Chicago Itinerary 7 Days

This is a glimpse of what to see in 7 days in Chicago from Chicago itinerary 7 days created by our travel experts. These are the attractions one must visit while planning a 7 days trip to Chicago.

7 Days in Chicago - Perfect 1 Week Guide

Chicago is a city that is laid back one minute, and the next second, you will find it bursting with energy. Often compared to some of the top cities in the country, it is on the top, but once you set your foot in its boundaries, you will know that it offers so much more than the rest! Whether it be the Willis Tower, Cloud Gate, the Shedd Aquarium, or the Lincoln Park Zoo, the city has everything from parks and garden, to markets and shopping, from museums and art centers to piers and planetariums! Some of the top attractions in the city include Museum of Science and Industry, Wrigley Field, Burnham Park and more! Take a look at what all you can include in your Chicago Itinerary 7 Days before you plan your trip!

Are 7 days enough for vacation in Chicago?

Seven days in Chicago gives you a chance to visit the popular, and explore the unexplored. If you are wondering about what to see and what to do, TripHobo has the perfect plans that'll help you make the most of your week long vacation in Chicago.

Packing Lists For Chicago For 1 Week

One week in Chicago, Carry all of your essentials and a few more things that will make your Chicago tour easy and exciting. Camera, journal, comfortable clothing and quick snacks are a must. You can also carry apparel for special events like concerts, fine dining restaurants and shows in case you plan on attending one. An extra pair of shoes, a little cash and some warm clothes in case the weather in Chicago decides to play a trick on you! Check out the best time to visit Chicago before you plan your vacation. Don't pack less, just pack cleverly!

How much spending money for 7 days in Chicago?

A typical budget for comfortable one week trip to Chicago is USD 1778 per person including airfare, car rental and daily expenses. If you like to shop, adjust that number upward as needed.

What to see in Chicago in 7 days?

Top sites and experiences

Skydeck: Head here for a dinner date and indulge in the famous deep-dish pizza! There are many activities that take place here during the day that you can be a part of.
The Field Museum: One of the best natural history museums, it is in its vicinity that you will find some more interesting museums that you must visit. Dedicate a day to the museums to get the best out of them.

Robie House: Showcasing the 20-century Prairie-style architecture, it boasts of being one of the very few Frank Lloyd Wright buildings that one can tour.

Art Institute of Chicago: One of the best museums in the world, it houses the artworks of famous artists including Vincent van Gogh, Henri de Toulouse-Lautrec, and Claude Monet.

Festivals: Summer in Chicago brings all the people out on the streets. Music, food, shopping, dance and tours at their best during this season, you will find many streets turning into parties and fairs!

Beer touring: Revolution Brewing Tap Room, Half Acre Brewery Balmoral, Dovetail Brewery, and Forbidden Root are some of the top breweries in Chicago. Set an afternoon aside to go brewery hopping!

Unusual places to go

7 Days in Chicago gives you plenty of time to see all the important sites, as well as indulge in the whimsical quirky mood of the city. Here are some of the unique places to visit while in the city.

Oz Park: Based on the famous and most loved story of the Wizard of Oz, the Oz Park is a fun place to visit, especially with children.

Wicker Park Secret Agent Supply Co.: One for the Sherlocks hidden in all of us, this eccentric store is a delight! Head to any of the other themed stores, and you will have the best time!

Free things to do

Chicago is a city which will, without you noticing, manage to make your wallet a little light. And although all that you experience here is totally worth it, if you do find yourself looking for budget or free things to do, you do have some great activities which will help you save money and treat you to a different personality of this vibrant city. From touring some centers and museums, to the famous Chicago Greeter program that allows you to meet tourists and set out on a tour with a local, you have great options. Take the Chicago Lakefront Trail and be overwhelmed by how the quiet morning trail that overlooks the waters, turns into a buzzing port at night!

When it comes to free places to visit in the city, Millenium Park should actually be at top of the list. The identity of this town lies here, and a visit here is a must! While talking about identity, a visit to the Lurie Garden should also be on your list. Displaying the different hues of the seasons, this garden offers beautiful views of the city. Plan one evening at the Navy Pier to watch the free fireworks!


1 week in Chicago brings with it the exciting opportunity to explore the shopping areas. Whether it be the boutiques that define the neighborhoods, or The Magnificent Mile that is known for its fancy brands, shopping in Chicago is an experience that one must not miss. From

The Magnificent Mile: Undoubtedly one of the best avenues to go shopping, the ‘Mag Mile’ stretches over 8 blocks where more than 400 retailers proudly showcase their chic labels.

The Shops at North Bridge: 50 specialty shops, 20 fine restaurants, stretching over 6 blocks makes The Shops at North Bridge the second most preferred shopping avenue.

Randolph Street Market: The perfect place to find trinkets, vintage items and more, Randolph Street Market is a fun place to explore

Neighbourhood Boutiques: Stroll along the various parts of the city, and chic boutiques shine along, changing the aura of the neighborhood. Some of these areas are Oak Street in the Gold Coast, Andersonville and even Lincoln Park.

Let your 7D6N long itinerary of Chicago include everything from museums to shopping avenues and flea markets, food to beer, and the waterfront to the buildings that touch the clouds!

Travel tips for visiting Chicago with family and friends

Travelling in groups is fun, but chances of missing out on something is also increased. So, if you are travelling to Chicago with your family and friends, keep some of these tips in mind.

  • Be on time to avoid missing out on the tourist attractions of Chicago.
  • Carry all the essentials like water and snacks, and any medicines that you may require.
  • Group bookings means budget bookings, avail of such deals and save a couple of bucks.
  • Spend time with one another, indulge in some together-time and have a blast!

Getting around Chicago in one week

Chicago is well equipped with a seamless transport system. While you will find buses and other means of transport connecting all the various parts of the city, commuting on foot is the best way to understand the city and its essence. Car and bike rentals are also available.

Best restaurants in Chicago

Try restaurant for some traditional delicious recipes while you are in Chicago. The best way to indulge in the authentic delicacies is by consulting the locals, so, dig in!

Chicago holiday apartments and vacation rentals

Seven days is a considerable amount of time, and what better way to explore Chicago than to try out a couple of accommodations! Pick different areas, and different types of accommodation services to understand the vibe of the city better. You have a number of options like bed and breakfasts, hotels, resorts and hostels in Chicago.

Other 7 Days Itineraries to explore in the United States:

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