A 2 day Chicago itinerary to help you make the most of your weekend in the city

We recently spent a weekend in Chicago as part of a trip across the US. It was our first stop after a 9 hour flight from Zurich and our first taste of the US. Overall we spent 2 days in Chicago which gave us the opportunity to get acquainted with the city. But it also left us wanting more.

We went in to Chicago not knowing what to expect. The cities history has always intrigued us, with this idea of gangsters and prohibition style bars very much at the forefront of our minds.

But Chicago is so much more than that. It’s a cultural hub, with so many museums, theatres, and some incredible architecture. And it’s also the perfect place for a US city break.

In this guide we help you plan how to see Chicago in 2 days, with top tips on where to stay, what to eat, and what to do. 

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2 days in Chicago – Some Background 

Located in the US state of Illinois Chicago, or the Windy City as it is often referred to, is the 3^rd biggest city in the US in terms of population. Famed for its deep dish pizza and 1920’s gangsters it is a fantastic city to come for a weekend break. It has a population of around 2.7 million and is an incredibly multicultural place.

Wondering if Chicago is worth visiting? Here is a handy guide.

2 days in Chicago- Getting Around

When planning your 2 day Chicago itinerary it is important to know how to get around. Public transport in Chicago is pretty easy to navigate. You can purchase a daily pass that will allow you travel on the buses and trains throughout the day.

The trains known as the L, are speedy and especially if you are travelling around the downtown loop you will get some amazing views of Chicago as the tracks are often elevated. In fact you might want to just get on and stare out the window (which we actively encourage).  

You can purchase passes for 1, 3, 7, or 30 days and these will enable you to travel on all trains and buses in the city. Despite only being able to see Chicago in 2 days, we opted for the 3 day pass for $20, which was really good value considering a 1 day pass is $10. We recommend having a look at the Chicago Transit Authority website for more detailed information. We purchased our passes at the train station near our hotel and these got us through our 2 days in Chicago.

You will need to get a Ventra Card in order to load your pre-paid passes. This costs $5 but this amount is refundable when you return the card. Apart from public transport Chicago is pretty walkable. Most major tourist attractions are within walking distance of each other, making it pretty easy to navigate your way across the city during your Chicago weekend trip.

Another way to get around Chicago is to book on a Hop on hop off tour. Tickets are valid 1-2 days depending on the purchase and you can visit the main sights whilst admiring the views from the top of a double decker bus.

Where to stay for your 2 days in Chicago

On all honestly 2 days in Chicago isn’t a whole lot of time, therefore if you are able to, we recommend staying in the downtown area. You will be close to a lot of tourist attractions as well as restaurants and bars.

When you only have 2 days in Chicago, this definitely helps. But if you are looking for cheaper alternatives you will need to go a bit further out.

We ended up staying the in medical district because we decided to book our weekend in Chicago at the same time as the Chicago marathon. Needless to stay accommodation was really expensive and a lot of it had sold out. This wasn’t ideal as there aren’t that many bars or restaurants in the area. If you do stay further out then we recommend making sure you are close to public transport as it will make it so much easier to get around.

Here is a breakdown on some of the best areas to stay for your 2 days in Chicago.

The Chicago Loop

The best area to stay for your 2 days in Chicago without a doubt is the Chicago Loop. This is essentially the central downtown bit of the city. Here you are close to a lot of the main attractions like Millennium Park and the Art Institute of Chicago.

It’s also a great area in terms of bars and restaurants, meaning you will never be bored. Accommodation tends to be a bit more expensive, but that isn’t surprising due to its central location.

West Loop

The West Loop is another viable option for visiting Chicago in 2 days. It has become the trendy part of Chicago and is the former meatpacking and warehouse district.

The West Loop is great if you fancy yourself a bit of a foodie. There are so many fantastic restaurants and food places including Restaurant Row, and the French Market. It’s also great for nightlife.

Magnificent Mile

The Magnificent Mile, is the perfect area to stay in Chicago for shoppers. There are so many high street and boutique stores, that you could pretty much spend your full 2 days in Chicago shopping. It’s close to sights like the John Hancock Centre as well, with great transport links to other attractions.

Admittedly hotels around here are a bit on the pricey side, so do keep that in mind. It also gets busy and congested at certain times.

2 days in Chicago – Getting from O’Hare Airport to your hotel

Your Chicago weekend trip starts as soon as you land at the airport. From here there are a few ways to get to the downtown area. The cheapest and quickest way to get downtown is via the L Train. The Blue Line should have you in the downtown area in approximately 45 minutes.

If you are however, severely jet lagged and the thought of negotiating a subway line with giant suitcases scares you (you are not alone), then the next best thing is to get the airport shuttle bus.

They are slightly cheaper than a taxi and take you straight to the front door of your hotel. Just be mindful that the journey can be quite long, particularly during peak hour. It took us well over an hour just to get to the downtown core due to the traffic.

You can book and pay for your shuttle at one of the designated booths at the airport. The good thing here is that you can pre-book your return trip to the airport too. Once you know the time you want to leave you can call the company to arrange your pick up from your hotel back to the airport.

If you want to be super fancy you can always book a private airport transfer here.

Weather in Chicago

Chicago’s weather definitely gives you the chance to experience the seasons in full. The summer months are hot and often humid ranging from 20-30 degrees Celsius. They are usually dry but expect a few days of rain here or there. The summer months are June, July, and August. Summer is probably one of the best times to visit especially considering the weather is so good making it ideal for exploring the city.

What to pack for your 2 day Chicago itinerary – in summer

• Hat
• Sunglasses
• Cool clothes
• Cardigans – it can get cooler sometimes at night
• Good walking shoes

In the winter the weather takes a very cold turn. In December, January and February, expect a lot of snow and ice. The weather ranges from around 3 to -8 Celsius as an average.

What to pack for your 2 day Chicago itinerary – in winter

• Thermals
• A really good coat
• Snow boots/ winter boots
• A good scarf and pair of gloves
• Thick socks

Best time to plan your 2 days in Chicago

The best time of year to visit Chicago is around April and May or September and October, Temperatures are warm but not overly warm and tourist season starts to dwindle, making accommodation cheaper.

Winters in Chicago can be quite harsh with a lot of snow and freezing temperatures. This will obviously limit the amount of things that you are able to do so we would rule this out. I mean when you only have 2 days in Chicago you really don’t want to be spending all that time in the cold!

The summer months in Chicago tend to be busy with tourists. If you do visit at this time of the year make sure you book things well in advance to get the best prices.

Is 2 days in Chicago enough?

You might be wondering whether 2 days in Chicago is enough time to see the city. Admittedly we felt like we could have done with so much more time here, so would say that 5 days is probably the ideal amount of time. This gives you a chance to explore more of the neighbourhoods and venture out of the downtown area.

That being said if you do only have 2 days in Chicago all is not lost. This will still allow you ample time to see the sights, eat some incredible food, and treat yourself to a cocktail or two. A lot of the major attractions are in the downtown area so you won’t have to do a lot of travelling to get around. The main thing is to be organised and plan your 2 day Chicago itinerary in advance to make the most of your time there.

2 days in Chicago – Things to do

Here are some of our recommendations of things to do when you only have 2 days in Chicago.

☁ Do the Riverwalk

The Riverwalk is a must for any 2 day Chicago itinerary and in our opinion one of the most beautiful things to do in Chicago. It is a 1.25 mile long promenade filled with outdoor bars and cafes, and as you’d expect it goes right along the river. The adventurous among you can rent bikes or kayaks, whilst the rest of us can just walk along taking in what has to be one of the most beautiful parts of the city.

You can book a self guided Riverwalk tour here.

☁Take an Architecture Cruise

One of the first things in Chicago that draws you in, has to be the buildings. I know New York or any other big city has tall skyscrapers, but there is something much more intriguing and beautiful about Chicago. You look up and you really want to know more. Luckily there is a cruise that can answer all your burning architecture questions. You can either book your cruise beforehand or book on the day. We went with First Lady cruises, located along the promenade.

 It cost around $43 plus tax, which might sound steep but we felt it was worth it. The tour lasts around 1.5 hours, and you get an in depth guide into the buildings that make Chicago what it is today. It is a good way for you to orient yourself with the city, so make sure you add this to your weekend in Chicago. 

Below are some tours you can pre-book online. It is probably worth doing because these cruises do get really popular.

☁ Do a gangster tour

When you think of Chicago one of the first things you might think about is Al Capone or gangsters. The city certainly has a very colourful past, with the likes of John Dillinger and Al Capone, running things back in the day. So a Mob/Crime tour is a must in Chicago.

You get to ride around the city and see some of the most famous mob spots with a professional and knowledgeable guide. I actually did this tour many moons ago and it was one of my highlights in Chicago, so it is worth adding to your 2 day Chicago itinerary.

And if gangsters are your thing why not check out our itinerary for Vegas to learn about their history in the USA.

☁Explore Navy Pier

One of Chicago’s most popular attractions has to be Navy Pier. If you follow the signs across the Riverwalk you will start to lose sight of the looming skyscrapers and reach Lake Michigan.

The real appeal of Navy Pier is that there is a little something for everyone. From rides, to restaurants, to the Shakespeare Theatre, there is an eclectic mix of activities for the whole family. There are also outdoor bars with some unreal views of the city.

Unfortunately for us, when we visited during our 2 days in Chicago we got to see why they call it the windy city. The weather wasn’t really working in our favour, but we did not let that stop us.

We sat near the water, Dave with a beer in hand, and me with a fruity cup of Sangria, as the rainclouds loomed in the distance. And despite the fact that we couldn’t put our drinks down for fear they would blow away, we had a great time gazing up at the Chicago skyline.

One of the top attractions at Navy Pier is the Centennial Wheel. From here you get a 360 degree view of Chicago’s iconic skyline, and if you order tickets online in advance you can also skip the queue.

☁Do a street art tour

If you are looking for something a bit different why not add a street art tour to your 2 day Chicago itinerary. You can visit some of the city’s coolest neighbourhoods and the artists who create the work.

☁Do a ghost tour

Another fun thing to add to your 2 days in Chicago is a city ghost tour. You can visit the most haunted spots in Chicago and learn all about the history of these places.

☁Visit The John Hancock Centre

One of two observation buildings in Chicago, we recommend you visit the John Hancock Centre about an hour before sunset. Be prepared for queues, unless like us you arrive on a day the ticket desk clerk called “the foggiest he had ever seen”.  So we found it pretty much deserted.

We debated about whether or not to go up, but considering we were only in Chicago for 2 days decided to go for it. It’s $25 to go up and that does include a cocktail from the bar (tickets are slightly cheaper if you want to skip the drink). There are quite a few places to sit and enjoy the view, or in our case fog, whilst sipping a drink and looking out from the 94th floor.

The observation deck is actually called 360 Chicago, mostly for the 360 degree views you get of the city (we assume). It is also home to TILT which is a thrill ride that essentially tilt’s you slightly. I know that doesn’t sound like the most exciting thing, but I was too terrified to even think about doing it.

We do recommend booking your tickets in advance online so that you can skip the queue. 

☁Admire The Views From The Willis Tower

This is another must for your Chicago weekend trip. We visited the Willis Tower first thing in the morning and did not regret it. The tower opens at 10am so if you get there at least 30 mins before this, you have a chance of being one of the first groups up the tower for the day.

For us it was fantastic because we got to spend a bit of time on the clear observation boxes before the crowds arrived. This is another one that we highly recommend you book in advance. 

☁Take Selfies In Millennium Park

There is nothing that says Chicago more than taking a reflection selfie with the Bean in Millenium Park (at least according to our Instagram feed anyway). Designed by Anish Kapoor this 110 ton silver sculpture perfectly reflects the Chicago skyline, and seems to be a real favourite amongst visitors to the city. Don’t forget about the rest of the park though. It is like a small garden oasis in the middle of the bustling city. It is also one of the best photo spots in Chicago. 

The park fountains are also worth a visit. There are two 50 ft towers  with video footage of different faces. Apparently these are all faces of native Chicagoans, and they pucker up and spit water every so often. We found a lot of families gathered around here, with kids splashing around in the water trying to keep cool.

☁Visit the Chicago Theatre

The Chicago Theatre is one of the most iconic buildings in the city. Whether you stop by to take a photo, or do a tour of the inside, you have to add this to your list of things to do in Chicago. If you have time a guided tour of the theatre is recommended as the inside is beautiful.

☁Get Cultural At The Art Institute of Chicago

A short walk from Millennium Park and you will find yourself at the Art Institute of Chicago. Our Lonely Planet guide lists this as the top thing to do in Chicago so it really is worth a visit. It is the second largest art museum in the country and houses collections from around the world. The highlight for me was seeing artwork by Andy Warhol, but you will also see works by Picasso and van Gogh.

If you are wanting to skip the line and do a guided tour you are best of buying tickets online in advance.

☁Visit Wrigley Field

If you like baseball or not Wrigley Field is still worth a visit. It is the home of the Chicago Cubs and has been since 1914 when it was known as Weeghman Park. In 1927 Wrigley’s chewing gum bought the rights to the stadium and hence why it is know as Wrigley Field to this day. You can do stadium tours or if you arrive during baseball season you can even catch a game.

Eating and drinking during your 2 days in Chicago

☁Visit A Speakeasy

Like us if you have packed a lot into your 2 day Chicago itinerary you might be in desperate need of a drink. And let’s face it exploring a city can be thirsty work, so you should head over to the Green Door Tavern for a few drinks. Chicago has a fascinating history, particularly in the prohibition era so a visit to a speakeasy is a must.

The reason for the name is because in the prohibition era if a tavern door was painted green this meant the presence of a speakeasy. There are a lot of historical speakeasies in the city and some are even famed for being the hangouts of mob bosses such as Al Capone, although these tend to be located away from downtown Chicago.

SPEAKEASY FACTS

• As a direct result of prohibition bootlegging and organised crime became commonplace in the USA.
• Speakeasies were designed as a way for gangsters, the wealthy and everyone else to come together and drink.
• They usually claimed to sell coffee or were located in attics, basements, office buildings and even private homes.
• There were over 7000 speakeasies in Chicago during their peak in the 1920’s.
• Speakeasies were attributed to the birth of jazz music.

One of the cooler tours to add to your 2 day Chicago itinerary has to be a speakeasy and cocktail VIP tour. It gives you a real taste of prohibition era Chicago. It’s an expensive tour but if you have a group of 5 it is so worth it. And if you do it, please take us along!!!!!!!

☁Munch On Some Deep Dish Pizza

You cannot, I repeat, CANNOT leave Chicago without trying the legendary deep dish pizza. There are a number of places throughout the city that serve the famous dish so take your pick.We ate at Pizano’s and we loved it.  As the name suggests the pizza crust is quite deep allowing for a lot of cheese and fillings. It was one of our favourite meals on our trip the US, so we do recommend it.

DEEP DISH PIZZA FACTS  

• Deep dish pizza was only invented in 1943 and there is some dispute as to who officially created it.
• Due to its thickness the deep dish is layered completely differently to a regular pizza. For starters the cheese goes first then the toppings then finally the tomato sauce. This is done to stop the cheese burning as the cooking time is a lot longer than for a regular pizza.
• Pizzeria Uno in Chicago was the first place to serve deep dish, and the trend continued with a number of places serving it today.

Apart from deep dish pizza Chicago is a real foodies paradise. In fact something we recommend during your 2 days in Chicago is to do a food tour. Have a look below at some great ideas.

2 day Chicago itinerary

Here is our 2 day Chicago itinerary to act as a guide for your own trip to Chicago. 

2 day Chicago itinerary – Day 1

We recommend starting your weekend in Chicago by doing the Riverwalk. It is a really beautiful part of the city and a great starting point for your trip. While you are here book an architecture cruise, and spend the rest of the morning floating down the Chicago river admiring the buildings. If you are a bit of a thrill seeker (unlike us!) then you could rent a kayak and explore the river at your own pace.

After the tour head down to Navy Pier for some lunch and a beer by the water. It is a great place to explore and there are a lot of rides and restaurants to keep you entertained.

As evening approaches head to the John Hancock Centre for some incredible views of the city, and have a drink at the bar as you watch the sunset for the day. Once you are done there are a number of restaurants in this area for dinner and drinks.

2 day Chicago itinerary – Day 2

On day 2 of your Chicago weekend trip we highly recommend making your way over to the Willis Tower. On the way if you have time to look around Union Station do. The architecture is incredible and you might recognise it from being in various movies. The reason we recommend visiting Willis Tower first thing is because if you are one of the first lots of people to go up you can appreciate the view before it becomes full of tourists.

Afterwards head over to Millennium Park take take your all important Chicago Bean selfie. Do make the time to explore the park, especially the modern water feature. If you are hungry then head out for some deep dish pizza. This is a must when visiting the city.

After lunch spend your afternoon exploring the Art Institution of Chicago, before heading to the Green Door Tavern for a drink.

Romantic things to add to your 2 day Chicago itinerary

If you are lucky enough to visit Chicago with your significant other, here are some of our top suggestions for romantic things to add to your 2 day Chicago itinerary.

Dinner cruise

What could be more romantic than enjoying a dinner or evening cruise on Lake Michigan. The views of the skyline are incredible, and you get the opportunity to sip drinks, and enjoy some food as you sail along the tranquil waters.

Chicago Theatre

Yes it is totally cliched but attending a show at the Chicago theatre is certainly one of the more romantic things to add to your 2 day Chicago itinerary. This French baroque style theatre is pretty much iconic in Chicago!

Enjoy some cocktails at a height

Chicago is an exciting city, and even more so at night when it is lit up and bustling. So one of the most romantic things to do during your 2 days in Chicago, has to be sipping cocktails from a rooftop bar. Cindy’s is one of our favourites, with some great views from its rooftop balcony.

Aire Ancient Baths

If you fancy a bit of pampering we recommend visiting Aire Ancient Baths. Located in a restored factory dating back from 1902 here you will find 6 thermal baths, a pool, saltwater floatarium and more. Also consider booking in for a couple’s massage.

Do a helicopter tour

Another romantic thing to add to your 2 days in Chicago has to be a helicopter tour of the city. You get to experience Chicago from a height, and get a unique perspective on the city.

Night tours

There are some really cool night time tours you can add to your 2 day Chicago itinerary to experience the city at its most romantic time, which is the evening. All the city lights create the perfect backdrop for an evening of romance.

How much money do I need for my 2 days in Chicago

You might be wondering if spending 2 days in Chicago is going to break the bank or not. Chicago is an expensive city, although good news it is slightly cheaper than say New York City.

Accommodation in Chicago can be expensive. Especially if like us you visit in the middle of the Chicago Marathon.  An average night in a hotel will probably set you back somewhere between $150-$300 but this will of course depend on location and amenities.

Food isn’t too bad at about $35 for an average dinner meal per person. Again this depends on what you want to eat though (and don’t forget to tip).

We would say you probably want to budget about $500 for the 2 days in Chicago per person not including accommodation. This will cover you for transport, entry to tourist attractions, food, and a few cocktails among other things.

2 day Chicago itinerary – a recap

Hopefully this guide will help you plan your own 2 day itinerary in Chicago. It really is an incredible city and the longer you can spend here the better. But if like us you only have 2 days in Chicago you really can make the most of it and explore the city in a limited time as long as you plan in advance what you want to do. Don’t forget to pin this guide for later, and enjoy your 2 days in Chicago!