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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 Breaks – What to do…
FIRST TIME IN CHICAGO?
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.
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.
- Return flights from the UK
- 4 nights hotel accommodation
Price based on December 2023 departures from Glasgow
Alternative dates and departure airports available
Standard Hotel from £874 pp
Prepare yourself for an memorable experience in the heart of Chicago’s downtown with a stay at the Tremont Chicago Hotel at the Magnificent Mile. The Tremont Chicago offers boutique accommodations with a sleek, contemporary design and décor. The property is ideally located just steps away from the famed shopping, dining and entertainment of Michigan Avenue’s Magnificent Mile. A short 6 minute walk takes you to the beaches and nearby access to public transit CTA service that provides a convenient means to get around.
Superior Hotels from £1093 PP
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 from £1236 pp
The Conrad Chicago is set in Chicago, within 200 yards of Michigan Avenue. This property is situated a short distance from attractions such as Water Tower Chicago. The property is 650 yards from Chicago Museum of Contemporary Art. An American breakfast is available every morning at the hotel. Popular points of interest near the accommodation include Shops at Northbridge, 360 Chicago and Millennium Park.