hotel and experience that suits you.
Holidays in Chicago provide a city break with a difference. Walk along the famous Navy Pier, enjoy stunning views from the 103rd floor of the Skydeck at the Willis Tower, and try a famous local deep-dish or Chicago-style from Gino’s East Pizza.
Stroll along the Navy Pier with its amusements and entertainment, in the summer catching firework displays twice weekly. Then head to the Magnificent Mile for some of Chicago’s best shopping. Take full advantage of this prestigious location on Lake Michigan by hiring a car and venturing to the exclusive River North, with its famed galleries and boutiques or take the family to one of the 24 Chicago beaches. Catch a play in the Theatre District, before retiring to one of our hotels. Or enjoy a romantic meal at the John Hancock observatory, taking in the stunning views, before seeking out the nightlife in the Rush & Division district.
BA Star Rating
BA Star Rating
BA Star Rating
Chicago provides a perfect mix of top-end 5 star hotels, trendy bars and luxurious restaurants, offering a wealth of international cuisines. The Waldorf Astoria, previously the number 1 hotel in the US, offers a huge spa and health club. Spend a cultural city break in Chicago and explore the vast collection of modern American and European art at The Art Institute of Chicago, before enjoying a glass of wine or fruity cocktails in trendy Wicker Park and Bucktown.
Spa hotels provide the ideal remedy for your body and soul, after a day shopping along the Magnificent Mile. For the perfect spa break we recommend The Waldorf Astoria, for its extensive spa and fitness facilities. The Peninsula has been voted ‘America’s healthiest hotel’, and Spa@theWit is renowned for being one of the best spas in Chicago. For a personalised spa experience visit mySpa at Fairmont Chicago, Millennium Park, and if time is precious choose the express lunch manicure.
Enjoy the romance of Chicago, stroll hand in hand along the shores of Lake Michigan, book a table for dinner on the 95th floor John Hancock observatory. See a theatre show at the world famous theatre district, not forgetting to take advantage of a photo opportunity in front of the illuminated lights of the ‘Chicago’ sign. For the perfect ending snuggle up at one of our luxury hotels.
There is plenty to do on Chicago family holidays with a range of family-friendly activities to choose from. Enjoy family time on the sandy beaches, take the kids to see free fireworks at Navy Pier every Wednesday and Saturday throughout the summer. Open their imagination with a visit to the Field Museum to visit the worlds most complete T. rex, ‘Sue’. Then tuck in to a famous local delicacy, the deep-dish pizza.
There are 24 beaches along the Chicago lakefront, our favourites are the popular Oak Street Beach, which has the largest sunbathing area, walking distance from Downtown. See and be seen at North Avenue Beach, for the best city views and amenities. The quieter Montrose Beach is a little further away, but there is plenty of parking if you have hired a car. Ohio Street beach is right next to the famous Navy Pier, it can often feel like you are on your own private beach.
Hire an Economy car on your holiday for an unforgettable road trip.Find deal
Upgrade to an Intermediate car on your fly-drive holiday.Find deal
Hire a people carrier, great for groups with lots of luggage.Find deal