Oh the Windy City! Are you ready to have a whirlwind 48 hours in Chicago?! There are plenty of things to do that 2 days in Chicago is nowhere near enough but its a start. Below is the perfect Chicago itinerary to make the most of your time in the city. I have put together a fun guide to make the most of your two days in Chi-Town!
You will get a little mix of history, architecture, nature, and of course some great bites and sips along the way. Tips on where to stay in Chicago, places to visit, best time to visit and make the most of your time in Chicago.
There are also plenty of tours in Chicago that help you maximise your time and budget. From hop-on hop-off tours, food tours, river cruises and more.
How To See Chicago In 2 Days – What To See Do And Eat
Day 1 In Chicago
Assuming you arrive pretty early in the day to Chicago O’Hare (ORD) or Chicago Midway (MDW) then you can hit the ground running. Luckily both Chicago airports offer a lot of direct flights from most major airports around the country.
In Chicago, I’d recommend not getting a rental car and instead take public transit like the subway, taxis or Ubers and walk as many of the attractions and places are walkable!
This is the perfect location to be based out of because you can walk to so many restaurants, bars, lounges, and other attractions. The DoubleTree is modern, clean and very well updated with all the latest amenities and updated in the latest trendy styles.
After you get checked in and freshen up as need be, time to find some nourishment… brunch! Here are a few great options in walking distance:
- Wildberry Pancakes and Café. Obviously they have great pancakes, but they also have other breakfast and brunch staples to fill you up!
- Beatrix. They have a wonderful brunch menu for both traditional and new cuisine.
The hotel’s convenient location on the Magnificent Mile is a great excuse to get out and get some steps and shopping in! The Magnificent Mile is considered an upscale section of Chicago’s Michigan Avenue which has all your shopping desires. Spend some time bopping into the different shops along the way and get in your retail therapy.
As you make your way down the Magnificent Mile, you’ll want to head in the direction of Millennium Park and the Art Institute of Chicago. Luckily Madison Avenue will lead you super close in that direction, close to the Crown Fountain. It’s about a 1-mile stroll but provides a lot of things to stop and see along the way so it’s worth it.
Once you get to Millennium Park there are a lot of options of things to see. First off, you have to go to ‘the bean’ and get a picture – it’s like a necessity when you visit! There are tons of beautiful gardens and walking paths in the park so take your time and enjoy the little oasis in the city.
Within Millennium Park is the Art Institute of Chicago which is one of the largest and oldest art museums in the country! It holds some incredibly impressive collections of the world’s most famous artists like Picasso, Van Gogh, Monet and Rembrandt.
The building is impressive in and of itself, dating back to the 1890s for the World Fair. You could easily spend many hours here, so you may want to pick and choose what exhibits and styles you’d like to visit.
After your art education, you’ll probably want to grab some lunch as you head towards the water. Here are a couple options for lunch:
- Miller’s Pub. An all-American restaurant with everything from beer, to steaks, to salads and everything in between.
- Lou Malnati’s Pizzeria. Probably one of the most iconic deep-dish pizza joints in downtown Chicago.
After all that walking, it’s time to take a seat. Hop on one of the architecture river cruise boats and cruise down the Chicago River and see some of the city’s most famous architecture by water! This 1-hour guided tour will give you lots of information about the history of Chicago, its buildings and its unique culture.
The boats are equipped with restrooms and even better – a full bar! Cruises run daily from the Navy Pier and Michigan Avenue and tickets can be purchased online or in person. This is a great way to catch the beauty of the sunset and dusk in the Windy City.
Slip back to the hotel to change and freshen up and head out for a late-night appetizer or lite dinner and cocktails. Finish off your first day in Chicago at one of the following great eats:
- Cindy’s. Great appetizers and cocktails with a spectacular view of the city.
- London House (LH) Rooftop. Another fabulous eatery on the rooftop offering epic views of downtown Chicago.
Day 2 In Chicago
Your second full day in Chicago is packed, so start off with a filling breakfast to get the day started right. A few great options for breakfast are:
- Do-Rite Donuts & Chicken. If you’re looking for a quick grab-and-go chicken sandwich or a donut, then this is your spot to stop and go.
- Egg Harbor Café. A little more traditional and sit down, this place offers everything you want for breakfast and brunch.
Your first itinerary item of the day is going to the Willis Tower, what used to be the tallest building in the world. At 110 stories tall, this is one of the iconic buildings of the Chicago skyline.
The Skydeck.is located on the 103rd floor of the Willis Tower and offers quite possibly the most spectacular views of the city and beyond. On a clear day, you can see up to 50 miles out which means you can see Illinois, Indiana, Michigan and Wisconsin!
If you really want to live on the edge, or should I say ‘ledge’, then gather your courage and step out on the glass ledge that juts out beyond the building, allowing you a 103 floor view straight down to the busy streets of Chicago.
You can pre-purchase tickets online or get them on-site however it’s a very popular attraction so get there early, even before the doors open if possible to avoid super long lines.
After taking your daredevil self for a spin, you can walk or take public transit to The Lincoln Park Zoo. Home to more 200 species and 1,100 animals, the zoo is full of endangered, exotic and native animals. They have penguins, polar bears, gorillas, and kangaroos just to name a few. Plan for a few hours here and grab lunch at one of the little cafes throughout the park.
Next, keep walking further north, or take an Uber or taxi and at least stop by Wrigley Field to appreciate its history and beauty. The field is really neat, even if you’re not a huge fan.
It would be awesome if it worked out if a game was going on while you were visiting; if there is, it’s definitely worth grabbing a few tickets and making a night out of hotdogs, popcorn and America’s pastime.
Located around the field are lots of sports bars and pubs to pop in and grab a pint while you’re out too, and most have some great memorabilia of the field!
You’ll want to take an Uber or taxi back towards town and for the final stop of your trip should be taking in Navy Pier. The Navy Pier is one of those iconic Chicago landmarks you need to visit.
It has little shops to purchase souvenirs, cafes and restaurants and even has a few small amusement ride for kids. Walk along the pier and the riverfront and enjoy your last few hours in downtown Chicago soaking up all the glory of the Windy City!
Best Time To Visit Chicago
My brother lives only a couple of hours drive from Chicago and I have seen enough pictures from him to know that winter is not the best time to visit Chicago! They can sometimes get ridiculous snowfall making exploring close to impossible.
So if you are heading to visit as a ‘tourist’, that is definitely not when you want to visit the city. Instead, the best time to visit would be, summer and Autumn. Also note that spring in Chicago can be unpredictable. Below are details on Chicago weather.
Spring: Spring in Chicago is perhaps the city’s most unpredictable season: Winter can last until April or even May. Thunderstorms can occur any time of the year, but are most prevalent in the springtime as the city’s central location within the United States, as well as its lakeside location, makes it a center of conflicts between large volumes of warm and cold air, which can trigger a wide variety of severe weather.
The most severe storms can contain large hail, damaging straight-line winds, flooding, and tornadoes. Temperatures vary tremendously in the springtime; at 100 °F (38 °C), March is the month with the greatest span between the record high and low. At O’Hare, temperatures as low as 7 °F (−14 °C) and 31 °F (−1 °C) have been recorded as late as April 7 and May 21, respectively.
Summer: On a typical summer day, humidity is usually moderately high, and temperatures ordinarily reach anywhere between 78 and 92 °F (26 and 33 °C). Overnight temperatures in summer usually drop to around 65–70 °F (18–21 °C), although even in July and August there can be several nights where the temperature drops below 60 °F (16 °C), particularly during the cooler summers.
Conversely, on the other extreme, temperatures can on a rare basis remain above 80 °F (27 °C) overnight, though this level of overnight warmth is generally limited to the city proper with its urban heat island effects along with Lake Michigan nearby.
Autumn: The extreme heat that Chicago is capable of experiencing during the height of the summer season can persist into the autumn season. Temperatures have reached 100 °F (38 °C) as late as September 7 (with 99 °F (37 °C) occurring as late as September 29), and temperatures have reached 90 °F (32 °C) as late as October 6, which occurred in 1963, with a temperature of 94 °F (34 °C) on that day.
Conversely, temperatures have dropped below freezing overnight as early as September 23, and temperatures below 0 °F (−18 °C) have arrived as early as November 23.
How To Get Around In Chicago – How To Get To Chicago
Getting Around Chicago: There taxis, Uber, intercity trains as well as the Chicago ‘L’ train system connecting the various suburbs of Chicago. I mostly used taxis, Uber and walking around Chicago during my stay.
How To Get To Chicago: While there are are plenty of ways to get to Chicago, my family and I drove to Chicago from Niles, Michigan. Its a few hours drive, we left in the morning and arrived with enough time to explore before my family went back to Michigan and I explored more of Chicago before leaving for Seattle a few days later.
You can also fly into Chicago by during this trip I flew out of Chicago so when it comes to transport from Chicago airport into the city that is fairly easy. I chose to take a cab to the airport to save time.
Where To Stay In Chicago
There are several areas to stay in Chicago and I will go into more detail in a separate post but for those on a short visit to Chicago, depending on your intentions I would recommend staying near Magnificent Mile. I found it easier to walk around to many of the tourist places and attractions as I stayed at Hotel Cass, a Holiday Inn Express Hotel. The location is just unbeatable and so were the rooms and food too. Close to everything you would want to see.
If you are of course staying longer than 2 days in Chicago, and in the city for nightlife and more of a local file then stay near Lakeview or Wrigleyville where there are plenty of nightclubs, bars and restaurants. Or stay near Lincoln Park where there are plenty of cultural attractions like the Chicago History Museum, ParkZoo as well as a bustling commercial street.
As I said I stayed close to Magnificent Mile but you can find plenty of hotel options in Chicago from budget hotels to luxury hotels to suit your budget. For an extensive list of hotels in Chicago, click here.
Recommended Reading For Chicago Travel Tips
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