It is impossible to cover all of Chicago in one weekend, but that doesn’t mean you can’t get a taste of it. This 48 hour itinerary will help you discover some of the city’s best restaurants and top attractions.

Day 1

8:00 a.m.

Enjoy a hearty breakfast at your hotel. You’ll be needing your energy for a busy day ahead.

Coud Gate Chicago

9:00 a.m.

Start your morning by visiting the city’s most iconic landmark: Cloud Gate. The bean-like art installation is the work of Anish Kapoor and visitors enjoy snapping photos on the reflective surface. Go on, take a selfie!

9:30 a.m.

After visiting Cloud Gate, you should spend some time exploring Millennium Park – there are plenty of interesting art installations to see! Grab a seat by the Crown Fountain and admire the work of Spanish-born artist Jaume Plensa. The fountain consists of two towers that project the faces of numerous Chicago citizens. The Jay Pritzker Pavilion is also located in Millennium Park and during the warmer months it hosts a number of free events including concerts and movie nights.

Field Museum Chicago

10:30 a.m.

Make your way to the Field Museum where you’ll meet Sue. She hangs out in the main hall and she’s quite the looker for a 65 million-year-old (give or take) Tyrannosaurus rex.


You’ll be hungry after your visit to the Field Museum, so why not grab some lunch? We suggest Perry’s Deli. They are said to carry the biggest and best sandwiches in Chicago, and they have everything from roast beef to sugar-cured bacon!

Navy Pier Chicago

1:30 p.m.

After lunch, head on over to the Navy Pier. This Chicago landmark is undergoing some expansions, but you can still enjoy some shopping, performances, and rides.

3:00 p.m.

You have a long night ahead of you, so why not head back to your hotel for a quick nap; it’ll be dinner time before you know it.

Pizzeria Uno

6:00 p.m.

Where to find the best pizza in Chicago is a highly contested topic, however, after eating my way around many of the city’s pizzerias I can say that my personal favourite is Uno Pizzeria. Their specialty pizza, Numero Uno, is a heavenly combination of sausage, pepperoni, onions, peppers, mushrooms, chunky tomato sauce and mozzarella. Just a heads up, make a reservation in advance or be prepared to wait upwards of an hour for a table on a Saturday night.

8:30 p.m.

Head up 360 Chicago at the John Hancock Centre for a dazzling look at the city all lit up at night. You may want to check the Chicago weather forecast in advance; unpredictable fog can spoil the view.

11:00 p.m.

Craving a good laugh? There are numerous comedy clubs in the city but the most famous of them all is Second City. Weekend tickets are a hot item so be sure you get yours well in advance.

12:15 a.m.

Finally get back to your hotel and pass out for the night. There are plenty of Chicago hotel deals to be had.

Day 2

10:30 a.m.

You’re beat from the previous night’s outing, but food can fix that! Head over to Lou Mitchell’s for the best brunch in town. The omelettes here are amazing, but the thing I love the most is that they let you munch on donut holes while you wait for your breakfast to be made.


Hop on a river cruise for a tour of Chicago’s architecture. Chicago’s First Lady offers 90 minutes cruises with commentary. These run between April to November; you wouldn’t want to be out on the water any later in the season, after all, this is the Windy City.

1:30 p.m.

You’re still too stuffed from brunch, but you’re starting to feel a little peckish. Grab yourself a Chicago-style hot dog from a street vendor to enjoy on a park bench. Remember, you can put all kinds of toppings on it, but no Chicagoan in their right mind would add ketchup to theirs!

Art Institute of Chicago

2:00 p.m.

Make your way over to one of the city’s most-famed museums, the Art Institute of Chicago. The American art collection is particularly interesting and it includes works by Georgia O’Keeffe, Edward Hopper and Grant Wood. Also, make sure you don’t miss the Thorne Miniature Rooms located at basement level. The collection features intricate models of European and American home interiors and it’s a fascinating window at the way people lived just a few centuries ago.

4:30 p.m.

Next, why not head over to Intelligentsia Coffee to recharge with a cup of java. This local coffee chain knows how to make some good coffee and they now have 7 locations across the city.

6:00 p.m.

If it’s baseball season and the Cubs are in town, then you have to catch a game at Wrigley Field. The Chicago Cubs certainly aren’t known for their winning streak – they haven’t won the World Series in over 100 years – but they are a loved team and people come and cheer them on anyway.

8:30 p.m.

For a unique dinner on your last night in the city head over to Alinea. This place is much more than a restaurant; it is a dining experience that showcases anywhere between 18 and 22 courses. It has thrice been named the best restaurant in the United States, and it’ll be an experience you won’t soon forget. They don’t accept walk-ins so reserve your ticket well in advance in order to avoid disappointment.

10:45 p.m.

Enjoy one last sleep in the city and start dreaming of your return!

What are some of your favourite Chicago attractions?