2 days in Chicago – Day 1

The ‘windy city’ or ‘Chi-Town’ is one of my favorite cities in the US. And with just 2 days in Chicago to spend, I wanted to pack in as much as possible. 

After an 8-hour flight from London, I arrived in Chicago’s O’Hare Airport with no polar vortex in sight. Like most places in spring, Chicago is pretty. Full of promise in the air, springtime is ideal for walking and taking in the sights. 


2 days in Chicago - Fashion Outlets of Chicago is right by the airport

2 days in Chicago – Fashion Outlets of Chicago is right by the airport


After surviving the long and tiring trek through US customs and immigration, I was happy to see the other side of the terminal building. I met my brother, who lives here, and we wasted no time in heading to our first destination.

The Fashion Outlets of Chicago – 2 days in Chicago

The Fashion Outlets of Chicago is approximately 10 minutes from the airport. It’s a mecca for designer as well as bargain shoppers.It might sound like a strange place to start, but it’s so close to the airport, so why not?

Despite my general feelings about the soulless shopping mall experience, I was pleasantly surprised once inside. The upper level caters to high-end designer stores like Gucci and Prada, while the lower level satisfies a more humble wallet.

Three hours and a few bargains later, we left Rosemont, and made our way to my favorite neighborhood: Wicker Park. I highly recommend first-timers to the city to consider booking a local tour. They’re a fun way to meet other travelers, and the local guides really know their stuff!





The Chicago ‘L’

With 2 days in Chicago, you don’t want to spend your time stuck in traffic. The fastest and cheapest way to head downtown — particularly during the rush hour — is the Chicago ‘L’. Trains arrive every 2 to 3 minutes, and you can take some pleasure watching the traffic from the train. We took the blue line to Damen, the train station at the heart of Wicker Park. 


Damen train station: the stop for Wicker Park

Damen train station: the stop for Wicker Park

2 days in Chicago: Wicker Park

I fell in love with Wicker Park the first time I visited in 2011. The independent boutique shops, and many bars and restaurants reinforce the area as a much-loved part of town.

The neighborhood combines a perfect mix of individuality with a sense of community. Wicker Park is known for being a little bit on the ‘hipster’ side. I didn’t really see anything I considered ‘hip’, but it might have something to do with the way the residents dress. Hipster or not, you feel like a local spending time in Wicker Park, and you get to see another side to the city.


Wicker Park: the sights

Goorin Bros Chicago (1533 N Milwaukee Avenue) is a quaint hat shop about a 3-minute walk from Damen station. Established in 1895, the ultra friendly staff is on hand to help and talk you through the beautiful selection of hats on offer. A charming shop front harking back to a past era, you’re purchasing an experience as much as a bespoke fedora.

A growling stomach brought me to the next spot in Wicker Park, Al’s Beef. Beef is big business in Chicago, and the thinly-sliced roasted beef drenched in its own juices in a sandwich bun is a mouth-watering treat.

2 days in Chicago - the Arcade Bar

2 days in Chicago – the Arcade Bar

With its nondescript shop front, the Arcade Bar is one venue you can easily walk past without taking a second look. It’s a novel kind of hangout and is also the perfect hub for a bit of nostalgic fun.

On one side is a long bar offering beers and spirits. On the other lies endless amusement in the form of arcade and pinball machines (ie Pacman and Tetris).

A weekend in Chicago – Logan Park

As night time fell, we moved to a nearby neighborhood called Logan Park. It’s 2 stops on the blue line from Damen to the nearest station, California. 

For dinner, we tried a German restaurant and beer hall called Das Radler. Reinforcing Chicago’s rich German heritage, the Radler’s surroundings were anything but. Mounted bicycles on the wall at the back, and contemporary Graffiti style prints give a modern edge to traditional Bavarian dining.

Rather than the traditional wurst, I chose the beer-battered perch with white beans and mussels. I followed this with a robust bourbon-based Shank’s Pony cocktail. Das Radler is sehr gut, and I can guarantee you won’t leave hungry or thirsty!

The Whistler

Last stop on day 1 was to a nearby bar called The Whistler (2421 N. Milwaukee Avenue). It’s a bar, gallery, record label and live music venue, but the main attraction is their extensive cocktail list. I chose a TV Funhouse, a tantalizing taste-bud concoction of rum, bourbon, cereal milk, honey and cinnamon.

‘Chicagoans’ are always been unbelievably chilled, and the crowd at The Whistler only exemplifies this. A lively atmosphere, friendly crowd and a Mexican guy selling Tamales inside, The Whistler is a great way to end day 1 in Chicago.


The Magnificent Mile – 2 days in Chicago


Weekend in Chicago: the beach at the end of the Magnificent Mile

Weekend in Chicago: the beach at the end of the Magnificent Mile


No trip to Chicago would be complete without heading downtown and taking a walk through Michigan Avenue. The locals know is as the Magnificent Mile, which is a name you’ll hear a lot when there.

The Magnificent Mile’s a main attraction for tourists for shopping as well as its many skyscrapers such as Willis Tower. It also has many famous shops such as Saks and Neiman Marcus in case you want to do some damage to the credit cards.

Perfect weekend in Chicago – North Avenue Beach

If shopping’s not your thing, there’s a better – and sandier – way to spend 2 days in Chicago. North Avenue Beach is at the end of Michigan Avenue and a regular go-to spot for locals.

Because it’s a city beach, it’s very easy to get there by bus or taxi. Though the temperature wasn’t quite being bikini weather when I was there, it’s still a great place to relax and reflect.

Lincoln Park

I passed the next few hours at Four Seasons Chicago for an indulgent 3-hour family brunch! To work off the excess, I went for a walk around Lincoln Park. On a sunny day, the Lincoln Park neighborhood and park is one of the best places to enjoy being outdoors.

The Lincoln Park Zoo in the park is open all year round. Entry is free, meaning there’s no reason not to pay a visit.


48 hours in Chicago - Cloud Gate a.k.a The Bean

48 hours in Chicago – Cloud Gate a.k.a The Bean

2 days in Chicago – Millennium Park

There’s no way you can spend a weekend in Chicago without visiting Millennium Park. It’s not only famous for hosting outdoor concerts, but it’s also the home of the Cloud Gate sculpture.

It’s commonly known as ‘The Bean’ and you can’t miss it given its size and the number of tourists. 

Chicago weekend – Apogee

The last stop on the Chicago 48-hour experience was a night out at Apogee. It’s a rooftop bar with an Asian-inspired menu with excellent American service. Quite simply, it’s the perfect and slightly tipsy way to end the trip.

If you’re wondering whether to spend 2 days in Chicago, it’s a no-brainer. The people are so friendly, and there’s many charming neighborhoods to explore. What’s more, the weather is superb come spring/summer, not to mention the delicious belt-busting food and drink. Once you’ve been, you’ll understand why it’s known as one of America’s best-loved cities.

Best boutique hotels in Chicago

I’ve 2 choices for travelers looking for boutique accommodation in Chicago. The first is the fabulous Thompson Chicago. This 4-star hotel is in the Gold Coast neighborhood, which is right near the Magnificent Mile. Its design is chic yet also homey, and if you’re lucky to get a lake-view room, you won’t be disappointed.

My second choice is The Robey in Wicker Park. It may not be downtown, but nonetheless, this Art Deco hotel’s a great place to stay in Chicago.

Disclosure: This post may contain affiliate links, which means I may receive a commission if you click a link and purchase something that I’ve recommended. Thank you for your support.

Like this post? Pin it!


48 hours in Chicago

2 days in Chicago

Perfect weekend in Chicago

Lisa R sitting in a wicker chair

Flashpack the right way

Sign up today for the latest content, and receive 3 free gifts directly to your inbox!

Nice to meet you fellow flashpacker!

Pin It on Pinterest

Share This