From its impressive museums and galleries to its world-class theatres, historic sites and zoos there is something for every age and stage at the vibrant city of Chicago. We recently spent 3 days in the Windy City and were totally charmed by its rich culture, amazing culinary scene, and lively neighbourhoods.

Here is a Chicago travel guide with some of our recommended sightseeing, shopping and stay experiences for those who are planning a short trip to this lively city. 

WHAT TO DO:

Day 1

Start your Chicago tour by visiting the most popular gathering spot in the city, the 2.5-acre Millenium Park. It is known for its popular public art installations, free concerts, biggest outdoor festivals and proximity to the Loop. Take in a free outdoor show or admire the outdoor gallery displaying the work of great artists. 

If you are looking for more, make your way to the Art Institute of Chicago which is world-renowned for housing more than 300,000 artworks. From ancient Greek sculptures to Japanese prints, you can find a lot of contemporary treasures here.

Head to the Skydeck Observatory at the Willis Tower to get a bird’s eye view of Chicago. One of the most loved attractions, Willis Tower occupies two city blocks and stretches 1,454 feet high. You can walk out on the 1.5-inch glass and look at all the glassy skyscrapers spread out as far as the eye can see.

Day 2

Begin your second day by visiting one of the top landmarks in the city, Navy Pier. If you are holidaying with your kids, they would love to ride in the Ferris wheel, enjoy boat tours, play miniature golf or enjoy a leisurely walk with you. Don’t forget to try the divine stuffed Pizzas at Giordano’s Pizza outlet here that are extremely popular in the city.  

If you are a history buff, you could spend countless hours in the Field Museum. This humongous natural history museum is famous for hosting over 350,000 square feet of permanent exhibitions and thousands of artefacts. From ancient Egyptian mummies to towering dinosaur skeletons, there are too many things that will demand your attention here.

End your day by visiting the beautiful Buckingham Fountain regarded as Grant Park’s crowning glory and centrepiece. One of the largest of its kind, the fountain is famous for its jet streams that send water 150 feet in the air. At nights, you can even catch a light and water display show.

Day 3

For our last day, we rented a car and set off for the stunning small town of Winnetka. Did you know the award-winning movie ‘Home Alone’ was shot here? That’s right. The famous ‘home’ where Macaulay Culkin (aka Kevin) stays is located here. It felt surreal to visit the spacious mansion and relive a part of our childhood. 

On the way, we also visited Bahá’í House of Worship to connect with our inner self and revitalise ourselves. It was a truly spiritual experience and we are glad to tick this off our list. 

To make the most of the remaining day, we covered two more iconic attractions of the city – Chicago Riverwalk and 360 Chicago.

A stroll alongside the magnificent Chicago River was just what we needed to enjoy the city’s sights from a different angle. There are short cruises that you can hop on to admire the skyscrapers against the city line. 

If you want to conquer your fear of heights, visit 360 Chicago that offers unobtrusive views of the entire city below shimmering in lights. From 1,000 feet up in the air on the 94^th floor, the vistas from up here are truly a sight to behold in the evenings. Do click lots of pictures to take memories back home. 

WHERE TO EAT?

Indulge the foodie in you at these terrific joints:

• Three Arts Club Café

Situated inside the Restoration Hardware, this chic café is owned by one of the top restaurant groups in Chicago. Sprawled over five floors, it is huge, has the perfect ambience and serves lip-smacking dishes.

• Big Star

If you are all about outdoor seating while enjoying a lavish meal, check out Big Star which is well-known for its exquisite patio. You may have to wait to get a table, but trust us, it will be worth it. Don’t forget to try the tacos and margaritas while you are here.

• Lou Malnati’s

Your trip to Chicago is truly incomplete if you don’t try the deep dish with a side of the homemade ranch at Lou Malnati’s. This restaurant has every quality to become your go-to place in no time.

WHERE TO STAY:

The Windy City has no dearth of options when it comes to luxury and affordable hotels both. Here are some options you could consider:

• The Guesthouse Hotel

One of the gorgeous spaces that Chicago has to offer, The Guesthouse Hotel is perfect for those looking for a little “staycation.” It is situated in Andersonville just north of the city and offers spacious rooms at affordable prices. 

• Hotel Lincoln

If you want to have the best stay experience that’ll make your trip more memorable, check out this boutique hotel that screams elegance and grandeur. Nestled amidst the Lincoln Park neighbourhood there are lots of attractions nearby that are worth visiting. 

• The Drake

This iconic luxury hotel is known for welcoming notable guests like the late Princess Diana and Marilyn Monroe. It houses some of the top high-end boutiques and the noteworthy Palm Court.

WHERE TO SHOP?

Chicago is every shopaholic’s paradise. We have rounded up the best three places for you:

• Damen Avenue

From thrift shops and high-end boutiques to local stores and international chains, Damen Avenue has it all. The most popular strip extends from Bucktown to Wicker Park and must not be missed. You can even relax at pretty looking coffee and donut shops to refuel. 

• The Magnificent Mile

The Mag Mile, or officially known as the Michigan Avenue, stretches for a mile and is a favourite of locals and tourists alike. It plays host to several elite restaurants, historical buildings and enjoys access to the beach and riverfront. From stylish Forever21 stores to elegant Chanel, you can find almost everything on this street.

• The Shops on Armitage

Whether you want to shop for clothing, home goods or souvenirs to take back home, you can find all of it and more on the Lincoln Park street. Keep an eye out for its unique boutiques that will spoil you silly.  

USEFUL TRAVEL TIPS:

Here are some tips that can come handy on your trip to Chicago:

• Unfortunately, some of the most congested roads in the U.S. are in Chicago. So, if you are planning to take a taxi or even drive around, make sure you are prepared to face the traffic woes and have some time margin. 

• Don’t let the vista outside your window fool you into predicting the weather. Sunny days can be some of the coldest during winters here. It’s always good to have some layers with you for the ‘just in case.’ 

• If you are planning a long stay in the city, it makes sense to invest in a 72-hour unlimited CTA pass which only costs you $20. You’ll save a lot on single bus fares or Uber rides. 

• Buy the Chicago City Pass to get 50% off admission for some of the main attractions of the city, such as the Skydeck, 360 Chicago, the Shed Aquarium, the Field Museum and more.

Do hit us up if you wish to share your travel experiences with us. We would love to connect!

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