Chicago City Break

From£874 Per Person
  • 4 nights Chicago
  • Based on departing Jan 2024
  • Departing from London 
  • Alternative hotels available
  • Alternative durations available
  • Standard Hotel from £690
  • Superior Hotel from £1014
  • Deluxe Hotel from £1111


  • Details
  • Standard Hotels
  • Superior Hotels
  • Deluxe Hotels
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Chicago City Break

Welcome to our Chicago City Break! Chicago, the city that feels like home. Chicago has a little something for everyone. You can visit world-class museums, dine at one of the many Michelin-star restaurants or catch a show in one of over 200 theatres. No matter what you love to do, you’ll feel right at home doing it here.

There are plenty of things to do in Chicago, including tours, spectator sports, shopping and other attractions. Our nightlife doesn’t stop either with plenty of bars and nightclubs, live music and comedy clubs. No matter your budget, you’ll find a hotel to match so start planning your visit today!


Chicago City Break           Chicago City Break


Chicago City Breaks – What to do…



On our Chicago City Break, you’ll fit right in, whatever you love to do. To make the most of your inaugural visit, add these must-see attractions and events to your itinerary.


Millennium Park on a Chicago City Break

If it’s your first time in Chicago, you need to visit our top tourist attraction, the Millennium Park campus. It’s the site of one of the city’s most famous pieces of public art and best-loved selfie darlings, Cloud Gate (aka “The Bean”). The reflective surface has drawn people to the park since 2006, but there’s so much more to see and do.

Splash around in the virtual reality world of Crown Fountain, which features the faces of more than 1,000 Chicagoans spouting at you. Rock climb and skate the ribbon in Maggie Daley Park. Take a photo with the lions in front of the Art Institute of Chicago, where you can easily spend the rest of the day browsing one of the most impressive art collections in the world. Wander south to Grant Park, where Buckingham Fountain’s dramatic water shows sync light, music and action every 20 minutes. And don’t forget to stroll Chicago’s nearby lakefront.


Waterway Cruises on a Chicago City Break

Some of the best views of Chicago are from the water — the Chicago River and Lake Michigan. Whether you want to learn more about the city’s history, get the inside scoop on Chicago’s rich architectural legacy, watch the fireworks display at Navy Pier, or simply kick back and take in the sights, use this guide to help you pick the best boat tour for you.

While you’re out and about, soak up the atmosphere at Chicago’s award-winning Riverwalk. With public art, restaurants, special events and even kayaking, it’s an unmissable part of the Chicago experience.


The Theatre Scene on a Chicago City Break

Chicago is bursting at the seams with theatrical talent. Broadway in Chicago and a slew of Tony Award winning companies bring in big names and blockbuster shows, while more than 200 storefront, experimental and neighbourhood theatre bring you the cutting-edge of contemporary performances.

Chicago is also a city that loves to laugh — after all, Chicago invented improvisation comedy. See where Tina Fey, Stephen Colbert and Steve Carell performed at world-famous The Second City, and take in improv genius at iO and ComedySportz. if stand-up comedy is your thing, grab your tickets for The Laugh Factory or Zanies.


Chicago-style Eats

Come on, you know you want to try it! Deep dish pizza, Italian beef sandwiches and Chicago-style hot dogs are recognized around the world. No, we don’t eat this way all the time, but it’s a great way to indulge on your visit — and immerse yourself in a little iconic Chicago food culture. From Portillo’s to Lou Malnati’s, forget all about your calorie count for a while.


Award-winning Dining on a Chicago City Break

The James Beard Awards gala is held in Chicago in May, and we have our fair share of award winners to back it up. The city also boasts 25 Michelin-starred restaurants, including the world’s only brewpub with a Michelin star (Band of Bohemia).


Skyscraper Experiences on a Chicago City Break

Are you a daredevil? Then go up to the 104th floor and step out onto The Ledge at SkyDeck, a glass box that extends four feet from the Willis Tower facade. For more stunning views, go north to 360CHICAGO at 875 N Michigan (formerly the John Hancock Building). Try out TILT, a glass pane that tilts you out over the city from 96 floors up.

Here’s a hot tip: If you want to try both attractions (and skip the lines), grab a CityPASS Chicago. You’ll also gain access to the Field Museum of Natural History, Shedd Aquarium, Adler Planetarium, Art Institute of Chicago and Museum of Science & Industry for a huge discount.


Tours of the City

Touring Chicago’s waterways is breath-taking, but there are so many other ways to experience the city. Try different modes of transportation, like bikes, buses or segway. History buffs will love the city’s storied past, and there are all kinds of tours for food and beer experiences.

We highly recommend the free Chicago Greeter service, where volunteer locals will walk you through their favourite spots. Scheduled tours throughout the summer will take you on tours through Millennium Park and different Chicago neighbourhoods. And you can choose which neighbourhood you want to see and language you want the tour conducted in with advance notice.


Shop, Shop, Shop on a Chicago City Break

The Magnificent Mile is one of Chicago’s most famous shopping districts, and you’ll find flagship stores — from high street favourites to haute couture legends — along the stretch of shops. Nearby, wander along State Street, where you can visit the original Marshall Field’s, now Macy’s.

For boutique shopping, head to Chicago’s 77 neighbourhoods, where you’ll find unique, one-of-a-kind items you simply won’t want to leave without.

Chicago Summer Festivals


From music festivals (many of which are free), to food festivals and craft beer festivals, Chicago is a city that pulses with activity throughout the year, and especially over the summer months.



The Art Institute of Chicago houses the largest collection of Impressionist and Post-Impressionist art outside the Louvre. Chicago’s Museum of Science & Industry is the largest science museum in the Western Hemisphere (stand in the midst of a tornado, climb into a U-boat, explore a mine — and that’s just for starters). The Field Museum is home to Titanosaur, the largest dinosaur to roam the Earth. Feed sharks, encounter penguins and be a Trainer for a Day at The Shedd Aquarium, as you overlook the waters of Lake Michigan.View the stars (and even sleep under them) at the lakefront Adler Planetarium. And that’s just the beginning.

Price Includes

  • Return flights from the UK
  • 4 nights hotel accommodation



Price based on December 2023 departures from Glasgow

Alternative dates and departure airports available


Standard Hotels

Standard Hotel from £690 pp

Welcome to Staypineapple Chicago, An Iconic Hotel, a dazzling gem amidst a city renowned for its remarkable cuisine, art, architecture, and shopping. Encased in a National Historic Landmark building, this award-winning hotel serves as your perfect gateway to explore the vibrant heart of downtown Chicago.

Nestled ideally in The Loop, with The Theatre District and Millennium Park within an arm’s reach, you are positioned to seize everything the city bestows. Admire the masterpieces at the Art Institute of Chicago, delight in the luxury boutiques of the Magnificent Mile, be awestruck by the intricate details of the Rookery, or join the enthusiastic crowds at the city’s many festive events. After a day of exploration, return to the upscale comforts and deluxe amenities at Staypineapple Chicago. Our hotel exemplifies unmatched style, elegance, and hospitality. Experience Chicago with Staypineapple, where the city’s heart beats the loudest.

Superior Hotels

Superior Hotels from  £1014 PP

Chicago City Breaks - the Viceroy Hotel
Viceroy Hotel



Viceroy Chicago, located in the exclusive Gold Coast neighbourhood, marks Viceroy’s first destination in the Windy City. Located at the site of the 1920s-era Cedar Hotel, among historic mansions and just steps to the Magnificent Mile and Lake Michigan, Viceroy Chicago offers a locally-inspired luxury experience with 180 guestrooms and suites.

Deluxe Hotels

Deluxe Hotels from £1111 pp

Immerse yourself in the sculptural grandeur of The Gwen, a Luxury Collection Hotel, where Chicago’s 1930s glamour fuses seamlessly with modern sophistication. The Gwen captivates with a rich calendar of on-site events and festivities, reflective of every changing season. The striking Art Deco façade, a testament to Gwen Lux, a pioneering sculptress and one of the few women in her field, encapsulates her fearless journey in an era of gender stereotypes.

Located centrally within the historic McGraw-Hill Building, The Gwen stands as a shimmering jewel amid Michigan Avenue’s radiant skyline, offering awe-inspiring vistas and a location second to none. Beyond the city’s hustle and bustle, the interior of this illustrious landmark spellbinds its visitors. Come and experience why The Gwen is continually celebrated as the premier hotel in Chicago, standing shoulder to shoulder with the world’s most prestigious establishments.

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