4-Day Adventure & Shopping Itinerary for Friends in Chicago
Chicago, Illinois
4 days
About Chicago, Illinois
Experience the vibrant city of Chicago, Illinois, a bustling metropolis known for its stunning architecture, rich history, and diverse culture. Marvel at the city's skyline from the Skydeck of Willis Tower, or stroll along the Magnificent Mile for a shopping spree. Explore the world-class museums like the Art Institute of Chicago and the Field Museum. Enjoy the city's culinary scene, from deep-dish pizza to fine dining. Visit Navy Pier for entertainment and Lake Michigan for a scenic view. Sports enthusiasts can catch a game at Wrigley Field, while music lovers can enjoy a show at the Chicago Theatre. Don't forget to visit Millennium Park and see the iconic Cloud Gate, also known as "The Bean". Chicago offers a unique blend of urban exploration and Midwestern hospitality that leaves every visitor captivated.
4-Day Itinerary
Day 2
Active City Tour
Morning
Begin your day with a bike tour of the city. This is a fun and active way to see the sights and get a feel for the city.
Lunch
For lunch, try a local deli. These places offer a variety of sandwiches and salads and are a great way to refuel during your busy day.
Afternoon
Spend your afternoon exploring a local park. This park is known for its beautiful gardens and scenic views. It's a great place to relax and enjoy the outdoors.
Dinner
For dinner, try a local seafood restaurant. These places offer fresh, local seafood and are a great way to experience the local cuisine.
Evening
End your day with a visit to a local comedy club. Chicago is known for its comedy scene and this is a great way to experience it firsthand.
Day 3
Historical and Culinary Experience
Morning
Start your day with a visit to a local Flea Market. This is a great place to find unique items and souvenirs.
Lunch
For lunch, try a local pizza place. Chicago is known for its deep-dish pizza and this is a must-try during your visit.
Afternoon
Spend your afternoon exploring a local museum. This museum is known for its unique exhibits and is a great way to learn about the local culture and history.
Dinner
For dinner, try a local steakhouse. These places offer high-quality steaks and are a great way to experience the local cuisine.
Evening
End your day with a visit to a local craft brewery. Chicago is known for its craft beer scene and this is a great way to experience it firsthand.
Day 4
Nature and Shopping Adventure
Morning
Begin your day with a hike in a local Nature Reserve. This is a great way to enjoy the outdoors and see some of the local wildlife.
Lunch
For lunch, try a local vegetarian restaurant. These places offer a variety of healthy and delicious options.
Afternoon
Spend your afternoon exploring a local shopping district. This area is known for its unique boutiques and shops.
Dinner
For dinner, try a local ethnic restaurant. These places offer a variety of cuisines and are a great way to experience the diversity of the city.
Evening
End your trip with a visit to a local Rooftop Bar. These places offer great views of the city and are a great way to say goodbye to Chicago.
Attractions in Itinerary (4)
1Art District
Chicago's Art District, also known as the Pilsen East, is a creative hub known for its galleries, studios and vibrant murals. It's a must-visit for art lovers.
2Flea Market
Chicago's flea markets are a treasure trove of vintage goods, antiques, and unique finds. It's a fun shopping experience for bargain hunters and collectors alike.
3Nature Reserve
Chicago's nature reserves offer a peaceful retreat from the city, with walking trails, wildlife, and beautiful scenery. It's a great place for outdoor activities and relaxation.
4Rooftop Bar
Chicago's rooftop bars offer stunning views of the city skyline, along with a selection of drinks and food. It's a popular spot for a night out in the city.
Local Food and Drinks (12)
Deep-Dish Pizza
A Chicago classic, deep-dish pizza is a must-try. It's characterized by its thick, buttery crust, chunky tomato sauce, and generous layers of cheese. It's a staple in Chicago's culinary scene.
Italian Beef Sandwich
This sandwich is a Chicago original, featuring thinly sliced roast beef soaked in juices and served on an Italian-style roll. It can be ordered 'wet' (extra gravy) or 'dry'.
Chicago-Style Hot Dog
A Chicago-style hot dog is a steamed or boiled all-beef frankfurter on a poppy seed bun, topped with mustard, fresh tomatoes, onions, sport peppers, bright green relish, dill pickles, and a dash of celery salt.
Garrett Popcorn
A beloved snack in Chicago, Garrett Popcorn is known for its 'Garrett Mix', a blend of sweet caramel crisp and savory cheese popcorn.
Jibarito
A sandwich that originated in Chicago's Puerto Rican community, the Jibarito is made with flattened, fried green plantains instead of bread, and filled with meat, cheese, lettuce, and tomato.
Pierogi
A popular dish in Chicago's Polish community, Pierogi are dumplings filled with a variety of ingredients, such as potato, cheese, or sauerkraut.
Gyros
A popular fast food in Chicago, Gyros are Greek sandwiches made with slices of rotisserie-cooked lamb, beef, or chicken, served on pita bread with tzatziki sauce.
Shrimp DeJonghe
A Chicago original, Shrimp DeJonghe is a casserole dish that features whole peeled shrimp blanketed in soft, garlicky, sherry-laced bread crumbs.
Paczki
A traditional Polish pastry, Paczki are deep-fried pieces of dough filled with sweet filling and covered with powdered sugar or icing. They are especially popular in Chicago on Fat Tuesday.
Malört
A bitter liquor, Malört is a Chicago original. It's known for its strong, unique flavor that's often described as tasting like grapefruit and gasoline.
Chicago-Style Popcorn
Another popular snack in Chicago, this popcorn is a mix of sweet caramel and savory cheese flavors, offering a unique and addictive taste experience.
Craft Beer
Chicago has a thriving craft beer scene, with many local breweries producing a wide variety of unique and flavorful beers.
Best time to visit
The best time to visit Chicago, Illinois is from April through October. During these months, the city offers pleasant weather, making it perfect for sightseeing, outdoor activities, and festivals. However, if you're interested in less crowded attractions and cheaper accommodations, the shoulder seasons, which are April to June and September to October, would be ideal. The summer months, July and August, are the peak tourist season with numerous events and festivals taking place.
National holidays
Here you can find the national calendar of all public holidays for the year. These dates are subject to change as official changes are announced, so check back regularly for updates.
| Date | Day | Holiday Name |
|---|---|---|
January 1 | Mon | New Year's Day |
January 15 | Mon | Martin Luther King Jr. Day |
February 19 | Mon | Presidents' Day |
May 27 | Mon | Memorial Day |
June 19 | Wed | Juneteenth |
July 4 | Thu | Independence Day |
September 2 | Mon | Labor Day |
October 14 | Mon | Columbus Day |
November 11 | Mon | Veterans Day |
November 28 | Thu | Thanksgiving Day |
December 25 | Wed | Christmas Day |
How to get around
CTA (Chicago Transit Authority)
The CTA operates the nation's second largest public transportation system. It includes a network of buses and trains that cover the city and 35 surrounding suburbs. The 'L' train system has eight rapid transit routes and consists of 145 stations.
Metra
Metra is a commuter rail system that serves the city of Chicago and its surrounding suburbs. It operates 11 lines and 242 stations, making it an efficient way to travel to and from the city's outskirts.
Pace Bus
Pace provides bus services throughout the Chicago suburbs and complements the service provided by CTA and Metra. It operates 241 routes, including express, local, and feeder bus services.
Divvy Bikes
Divvy is Chicago's bike sharing system with thousands of bikes available at hundreds of stations across the city. It's a fun, affordable and convenient way to get around, especially when the weather is nice.
Ridesharing (Uber, Lyft)
Ridesharing services like Uber and Lyft are widely available in Chicago. These services provide convenient, on-demand transportation throughout the city and suburbs. They can be accessed through smartphone apps.
Taxis
Taxis are plentiful in Chicago, especially in the downtown area. They can be hailed on the street, at taxi stands, or booked via phone or app.
Water Taxi
Chicago's Water Taxi operates on the Chicago River and provides a unique mode of transportation. It's a great way to see the city's architecture and avoid traffic during rush hour.
Driving and Parking
While driving can be convenient, it can also be challenging due to traffic and expensive due to parking costs. There are numerous parking garages and metered parking spots throughout the city, but be aware of restrictions.
Walking
Chicago is a very walkable city, especially in the downtown area where attractions are close together. The city's grid system makes it easy to navigate.
Biking
Chicago is a bike-friendly city with many bike lanes and paths, including the 18.5-mile Lakefront Trail. You can bring your own bike or rent one from a bike-sharing service like Divvy.
Airport Shuttles
Several companies offer shuttle services to and from Chicago's two major airports: O'Hare and Midway. These shuttles can be a cost-effective option for travelers.
Important information
Currency$ USD
Time zoneUTC-5
Driving sideRight
Emergency phone911
Drinking waterYes
Power sockets
Voltage120 V
Things to know about Chicago, Illinois as a first time visitor
1
Chicago is located in the Central Time Zone.
2
The city is known for its unpredictable weather. Always check the forecast before your trip.
3
Chicago is a very walkable city, but it also has a comprehensive public transportation system, including buses and the 'L' train.
4
Tipping is customary in Chicago. It's standard to tip 15-20% at restaurants and for services.
5
The city is known for its food. Don't miss out on trying a Chicago-style hot dog or deep-dish pizza.
6
Sales tax in Chicago is 10.25%, one of the highest in the U.S.
7
Chicago is a city of neighborhoods, each with its own unique character and charm.
8
The city is located on Lake Michigan, which can make it feel colder due to the 'lake effect'.
9
Chicago is a sports-loving city, home to the Cubs, White Sox, Bulls, Bears, and Blackhawks.
10
The city is very bike-friendly, with numerous bike lanes and bike-sharing programs.
11
Chicago is known for its music scene, particularly blues and jazz.
12
The city has strict smoking laws. Smoking is banned in all indoor public places and within 15 feet of any entrance.
13
Chicago's O'Hare International Airport is one of the busiest airports in the world.
14
The city is known for its architecture. Consider taking an architectural tour.
15
Chicago has a high sales tax on bottled water, so consider bringing a reusable water bottle.
16
The city can get very cold in the winter, with temperatures often dropping below freezing (32°F/0°C).
17
Chicago's summers can be hot and humid, with temperatures often reaching into the 80s and 90s Fahrenheit (27-32°C).
18
The city is known for its vibrant arts scene, including theater, visual arts, and music.
19
Chicago is a diverse city with a rich history of immigration, which is reflected in its food, neighborhoods, and festivals.
20
The city has a reputation for being windy, hence its nickname 'The Windy City', but this is more due to its political history than its actual weather.
Packing List
Clothing
Underwear
Socks
T-shirts
Pants/Jeans
Sweater or Jacket
Pajamas
Comfortable walking shoes
Dress shoes
Swimwear (if planning to swim)
Accessories (belts, jewelry, etc.)
Weather appropriate outerwear (raincoat, umbrella, sunglasses, hat, gloves, scarf)
Toiletries
Toothbrush and toothpaste
Shampoo and conditioner
Body wash or soap
Deodorant
Razor and shaving cream
Makeup and makeup remover
Hairbrush or comb
Hair styling products
Sunscreen
Prescription medications
First aid kit
Travel documents and essentials
Valid ID or Driver's License
Passport (if traveling from outside the U.S.)
Airline tickets or e-ticket confirmation
Hotel and/or car rental reservations or confirmations
Credit and/or debit cards
Cash and/or traveler's checks
Emergency contact information
Travel insurance documents
Guidebooks, maps, and directions
Electronics and gadgets
Mobile phone and charger
Laptop and charger (if needed)
Headphones or earbuds
Camera and charger
Memory cards or film for camera
Portable power bank
Travel adapter (if traveling from outside the U.S.)
Miscellaneous items
Snacks for travel
Reusable water bottle
Books or e-reader for entertainment
Travel pillow and blanket
Luggage tags
Laundry bag
Ziplock bags for toiletries
Travel-sized detergent (if planning to do laundry)
Weather Conditions
Chicago, often referred to as the "Windy City", experiences a wide range of weather conditions throughout the year, so it's important to plan your visit accordingly. Spring (March to May) in Chicago can be unpredictable, with temperatures ranging from 40°F to 70°F (4°C to 21°C). It's a good idea to pack layers and a waterproof jacket as rain showers are common during this season. Summer (June to August) is typically warm and humid, with temperatures often reaching up to 85°F (29°C). However, it can occasionally get hotter, so don't forget your sunscreen, hats, and light clothing. Also, be aware that Chicago can experience severe thunderstorms during the summer months. Fall (September to November) is a beautiful time to visit Chicago as the leaves change color. Temperatures can vary greatly, from 70°F in September (21°C) to 40°F in November (4°C). A light jacket and umbrella are recommended as rain can be frequent. Winter (December to February) in Chicago can be quite harsh, with temperatures often dropping below freezing, sometimes as low as 20°F (-6°C). Snowfall is common and can be heavy, so pack warm clothing, including a winter coat, gloves, and a hat. Regardless of when you visit, keep in mind that Chicago's weather can change quickly. It's always a good idea to check the forecast before your trip and pack accordingly. Also, remember that the wind can make it feel colder than the actual temperature, especially near the lakefront. Finally, don't let the weather deter you from enjoying all that Chicago has to offer. There are plenty of indoor attractions like museums, art galleries, and restaurants to enjoy if the weather isn't cooperating.
| Month | Hi / Lo (°C) | Weather Overview |
|---|---|---|
January | 1° / -9° | January is the coldest month in Chicago, with snow and freezing temperatures, so pack warm clothes. |
February | 3° / -7° | February is still quite cold with a chance of snow, but temperatures start to rise slightly. |
March | 9° / -3° | March sees the beginning of spring, with temperatures rising, but still expect some chilly days. |
April | 16° / 3° | April is a transitional month with temperatures ranging from chilly to mild, and occasional rain showers. |
May | 21° / 8° | May is the start of the warm season, with pleasant temperatures and more sunny days. |
June | 26° / 13° | June is a great month to visit Chicago, with warm temperatures and plenty of sunshine. |
July | 29° / 16° | July is the hottest month in Chicago, with high humidity and plenty of sunshine. |
August | 28° / 15° | August is still quite hot, but temperatures start to cool down towards the end of the month. |
September | 23° / 11° | September is a pleasant month with mild temperatures, perfect for outdoor activities. |
October | 17° / 5° | October sees the arrival of fall, with cooler temperatures and beautiful fall foliage. |
November | 10° / -1° | November is a transitional month with temperatures dropping and the first signs of winter. |
December | 4° / -6° | December is a cold month with a high chance of snow, so pack warm clothes if you plan to visit. |
Did you know?
Places near by Chicago, Illinois
Starved Rock State Park
A beautiful outdoor park with hiking trails and waterfalls.
Indiana Dunes National Park
A national park on the shore of Lake Michigan offering a wide range of activities.
Six Flags Great America
A large amusement park with a variety of rides and attractions.
Milwaukee Art Museum
An art museum with a collection of over 31,000 works.
University of Notre Dame
A private Catholic research university known for its historic campus, collegiate gothic architecture, and strong athletic tradition.
Kettle Moraine State Forest
A state forest known for its glacial landforms, such as kettles, moraines, and kames.
Madison
The capital of Wisconsin, known for its vibrant cultural scene and beautiful lakes.
Springfield
The capital of Illinois, known for its association with Abraham Lincoln.
St. Louis
A major city in Missouri along the Mississippi River, known for its iconic Gateway Arch.
