Chicago city break

Stopover packages
Duration (in days): 4

From: Chicago

To: Chicago



Exc. International flights (per person, based on 2 sharing) 
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Explore the windy city on this short Chicago city break stopover. Chicago is a wonderful place to spend a few days whether you wander along the canals, watch a baseball game at Wrigley Field or simply stuff yourself with the signature deep-dish pizza. Explore two of America’s best museums; the Art Institute of Chicago and the Field Museum - before strolling along the lake front with views over Lake Michigan. Why not finish your time here with a show at Second City, a comedy club that has produced some of America’s finest comics – or take a trip up the Willis Tower Skydeck, for views over the twinkling lakeside city below.

This itinerary can be tailored to suit your requirements please contact one of our consultants to start planning your dream trip.


  • Wander amongst the exhibitions at the Art Institute of Chicago
  • Catch a baseball game at Wrigley Field
  • Enjoy views over the city from the Skydeck of Willis Tower
  • Try a slice of famous Chicago deep dish pizza

Day 1: Arrive Chicago

On arrival in Chicago you’ll make your own way to the airport and check into your hotel for three nights.

Days 2 & 3: Chicago

Two days is enough time to enjoy the highlights of Chicago. Start with a trip to the Cloud Gate, more popularly known as “The Bean” where you can snap a photo in its distorted reflection, before heading to Intelligentsia Coffee for a latte. We’ve included the Chicago City Pass so you can use it to explore two of America’s best museums. The Art Institute of Chicago holds paintings by Picasso and O’Keefe, as well as the famous American gothic portrait by Grant Wood, while at the Field Museum you can visit Sue, the most complete T-Rex skeleton ever found.

Enjoy a slice of Chicago deep dish pizza at Giordano’s before a night of comedy at Second City, where many famous comedians made their debuts. Don’t leave before heading to the top of the Willis Tower SkyDeck, where you can stand in a glass box high above the city and admire endless views of the city and Lake Michigan below.

Day 4: Depart Chicago

Your time in Chicago has come to an end today so make your own way to the airport in time for your onward flight.



Chicago has four distinct seasons – hot summers, mild autumns, snowy winters and wet springs. It’s often cloudy and a bit windy thanks to the city’s location on the shores of Lake Michigan

This itinerary is purely a suggestion, and can be tailor-made to your requirements, so please contact us with your dates and requests and we’ll put together a bespoke quotation for you.

What's included: 

  • Accommodation for 3 nights
  • City Pass

Not included: 

  • Transfers
  • Meals
  • Tips and personal expenses

3 nights in 3* standard accommodation.

Hotels in this category include:

  • Best Western River North Hotel


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