Three days in one of America’s most iconic cities

The steel and glass of downtown Chicago | **Sean Pavone / Shutterstock**

Even if you’ve never visited Chicago before, it will likely feel familiar. Whether you grew up watching Home Alone or Ferris Bueller, caught a Cubs / Blackhawks / Bears game on TV, or seen the river dyed green each St. Patrick’s Day on the news, there’s an iconic air to the USA’s Second City.

There’s an awful lot to explore too and, if we’re being honest, it’s almost impossible to see it all in a weekend. However, we’ve created a fast-paced whistle-stop tour of Chicago with this weekend itinerary, so you can see the must-sees and do the must-dos even if you need to be back to reality first thing on Monday morning. So let’s dive in and spend a weekend in the Windy City!

Planning and Preparing

You’ll likely fly into Chicago for a weekend trip | **MKPhoto12 / Shutterstock**

Chicago works best when you focus on exploring the city and sort of park the logistics. No matter where you want to go, or where you want to stay, getting around is a breeze. There is extensive mass transit, including the famous L Train, a huge bus network, plus downtown is surprisingly walkable.

The main things to really consider are how you’ll get from O’Hare (the main airport) or Midway (the secondary airport) to your hotel if you’re flying in, and which attraction you want to focus on. With tickets selling out fast year-round, especially on weekends, you want to be arriving with a time slot or ticket in hand, rather than. wasting your Saturday or Sunday morning waiting in line.

Solve the transit problem with either a pre-arranged transfer, or by grabbing a Ventra unlimited pass, meaning you can use the entire city’s public transport all weekend for $15, a true bargain.

Other than that, you may want to pick a restaurant or two, but you’ll probably find you can easily get lost in casual dining in a city that’s more about pizza than pretentiousness.

What to Pack

You’ll be walking, a lot, regardless of the season, so sturdy and comfortable training shoes or boots are item number one in the suitcase or carry on. Summers get hot and winters get mega cold, but Lake Michigan can dump a cold front on you at any point.

A thick, wind and waterproof jacket, hats, gloves and anything else warm is essential September-March, and a layer or two doesn’t hurt in summer. An umbrella won’t go amiss at anytime.

Day One - Friday Evening

Chicago on a Friday night is energetic and fast-paced | **Sean Pavone / Shutterstock**

Once you’ve navigated your transfer from the airport or dragged your luggage across the concourse at Union Station, it’s time to check in. And why not make your hotel part of the experience?

The brand-new Riu Plaza Chicago towers above Michigan Avenue, one of the city’s most famous streets, with a huge glass-floored balcony opening your Instagram spamming for the weekend with some unbelievable views of the city, at no extra cost.

If you’re after something a little more refined, then try Pendry Chicago, inside the old Carbide & Carbon Building, which oozes golden age, art deco class.

After you’ve unpacked and freshened up, it’s time to eat. Chicago is of course the home of deep pan pizza, and Great Lakes up in Andersonville (hop on the L train with your Ventra) is the place to get it. Expect a wait, which is well worth it.

If you’ve got the energy, then Red Line is back Kumiko, an award-winning dining bar with cocktails, snacks and views. Don’t overdo it, as tomorrow is a busy one.

Day Two – Saturday

You have to include a trip to the Bean in your Chicago itinerary | **James Kirkikis / Shutterstock**

Shake yourself awake, grab a shower and a coffee and head over to the East Ukrainian Village, and more precisely Kasama. This Michelin-starred Filipino restaurant just happens to also house one of Chicago’s best bakeries, with outstanding pastries and breakfast treats. The pork-belly adobo breakfast sandwich is the top seller, and has won awards.

After you’ve refuled, head to a Chicago icon two stops away – The Bean in Millennium Park. Get your obligatory selfie in the reflective surface and get outta there before the crowds descend.

Spend more time in the Art Institute of Chicago across the concrete, which has way more impressive pieces, with some amazing river views to boot.

If you’re not still full from breakfast then stroll onward to Monteverde (the gelato is superb). Then head up to the river dock and pull out your phone to flash your pre-booked Chicago Architecture Center cruise tickets. Over 90 minutes, you’ll sail past the majority of the city’s essential buildings, from the ornate Wrigley Building to the less beloved Trump Tower. Camera at the ready.

If you’re in the mood for a splurge, then make sure you’re booked Oriole well in advance for dinner. Here, you’ll run through a tasting menu that includes king crab, beef garum and wagyu. Three hours will feel like 30 minutes.

Cap off your Saturday with a trip up to 360 Chicago, which stays open until 11pm. It' may be slightly less busy and the views across the city at night can be quite something. Try the TILT platform for a quick thrill before bed, unless you overdid it at dinner.

Day Three – Sunday

The Ledge allows you to hang over the edge of the Willis Tower – safely | **Salvador Maniquiz / Shutterstock**

Enjoy an easy start before meandering over to Lula Cafe for breakfast, namely the fluffy omelette with onion relish. That’s just part of the reason you’re over this way, however, with the next door cafe hosting a weekly seasonal farmer’s market, so enjoy a good browse.

If the Cubs or Bears are in town, then you may be lucky enough to catch a Sunday afternoon fixture. Again, advance tickets are essential and remember not to go too overboard on souvenir giant foam fingers or bats if you’ve got limited carry on allowance.

If sports aren’t for you, then say goodbye to Chicago from the Willis Tower’s Skydeck. Raise your heart rate at the Ledge, where an inch-and-a-half of glass is the only seperating you and a 1,353 foot drop to the street below.

If you have time, grab lunch or dinner at Lem’s Bar-B-Q, where the rib tips will keep you going for the ride / flight / train home.

With your weekend in Chicago complete, it’s time to plan a longer trip next time as you head home!