Chicago your way

There's something for everyone in Chicago. Take your pick from these suggestions to build your best trip.


Catch a taxi or train from O'Hare Airport to your accommodation, a journey of 40 to 50 minutes. We recommend staying in the Loop, River North or Streeterville (also called Magnificent Mile). After a quick refresh, head out to get your bearings.

Things to do when you first arrive:

  • Stroll around Millennium Park, a green space between the Loop and Monroe Harbour. Check out the Jay Pritzker Pavilion, designed by Frank Gehry; Cloud Gate, which looks like a huge chrome bean; Crown Fountain, a captivating video sculpture; and the beautiful Lurie Garden.
  • To mark your first night in Chicago, find the House of Blues Chicago for New Orleans style soul food and fantastic live music. Try the Voodoo Shrimp, Gumbo or BBQ brisket tacos.
1Hop-on hop-off day1 day

A HoHo (hop on, hop off) double-decker bus tour gets your first complete day in Chicago off to a flying start. The city is flat, so it's good to get an elevated view of all the big landmarks. Buy a one-day ticket, with or without the Centennial Wheel.

  • Ascend the Skydeck for amazing 'glass box' views right under your feet. Another high place for a panorama is the John Hancock Tower - 360° views all the way to three other states, plus a thrill ride called the Tilt, which is 96 floors up!
  • Eat a brownie at Palmer House; the recipe was originally created way back in 1893.
  • Stroll the Chicago Riverwalk to the McCormick Bridgehouse & Chicago River Museum. See the huge gearing system that makes the bridge move.
  • Finish the day at Navy Pier, to ride the Centennial Wheel and follow your nose to a pizza, burgers, shrimp or platter of low-and-slow BBQ cuts.
    2Art and architecture day1 day

    Chicago deserves a double A rating for art and architecture. From the restored Wrigley Building to eccentric public art pieces, you can't help but be impressed by the sheer brilliance of the creators.

    • Huge public art installations are sprinkled throughout the CBD (known as The Loop), enabling a scavenger hunt of the artistic kind. You'll find The Picasso, a cubist masterpiece; The Four Seasons, a mosaic depicting the human life cycle; Agora, a big bunch of legs and feet; Monument with Standing Beast, which beckons you inside for a look; and the unforgettable Cloud Gate, a giant stainless steel bean-shaped installation.
    • To give you an expert's understanding of the buildings, the Chicago Architecture Foundation runs guided architectural tours of the city. One option involves a 75-minute boat cruise along the Chicago River. It's a Chicago must-do.
    • Park Grill, alongside Cloud Gate, offers award-winning contemporary American cuisine with a Chicago twist. It's a great spot for lunch, between art and architecture adventures.
    • Millennium Park is where you'll find the Art Institute of Chicago. This is your place for the Old Masters, as well as an entire room of Monet paintings.
    • Finish the day with a Broadway show at CIBC Theatre. Opened in 1906, this ornate theatre was the first Chicago venue to cost more than a million dollars. All the big shows play here.
      3Fun and games day1 day

      If you're travelling with children, or you're a child at heart, this day promises to be a huge hit - especially if you score tickets for a baseball or football game.

      • Adler Planetarium has a collection of unique scientific instruments and hosts the Doane Observatory, which you can visit any morning.
      • The Field Museum is an amazing science museum with exhibitions about dinosaurs, mummies and bugs. Great for kids and adults alike.
      • Chicago is famous for its deep-dish pizzas. One great example is Pizzeria Uno, which has been around for 70 years. Order the Numero Uno; it comes fully-loaded.
      • From a sports point of view, baseball and NFL football are the games to catch in Chicago. In spring and summer head for Wrigley Field, home of the Chicago Cubs baseball team. In autumn, the NFL season kicks off at Soldier Field next to Lake Michigan.
        4Neighbourhood day1 day

        The people who made Chicago great came from a multitude of cultures and countries. For support and comfort as they built new lives, they claimed neighbourhoods of the city as their own.

        • Lincoln Square is where German immigrants settled down. Today many of the restaurants and bars in this neighbourhood serve traditional German-style food and beer.
        • Pilsen is Spanish, and it's also very hip and happening. Here you can enjoy tapas, street art, galleries, vintage shops and the colourful National Museum of Mexican Art.
        • West Town is Polish and La Villita is Latino. The rest are pretty obvious - Greek Town, Chinatown and Little Italy. Visiting these places is like taking a holiday within your holiday.
        • For more insight into the cultural background of Chicago, visit the Chicago History Museum.
        • Close to the museum is Twin Anchors Restaurant, where you can tuck into Chicago's most famous rack of ribs.
        • After dinner, laugh until it hurts at Second City - the comedy club where Bill Murray started his career.
          5Shop 'til you drop day1 day

          In the words of one experienced shopper: "There's no better US city to spend your money in than Chicago". Whether you want to chase an outlet bargain or revel in the variety offered by all American department stores, you can expect shopping satisfaction.

          • Magnificent Mile has a range of big-name luxury brands. Indulge in some serious retail therapy, or maybe just some more-affordable window shopping.
          • Iconic US department stores are a Chicago specialty - Nordstrom, TJ Maxx and Macy's are dying to meet you.
          • Top up your energy levels with a snack at Garrett Popcorn. Who knew that popcorn could be this exciting!
          • Wicker Park and Bucktown offer some grittier shopping options, if you like fossicking for unique purchases in a less-touristy environment.
          • Fashion Outlets of Chicago in Rosemont is all about bargains, twofers and out-of-season specials. It's a 30 minute taxi ride from the city.
          • You'll have new clothes to show off, so dine fine tonight. Book into Elske, Entente, Alinea, Grace or Smyth (one word names are hot in Chicago at the moment).
            6Pancakes, blues and beer day1 day

            Today's really about music and beer, but you'll need something to fill in the morning. We suggest pancakes, they're a Chicago specialty. Batter up!

            • Hike to the nearest famous pancake house. Suggestions include Cindy's, Wildberry Pancakes & Café, Eggy's Diner, The Original Pancake House or Sweet Maple Café in Little Italy.
            • Tour a craft brewery, such as Revolution Brewing, Begyle Brewing, Goose Island Beer Company, Lake Effect Brewing Company or Empirical Brewery.
            • Find a gastropub for lunch. Maybe today's the day for a smoked beef brisket sandwich? In Chicago, sandwiches are an edible art form.
            • Start your magical music tour. If you want to focus on blues, consider B.L.U.E.S, Kingston Mines and Buddy Guy's Legends. There are numerous venues, so ask your hotel to recommend a couple.
            • If jazz is more your style, check out the Green Mill Cocktail Lounge - Al Capone was once a part-owner. Other famous jazz clubs include Andy's, Constellation and Winter's.
              7Nature day1 day

              There's a natural side to Chicago, involving beautiful parks, lakefront trails, wildlife sanctuaries and beaches, so factor in some fresh air for a well-rounded itinerary.

              • Montrose Point Bird Sanctuary is laced with walking trails, and there's an amazing backdrop of city high-rises. There's also a beachside bar.
              • Palmisano Park a 27-acre picture of perfection that was a quarry, then a landfill, then a park. The theme is Midwestern prairie, so expect butterflies and wildflowers.
              • Chicago's Botanic Garden is bigger than big. It involves 26 gardens, nine islands, six miles of lakeshore and a massive waterfall.
              • South of the CBD is Promontory Point, a famous Chicago spot for lake views and picnics. The views back to the city are absolutely awesome.
              • Moreton Arboretum is a tree museum west of the city, complete with woodland trails and birds. You can rent a bike here and cycle the extensive trail system.

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