Chicago Itinerary 5 Days

What to Do in Chicago in 5 days

Spending 5 days in Chicago will help you thoroughly explore the beautiful city. With a number of attractions in store, no day in Chicago will be left dull. Below are the attractions that you must include in your 5-day Chicago itinerary to have a memorable vacation.

This Plan is Good for You if You Are:

  • Searching for best places to visit in 5 days in Chicago
  • Picnic ideas for family and kids for 5 days
  • Looking for accommodation, restaurants and what to do
  • Want to avoid mistakes generally made by tourists in Chicago
  • Want a sample Chicago itinerary for 5 days
  • Planning a long vacation with family and friends

Best Itineraries for 5 Day Trip to Chicago

Recent Itineraries: Chicago Trips for 5 Days

Make your travel planning easier by using these perfect 5 days in Chicago itineraries from our users and travel experts. Look out for wisely chosen places you would like to explore during 5 days in Chicago.

5 Days in Chicago Trip Itinerary

Nestled on Lake Michigan in the state of Illinois, Chicago is probably one of the most popular cities in the USA. 5 days in Chicago are enough to get a sense of the essence of this lovely city. Here is what you need to start with when planning a Chicago 5 day itinerary.

How to Spend 5 Days in Chicago?

Local sights to see

Chicago lies between being a concrete getaway and a nature escapade. It has both types of attractions in plenty and your Chicago 5 day itinerary will feature a varied style of attractions. Millennium Art with space for art, theater and a big ice rink is the first attraction that should feature in your list. After which, you can add Willis Tower, Navy Pier and Cloud Gate in your itinerary as well. If you are put up in Downtown Chicago, then you have plenty of other attractions to check out such as Hull House, Rookery Building, Chicago Cultural Centre, Fine Arts Building, Field Museum of Natural History, the Art Institute of Chicago and Lincoln Park.

Local experiences to have

If you want to spend 5 days in Chicago not like a tourist, but like a local then following are a list of experiences you must have while in the city. First is standing in the long queue for a delectable pie at the Bang Bang Pie shop, then moving onto buying one of the many merchandise which is printed by the designs of local painters. These designs are printed on t-shirts, laptop cases, phone covers and can be found at Threadless HQ. Then you can head to Empty Bottle- a pub that is 20 years old. If you like to drink away your time, then even Broken Shaker is pretty awesome. The last must thing to do in Chicago is to buy something vintage from Humboldt House.

Food that you must eat

Start with having the Chocolate Pecan Pie at the Bang Bang Pie Shop, then head on to eat the most well-crafted pizza at ‘Craft Pizza’. The must-try dishes when in Chicago are Au Cheval’s Cheeseburger, Pizza Puff at Albanio’s Pizzeria, Chorizo Stuffed Medjool Dates at Avec, Smoked Salmon at Calumet Fisheries, Atomica at Cetimas Puebla and Seoul Sassy Fried Chicken at Crisp.

Day trips to take from Chicago

When you are taking a 5 day trip to Chicago, you can consider exploring the nearby areas as well. The most popular trips to take from Chicago are to Milwaukee, Kettle Moraine State Forest and Holland.

There is plenty to see and to do in Chicago, provided you plan your trip perfectly. Book well in advance to get the best deals and definitely figure out the best time to visit otherwise you will end up going at a very unfavourable time.

Tours and Activities to Include

Traveling like a local without any help from trip planners is good. But here are some organised tours and activities that you must try

Best Hotels in Chicago for 5 Day Trip

This is the list of frequently added hotels in past by our travelers to their Chicago itinerary 5 days. Check out the hotels that suit you and add them to your trip plan.

With Less Days in Hand

Look out for 2 days or 3 days long weekend holiday ideas.

What Next?

Are you now ready with your Chicago bucket list? Create an itinerary to Chicago using our Free Trip Planner and check all the attractions off your list.