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Chicago Highlights

4 Days
Prices From:
US$ 1,192

FIRST-CLASS | TAILOR MADE: Chicago is a huge, vibrant expanse packed with history, striking architecture, a fine array of public art, and a delightful Great Lakes shoreline. Music fans can look forward to discovering its renowned jazz and blues heritage while from deep-dish pizza to 22 Michelin-starred restaurants, the city’s culinary scene is one of the best in America.

This 4-day escape to Chicago shows you why the Windy City still inspires, from its towering architecture to world-class cultural offerings, to delicious local specialties. In Chicago, it’s not just the transit that’s elevated.

If you arrive early, consider a boat tour on the Chicago River for a close-up look at how the city’s famous bridges and skyscrapers create an urban layout that is uniquely Chicago. Spend a few hours exploring the Art Institute of Chicago or the Field Museum, home of ‘Sue’ the T-Rex skeleton, and the fearsome man-eating (now safely taxidermized) lions of Tsavo. Don’t rush to do everything. That’s what your Hop-On Hop-Off bus ticket is for on day two. Get an eyeful of Chicago from the top of the Willis Tower or the John Hancock Center, or come face to fin at the Shedd Aquarium. The following day, dive deeper into Chicago on a two-hour architecture and tasting tour. Snap your bendy-reflection photo at Cloud Gate, aka The Bean, and tour local eateries in The Loop that have been serving up Chicago favourites like deep-dish pizza for generations. You’ll also learn the particulars of how they’re done. At the end of your half-day tour, pick up any sights you’ve missed so far, chill out in Lincoln Park, or just enjoy wandering this charismatic city by the lake.


At Goway we are experts at designing personalized itineraries to suit your special interests, tastes and budget. Let us arrange your ultimate travel experience today.
4 Days
Prices From:
US$ 1,192

Itinerary View Trip Map

Day 1

Arrive Chicago

On arrival in Chicago, make your own way to your downtown hotel.

The balance of the day is at lesiure to relax or begin your exploration of the Windy City at your own pace.

Duration3 Nights

Kimpton Hotel Monaco Chicago

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    Kimpton Hotel Monaco Chicago

    This boutique hotel is located at the heart of Chicago, with a view of the Chicago River. It is a short walk to Magnificent Mile, Millennium Park and Navy Pier. Many restaurants, bars and shopping venues as well as links to the public transport network …

    This boutique hotel is located at the heart of Chicago, with a view of the Chicago River. It is a short walk to Magnificent Mile, Millennium Park and Navy Pier. Many restaurants, bars and shopping venues as well as links to the public transport network are to be found in the surrounding area. This 14-storey establishment was built in 1912. It comprises a total of 192 rooms with facilities including a selection of shops, a hairdresser's salon and Internet access. Dining options include a bar and a restaurant that offers regional specialities. Business guests may make use of the conference rooms, and those arriving by car may make use of the hotel car park.

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Day 2

Full Day Chicago Big Bus Hop-on Hop-off Sightseeing Tour

From your vantage point on the double-decker sightseeing bus, you'll enjoy panoramic views of Chicago's finest skyscrapers, including the 875 N Michigan, the Willis Tower, and the Wrigley Building.

Take in the city's impressive landmarks as your tour guide provides entertaining commentary and insight into Chicago's history. Enjoy exploring this dynamic city with the freedom to hop on and hop off as many times as you wish to visit attractions such as the Shedd Aquarium and the Field Museum.

You'll travel down the famous Magnificent Mile, considered one of the great avenues of the world, and continue across the Michigan Avenue Bridge over the Chicago River.

This hop-on, hop-off bus tour of Chicago makes it easy for you to explore the city's sights at your own pace. All stops are conveniently located to make navigating your way around the city easy, and you can take your time discovering Chicago.

Duration24 Hours
Day 3

Half Day Chicago Architecture and Food Walking Tour with Tastings

Experience the best of Chicago on a guided walking tour that explores the city's architecture and food culture.

Your 2-part walking tour begins by exploring the heart of Downtown Chicago. Join your guide as you discover the city's architectural highlights, both old and new. Admire views of the Chicago River, see Chicago's City Hall, the Wrigley Building, the Water Tower, Cloud Gate, and much more.

Then, hit the Central Loop, where locals go to grab their favorite foods. Sample some of Chicago's famous fare and learn about the history behind street food staples in the Windy City.

Let your local guide show you the how-tos (and how-not-to) of legendary dishes, from deep dish pizza to sandwiches, to a loaded hot dog. Listen as they entertain you with fascinating stories of the everyday immigrant chefs and vendors responsible for Chicago's eclectic food scene.

By the end of the tour, you'll have a deep appreciation for both the evolution of this city and the role food has played in the lives of its residents.

Duration5 Hours
Day 4

Depart Chicago

Today make your own way back to the Airport, of course if you have more time stay in the area!

Other Information




  • 3 nights first-class accommodation in Chicago
  • Shared Chicago Big Bus Hop-on Hop-off Sightseeing Tour
  • Small Group Chicago Architecture and Food Walking Tour with Tastings


  • Travel insurance
  • International and domestic airfare & airfare taxes
  • Entrance fees not explicitly listed as included
  • Meals and beverages not mentioned
  • Gratuities
  • Items of a personal nature
  • Visa fees if applicable


Prices are "from" per person based on twin/double shared accommodation and for travel in low season. Seasonal surcharges and blackout dates may apply. Limited seat/spaces and all pricing is subject to change and availability. Rates for single or triple travellers are available on request - please inquire.

31 Aug 2023
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