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Chicago

The Windy City

Overview

Chicago is the ultimate American city, welcoming visitors to a one-of-a-kind experience. Stroll the downtown streets of one of the most walkable cities in the U.S. and explore block after block of outstanding architecture that makes up Chicago’s breathtaking skyline.

Spend the day browsing the diverse galleries of world-class museums, shopping in Chicago’s trendy retail districts and discovering unique attractions along the cool, blue Lake Michigan waterfront. In the evening, dine at a delicious award-winning restaurant, cheer a performance by a cutting-edge theatre company and listen to live music in venues that keep Chicago jumping seven nights a week.

Whether you come for a longer tour of Illinois or indulge in a Chicago city break, the windy city guarantees to blow you away.

Things to do

Holidays

Browse our amazing range of holidays in Chicago

  • Allegro Chicago Hotel

    Allegro Chicago - Kimpton

    from £54

    The charming Allegro Hotel has a wonderful sense of old-world glamour as well as a perfect location in the heart of downtown Chicago.

    Rooms ...see more

  • Public Hotel Chicago

    Public Chicago

    from £44

    Public is a smart and sophisticated hotel located to the north of downtown, in the exclusive Gold Coast district close to excellent shopping, dining and ...see more

  • Ritz Carlton, Chicago

    Ritz Carlton Chicago

    from £102

    Perched at the top of Water Tower Place, an upscale shopping mall, the classy Ritz-Carlton Hotel enjoy fabulous views and a fantastic location in the heart ...see more

  • deep south driving holiday

    Blues & Booze: Chicago to New Orleans

    from £875

    Commencing in the ‘Windy City’ of Chicago, America's third-largest city, head south and experience the tastes and sounds of this exciting part of the USA. ...see more

  • Route 66 driving tour

    Historic Route 66

    from £805

    Starting in Chicago, this classic tour follows the famous Route 66, passing through St Louis and its famous Gateway Arch, Springfield (recognised as the ...see more

Top tips

Top tips for visiting Chicago

1. Exploring the city

• One of the best ways to explore the city’s landmarks is with the Chicago Architecture Foundation which offers more than 90 tours via bus, tram, boat, bike, train, Segway or on foot.
• One of the most popular tours is the Architecture River Cruise aboard the Chicago’s First Lady, which highlights more than 50 architectural gems along the Chicago River.


2. Leave room in your bags

• Discover hundreds of designer and top department stores along Michigan Avenue’s Magnificent Mile and State Street.
• If it’s hip boutiques and vintage shops you’re after then head for Lincoln Park and Wicker Park.
• Alternatively, head out to the suburbs for incredible deals at the outlet centres. The Fashion Outlets of Chicago, based in Rosemont, offers a Shop & Shuttle service to/from Chicago Downtown hotels.


3. Work up an appetite

• With a long list of celebrity chefs and award winning restaurants, food is nearly as hotly contested as sports in Chicago.
• The Chicago hot dog and pizza are a must-try when you visit, but so are the innovative restaurants that are turning out the creative cuisine for which Chicago has become known. With 19 Michelin starred restaurants, there is a great choice in the fine dining scene.
• If you’re dining on a budget, the Bib Gourmand recognises restaurants that are great value as well as great tasting


4. Sports fans

• Chicago is a major sports city! In the spring and summer, Chicago’s two Major League Baseball teams play on opposite sides of the city. Hear the crack of the baseball bat as the Chicago Cubs play at historic Wrigley Field or watch the Chicago White Sox at U.S. Cellular Field.
• In autumn, watch the Chicago Bears play American football in Soldier Field. Winter is the time to experience the nonstop thrills of Chicago Bulls basketball and Chicago Blackhawks hockey, both played at the United Center.


5. Nightlife

• Chicago’s exciting nightlife scene pulses every night of the week.
• Chicago is the only city in the U.S. with five regional Tony Award-winning theatre companies.
• Watch an award-winning Broadway play presented in the classic theatre in downtown district or see a show at one of the city’s cutting-edge theatres.
• Catch a rising comic star at the renowned Second City or sing the blues at Buddy Guy’s Legends bar.


6. Chicago Greeter

• See the city from a local perspective on a private Chicago Greeter tour. This free programme is run by local volunteers who will customise a tour based on your interests.
• They offer 40 tour ideas that include everything from Chicago history to exploring the city’s ethnic neighbourhoods
• Register 10 days in advance for the customised tours. http://chicagogreeter.com/


7. Top music festivals in Grant Park

• The Chicago Blues Festival is the largest blues festival in the world and remains the largest of Chicago’s Music Festivals. You can catch this free event during the month of June.
• If you are a jazz lover, head down to the Chicago Jazz Festival which takes place in September. This free event regularly draws top names from the jazz world.
• If you are into alternative, hip hop and pop then Lollapalooza Festival is for you. With more than 100 bands from music legends across the globe, this is an extraordinary 3-day event.


8. Frank Lloyd Wright

• Famed architect Frank Lloyd Wright developed his signature prairie-style architecture in Oak Park, 10 miles west of Chicago, where he lived and worked during the late 1800s.
• Oak Park is easily accessible from downtown Chicago via CTA’s Green Line train. Take a guided or self-guided tour of the area and get an inside look at the home and studio of America’s acclaimed architect.


Gallery

At a glance


  • On the shores of Lake Michigan
  • Award winning restaurants, theatre and music

Trusted travel partner


Winner of British Travel Awards 2020 - Gold award for Best Holiday Company to Canada (Large)
Winner of British Travel Awards 2020

Gold award for Best Holiday Company to Canada (Large)


Fully protected - We are members of ATOL, ABTA and IATA
Fully Protected

ATOL, ABTA and IATA logos

We are members of ATOL, ABTA and IATA.

Price Match Guarantee
Price Match Guarantee

If you find the same tour cheaper through another operator, we'll match the price.

Why book with American Affair


  • Expert Knowledge
  • 20 Years Travel Experience
  • ATOL & IATA Protected
  • Tailor Made Holidays

Enquire Today

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American Affair Travel Expert

020 7616 9949

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At a glance


  • On the shores of Lake Michigan
  • Award winning restaurants, theatre and music

Trusted travel partner


Winner of British Travel Awards 2020 - Gold award for Best Holiday Company to Canada (Large)
Winner of British Travel Awards 2020

Gold award for Best Holiday Company to Canada (Large)


Fully protected - We are members of ATOL, ABTA and IATA
Fully Protected

ATOL, ABTA and IATA logos

We are members of ATOL, ABTA and IATA.

Price Match Guarantee
Price Match Guarantee

If you find the same tour cheaper through another operator, we'll match the price.

Why book with American Affair


  • Expert Knowledge
  • 20 Years Travel Experience
  • ATOL & IATA Protected
  • Tailor Made Holidays

Get in touch

Stay connected with
American Affair