Perfect 2 days in Chicago Itinerary and travel guide

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Looking for an epic 2 days in Chicago Itinerary? We got you covered. There are tons of ways to discover the iconic sights of Chicago, but giving just a couple of days to get immersed in the skyline of such an impressive city is just asking for too much from the hopeless visitor. 

America’s third-largest city is known to outgrow her prophecies much faster than she can even make them, still with just forty eight hours in hand, here are some insider tips by which you can squeeze in most of the popular attractions by way of a whirlwind two day Chicago itinerary.

2 days in Chicago Itinerary: How to plan a trip to Chicago

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Traveling to any new city can be daunting for any first time visitor, especially if it is the third largest in the United States. These tips will show you how to blend with the locals and boost your travel experience to Chicago.

Getting to Chicago

Chicago is served by the Chicago O’Hare International Airport aka ORD. You can fly there internationally from Canada, Europe, and other parts of the USA and the world. 

It is easy to access downtown Chicago from the airport by public transportation. The Blue Line ‘L’ train will take you from O’Hare to downtown in about 45 minutes, and will cost about $5 USD. You can get to the Blue Line from Terminals 1, 2, and 3, and follow signs to “Trains to the City.”

Shuttle buses will take you from the airport Shuttle to the city. The pick up location is at the Bus Shuttle Center. 

You can also take a taxi downtown, and it will cost you about $30 to $40 USD. Book a private transfer for 3 here

Where to stay in Chicago

There is no dearth of quality accommodation in Chicago, but choosing the one which is ideally suited for your short trip is the essential part. 

The centrally located River North area makes the perfect base to explore the city. The neighborhood is 25 km or 15.5 miles away from the airport and 1 km away from the John Hancock Tower and Millennium Park. 

Moreover, another important landmark, the Magnificent Mile is just 2 km or 1.2 miles away.

If you book your accommodation within a half mile area of the intersection of North Michigan Avenue and the river, you will be a short walk away or a train or bus ride to almost any attraction a visitor may want. 

Remember to ask for a room on the top most floors of your hotel for wonderful views of Chicago.

• Westin Chicago River North: This is one of the luxurious properties in Chicago, offering beautiful suites by the riverside. You are at the heart of the city, and sightseeing and galleries are just a short walk away. Check prices and availability here
• Home2 Suites by Hilton Chicago River North: This is a mid range hotel in the same neighborhood. The rooms are spacious and clean, and they also offer complimentary breakfast in the morning. Book your stay here

Chicago has some unique staying options like the Palmer House or the Chicago Athletic Association. For boutique hotels try the Robey or the Freehand.

Click to search more hotels in Chicago for your stay

Day 1 of 2 days in Chicago Itinerary: River North, Millennium Park, Cloud Gate Sculpture, Maggie Daley Park, Art Institute of Chicago, Navy Pier, Architecture River Cruise, Chicago Children’s Museum, Magnificent Mile, Drunk Shakespeare Society in the evening, Riverwalk at night

Spend the morning in Millennium Park, check out the prime attractions, and go on an architectural cruise

River North is a prime location for shopping, activities, and restaurants and should be the starting point of the first day Chicago itinerary. Begin the morning with a traditional American breakfast at Meli Cafe on the North Side for a five star offering on a one star budget.

Now that you are charged up, stroll down to Millennium Park, the largest public area in Chicago. The park features an outdoor venue used for concerts, the Jay Pritzker Pavilion, Lurie Gardens, and the shopping areas adjacent to it. The park is also the venue of the Tree Lighting Ceremony which takes place during Christmas. 

Another highlight here is the highly reflective Cloud Gate Sculpture, also known as “The Bean” which captures the skyline of some of Chicago’s iconic buildings like the Aon Center among others.

Connected to Millennium Park by the BP bridge is Maggie Daley park, another spectacular open space in the heart of the city. The two main features here are the Play Garden and Skating Ribbon which has made this place a phenomenal success as they are designed for children of all ages. 

Chicago’s first and only Climbing Park is also located here. With the unparalleled skyline as your backdrop, you will find this park an organic natural experience.

If you prefer to explore Chicago with a local, book this 2.50 hour History, Culture & Architecture Tour

Next, explore the arty side of the city by visiting the second largest art museum in America. Five minutes of leisurely walking will bring you in front of the lion statue outside the Art Institute of Chicago. 

Ranked at one time as the best of its kind in the world, the building holds a great collection of paintings by renowned artists, with some masterpieces spanning over thousands of years.

It is now mid-morning and loads of attractions are waiting to be explored. Twenty minutes walk from the Art Museum will bring you to the Navy Pier from where you can take a 75 minutes cruise by water taxi down the Chicago River with English speaking commentary who do a great job to make the trip as enjoyable as possible for visitors.

The seating is open and a full service bar is in full swing as you sit back and pass by over 50 important buildings on either side of the river. Some of the top institutions you will see are:

• The John Hancock Center

• The Aon Tower

• The IMB buildings

• The Wrigley Building

• Willis Tower

Book: 75 minute architecture cruise

Or book an evening cruise (1.50 hours)

For the afternoon, explore more of Navy Pier and try Deep Dish Pizza!

The hectic up and down walks would have left you famished by now. After alighting from the cruise grab a delicious burger at the Billy Goat Tavern next to the pier. They are a bit overpriced, but the ambiance and the fresh ingredients they use are worth every penny spent.

Navy Pier is itself very crowded and touristy, with a carnival-like atmosphere. Moreover, if you walk all the way down the 3300 feet you will be rewarded with splendid views of downtown. The pier is also home to the famous Chicago Children’s Museum and should not be overlooked on any Chicago trip.

It is now time to get ready to walk the Magnificent Mile, one of the must-see upscale streets, comparable with the Fifth Avenue of New York City, which is located at the northern end of Michigan Avenue.

This expensive commercial center features some of the tallest buildings of the city like the Wrigley Building and the survivor of the devastating Chicago fire of 1871, the Historic Water Tower.

How can anyone visit Chicago and not take a bite of the city’s most iconic dish, the Deep Dish Pizza? 

The Pizzeria Uno in the River North neighborhood has been making pizzas since 1940 and the spectacular ambiance made for a good place to rest tired legs and grab an opportunity to dig into this well-known rendition. The deep-dish comes with offerings like spinach, mushrooms, and a triple topping of mozzarella cheese.

You might like: 2.5 hour Chicago food tasting tour

Finish the day with a Broadway show, and a lovely stroll at the Riverwalk

Chicago has a very active theatre scene supporting some Broadway shows which are held in various venues in the city. Irrespective of whether you are a theatre buff or not, a visit to a Broadway show is a must. 

Off late the Drunken Shakespeare Society has gained in popularity because of their unique audience involvement in their programs. An actor downs five shots of whiskey and then tries to perform a Shakespeare play on stage. If you intend to visit, book in advance as tickets sell fast and you may not have a day to spare.

In order to make the primary river of Chicago more sustainable and meaningful to the public, the riverside project was completed in 2016. The Riverwalk has many walking paths and offers a wonderful opportunity to sit at a cafe and enjoy a drink in this urban oasis. 

It makes for a wonderful late-night walk at the end of a taxing first day to enjoy the reflections of the well-lit city in the water. The Riverwalk is open 24 hours and you can walk there any time of the night from State Street to Lake Street.

Day 2 of 2 day Chicago itinerary: Breakfast, Willis Tower, John Hancock Building, Field Museum, Lake Shore Drive, Dinner Cruise

Check off the Willis Tower, and soak in city views from 360 Chicago

Stan’s Donuts on the Magnificent Mile is a nice place to begin the day with coffee and donuts. After your first day, you will now be more or less familiar with downtown Chicago.

The city being the birthplace of the modern skyscraper, a visit to either of the two noteworthy sky deck options is a must. The Willis Tower (formerly Sears) is where most visitors tend to land up as not only it is famous but also the tallest on the 103 floors of the 110 storey building.

The entrance is on the ‘L’ line but you will have to reach here early if you want to avoid the long lines as on a busy day the waiting time could be 2 and ½ hours. 

Another alternative is the 360 Chicago skydeck in the John Hancock Building which offers a similar experience, albeit with a much shorter wait of five minutes. The John Hancock Center on Michigan Avenue is accessible via the red metro line. 

Book entry tickets to the Observation deck – 360 Chicago

Explore the Field Museum 

From mummies of ancient Egypt to Sue, the largest and most T-Rex dinosaur fossil in the world, the Field Museum must be ticked off on your short stay in Chicago.

Other compelling exhibits show the evolution of mankind over four billion years. 

The place is crowded but a must for a couple of hours time minimum. Book entry tickets to Field Museum in advance

Go on the Lake Shore Drive in the afternoon 

Lake Shore Drive is a 15+ miles stretch of the multi-level urban passageway on US 41 best experienced by driving from  Hollywood Ave in the south to Marquette Drive in the north. 

It is a wonderful way to spend the afternoon admiring the parks, cultural icons, and historical buildings that face the beautiful Lake Michigan. There are many good stopping points and picnic spots on the famous roadway. Some of the best views of the city’s skyline can be had from Promontory Point.

Go on a dinner cruise to sign off your Chicago 2 day itinerary

Pamper yourself on your last evening with a few hours of fun and an unbeatable culinary experience with a night out on the water in Chicago. This three hour cruise on Lake Michigan with a delicious plated dinner using the freshest of ingredients is a wonderful setting with a 360° view of all the landmarks and the skyline of the city. 

On-board entertainment includes a live DJ and a dance floor to add spice to the event. The tour departs at 730pm from the Navy Pier. Book your dinner cruise here

Other things to do in Chicago in 2 days

If you have more time or have different interests there are dozens of other options to check out on your two days in Chicago. 

If you are an art lover, the 1929 Lyric Opera House in the city center is a nice place to stroll by. 

Another option is to visit the Chicago Water Tower located Old Chicago Water Tower District (Michigan Ave)

You can try and catch a live jazz performance at the Green Mill Cocktail Lounge.

For sports, especially baseball fans, a visit to the Wrigley Field which was established in 1914 is the second oldest ballpark in America. You can tour this stadium either on game day or non-gameday days for a glimpse of what goes behind the scenes of this extremely popular American sport. If you have just two days, it may not be a must but if you love baseball it is definitely worth it.

Wherever you are staying in the city there is bound to be some event taking place in a park near you. There are as many as 77 different parks in the city that host over 2000 events in a year. 

If you consider Nights out in a Park you may either find some movie show going on, a themed party in progress, or a community bonfire for the whole family to partake in.

Daily tours in Chicago

A fun way to cut down both on the walking and experiencing Chicago at the same time is by booking a hop-on-hop-off bus tour.

Not only is it convenient but it covers all the major attractions with expert narrations in half a day leaving you time to explore other areas of the city. There are a number of operators, but BigBus Chicago has the best pick-up times.

If you wish to explore the city’s gangster past you can opt for a two hour Crime & Mob bus tour in a coach vehicle. This tour will cover the places in Chicago where the infamous thugs like Al Capone, John Dillinger, Hymie Wess, and the Untouchables used to operate from. 

River North’s Cathedral District is another neighborhood within a neighborhood and is known for some famous churches in the area. 

In an area of less than two square miles lies a mix of old and new churches such as the iconic St James Cathedral and the Holy Name Cathedral. The area boasts of many new high-rise structures and is one of the most sought-after districts for upscale living.

A well-versed guide will relate all the sordid tales about the past of these villains and their locations. These include the Holy Name Cathedral and the Biography Theatre which was the site of the bloody massacre on St Valentine’s Day with opportunities to take selfies and photo shoots.

For those travelers pressed for time, this is a quick and fast way to learn about the mob history of Chicago. Book this bus tour here

You can also book this as a walking tour – gangsters and ghost 

For visiting multiple museums, as well as 360 Chicago observation, consider purchasing the CityPass (valid for 9 days, it gives you 50% off on the top 5 attractions covered in this itinerary) 

Navigating Chicago

Chicago has many points of interest like Downtown Chicago and Michigan Avenue which can be easily explored by walking, but the city is so massive that relying on just your two feet is not likely to get you very far.

Thankfully, the city’s public transportation system, the second largest in the US, is well laid out and organized. While cash is acceptable on buses, you need to pay through the reloadable Ventra card for the EI which can be purchased at any station on the Loop, online via the Ventra app, or at certain retail locations such as Walgreens.

Chicago can also be conveniently toured by rideshare apps like Lyft and Uber. You can also choose to rent a bicycle for the full day from the Divvy bike share service because it is very much doable during the warmer months. While you can rent a car for two days in Chicago, parking comes at a premium hence it is not recommended.

Quick getaways and day trips from Chicago 

If you find the hustle and bustle of Chicago City overwhelming there are plenty of places at a short distance where you can take a much needed break.

Oglesby and Starved Rock State Park 

Between the Illinois and Vermillion rivers, lies the scenic town of Oglesby where the Starved Rock State Park is the main attraction, known for adventure activities. In fact, it is said that rafting on the rapids of Vermilion is an unforgettable experience.

Lake Geneva

Just two and a half hour drive from Chicago is the resort town of Lake Geneva which makes for a perfect day trip. Some of the popular watersports here are canoeing, paddleboarding, and kayaking. 

This fun family getaway has a zoo and a great entertainment center in the Timber Ridge Lodge & Waterpark. The long up and down drive notwithstanding, Lake Geneva is an ideal one day getaway from Chicago.

Pullman National Monument

A good way to spend the day and explore the South Side neighborhood is by visiting the Pullman National Monument some 24 km or 15 miles away from Chicago. 

Here in this historic district, you will come across Chicago’s one and only national monument designated by ex-President Obama in 2015 designed by George Pullman, the railcar tycoon.

The place also features Hotel Florence and National A. Philip Randolph Pullman Porter Museum with its unique architecture and wide open grassy spaces.

Sightseeing Map for Chicago Itinerary 2 days

Additional tips for Chicago 2 day itinerary 

Here are a few additional travel tips for Chicago.

Book tickets ahead of time
Remember to book attractions ahead of time. Save time and money by opting to see any three or all of the five most important attractions in Chicago with the Chicago CityPass which allows you to skip lines, gives sightseeing advice and discounts on shopping and entertainment.

Is Chicago safe – Safety Tips 

Chicago may have been the one time stomping ground of the legendary gangster Al Capone, but is now a relatively safe city to roam in, petty crimes notwithstanding. 

The River North and North Michigan areas are crowded during the evening, while the Grant Park and Loop are nearer to the museums. Here is some information on how to keep your wits about you in the third largest city in America.

• Keep your valuables hidden from sight and belongings close to you.
• Limit the amount of cash you carry
• Be vigilant on public transport and popular tourist sites where thieves mostly operate.
• Don’t follow Google Maps blindly. Confirm with a local if you are visiting a potential risky area.
• Don’t enter the Loop at night as it gets quite isolated.
• Research your accommodation before you go, as picking the right area is the key.
• Ask for help from the local hotel or hostel owner on which spots are safe.
• Let your family and friends know where you are.
• Do not display gadgets and cell phones as these are the primary targets of theft these days.
• Even though your trip is for two days, never forget to take travel insurance before you leave your home. World Nomads and SafetyWing are some of the best for providing Chicago Travel insurance.

2 day Chicago Packing List

• Comfortable boots or shoes: You will be doing quite a bit of walking so wear a good pair of shoes or boots which won’t slow you down as you have only a couple of days to explore the city.
• Adapter with power bank: This is an absolute must if you want to stay connected at all times on your trip to Chicago.
• Reusable water bottle: Be kind to the environment and carry a reusable water bottle to stay hydrated instead of using plastic bottles.

How is the traffic and transportation like in Chicago

For a quick weekend trip, use the bus and the elevated train (the L) network to see the neighborhoods and the suburbs. Between these, you can access almost any point of your two days stay in Chicago.

Ditch the car as traffic is heavy and gas and car rentals are expensive (unless if you are on a road trip).

Use the Chicago Transport Authority El trains to and from the airports. The Blue Line serves O’Hare while the Orange Line is for Midway International Airport.

Download some of the important apps like Google Maps, Uber, and Lyft to help you get around at any time of the day or night. For real time projection of buses and EI trains, the Transit App is the best.

The city is laid on a solid grid system, unlike many other American cities. Do check neighborhoods on Google Maps to get a gist of it for getting around.

Tipping in Chicago 

Tipping rates in Chicago are the highest anywhere in the country. It is 20% for a meal at a sit down restaurant. When ordering a drink from the bar, a dollar per drink is considered fine.

Keep some cash in hand as many cheap eats and dive bars do not accept credit cards.

We hope you found this post on a Chicago weekend trip useful in planning yours. Have more questions, let us know in the comments!

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