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Chicago is a beautiful city, filled with a rich and exciting history as the third largest city in the nation. The shores of Lake Michigan have attracted people from all over the world. Because it is made up of many smaller neighborhoods, the best advice for a traveler would be to get on any “L” line, ride it until you see an area that interests you, and then get off to explore. However, if you need a more structured itinerary, there are many exciting attractions that can be explored in just three days.

Chicago is one of the easiest cities to get to. Its two major airports are hubs. So even if you’re coming from a smaller metro area, you would have had a layover in Chicago anyway. That makes it one of the cheapest cities to fly into.

The city is also a major rail and interstate hub thanks to its central location in the middle of the country. Chicago is only a 2-hour drive south of Milwaukee and a 3-hour drive north of Indianapolis. Even Detroit and St. Louis are within a morning’s drive, giving you ample time for afternoon and early evening exploration.


Chicago, IL, USA. 


Eating, Shopping, Art, Music


2-3 days

Getting There

Chicago is lucky enough to be one of the most well-connected cities in the country. It boasts two major airports that service the metro area. The largest is O’Hare International Airport (ORD). In fact, it is the most-connected airport in the country, with 278 unique destinations travelers can fly to. A rideshare or taxi into downtown should take around 30 minutes, depending on traffic, and will be around $35. Alternatively, you can take the Chicago “L” Blue Line directly from the station at O’Hare to downtown. The ride takes about an hour and costs $5.

Midway International Airport is the 2nd major airport for the Chicago metro area. It is a hub for Southwest Airlines, which makes up 93% of the flights at Midway (though they do also fly to O’Hare). Midway tends to focus more on low-cost carriers like Southwest and Frontier, though they do have a small number of Delta flights. Like O’Hare, Midway is about a 30-minute car ride from downtown. A rideshare trip should cost around $35. For those opting to take public transportation, the Chicago “L” Orange Line will get you downtown in about 50 minutes for a cost of $2.50.

Those who are driving will find Chicago incredibly easy to get to. The city’s midwest position put it at the crossroads of numerous major interstates, namely I-90 that goes from Seattle to Boston. Milwaukee is only about 2 hours north via I-94. Indianapolis is just 3 hours southeast on I-65. Even St. Louis and Detroit are only 4.5 hours away—an easy trip for a weekend getaway.



Where to Stay

As a major U.S. city, Chicago has everything ranging from swanky Four Seasons rooms that cost thousands of dollars to inexpensive shared-room hostels. If you’re looking for something locally unique, check out the Publishing House BNB nestled in the heart of the city’s historic West Loop neighborhood. This boutique bed and breakfast is a converted 19th-century publishing house blending modern comforts with a touch of vintage elegance. From the moment you step inside, you’re greeted by a warm and inviting atmosphere, with shelves adorned with a curated collection of books and cozy reading nooks scattered throughout. The staff are more than happy to recommend hidden gems to explore throughout the city. As the sun sets, the rooftop terrace offers breathtaking views of the iconic Chicago skyline. Room prices range from $220-$380, depending on size.


Friday Afternoon

One of the first things to do after arriving in Chicago is to explore the Loop. Many of Chicago’s most iconic landmarks are located in and around downtown. Walk around and take a look at some of the famous buildings, such as the Willis Tower and the Chicago Theatre. While in the area, stroll across Michigan Avenue into Grant Park. Snap a picture of Buckingham Fountain. From the park, you will also be able to see how beautiful Lake Michigan is in the afternoon sun.

Buckingham Fountain

Just at the edge of Grant Park is the Art Institute of Chicago. You won’t be able to see everything in one visit, but you will be able to get a great idea of why Trip Advisor always keeps the Art Institute somewhere in the top 5 of its “Best Museums in the World” list. See such famous works as Georges-Pierre Seurat’s A Sunday Afternoon on the Island of La Grande Jatte and Pablo Picasso’s The Old Guitarist. And if you can make it into town on Thursday, you can take advantage of the free admission every Thursday night between 5:00 and 8:00 p.m.

Friday Evening

There are many hotspots to spend a fun Friday night in the Windy City, but it is hard to find one with as much charm as Kingston Mines. In one of the most famous blues nightclubs in the world, you will be able to let loose and enjoy live musicians who are masters of their craft. The club has received many honors over the years, such as in 2014 when it was awarded the “Keeping the Blues Alive Award” by the Blues Foundation.

Saturday Morning

Spend your morning exploring one of Chicago’s smartest and chicest neighborhoods, Wicker Park. Be sure to check out Myopic Books, one of the city’s oldest bookstores, which claims to have over 800,000 volumes on its shelves. Also, while you are in the neighborhood, grab a gourmet doughnut at Firecakes Donuts.

maple glazed pineapple and bacon donuts - Firecakes - Baconfest 2013.jpg

Saturday Afternoon

In the afternoon, head over to Montrose Beach at Lake Michigan. From there, you will have excellent views of both the city skyline and the extraordinarily blue water. Enjoy an afternoon in the sun or walk along the shore with the wind in your hair.

Saturday Evening

Catch a movie at Music Box Theatre, a movie house that has been in Chicago since 1929. For the better part of a century, Music Box has provided the city with treasures in independent and foreign cinema. On the weekends, there is a live organist who performs before each screening.

Sunday Morning

If you are coming between May and October, there is no better place to spend your morning than at the Green City Market‘s outdoor farmers’ market in Lincoln Park. Whether it is naturally-grown produce or hand-crafted jewelry, you are bound to find something you love here.

Strawberries Seasons First KCI08279

Sunday Afternoon

Right next to the farmers’ market, make sure you check out Lincoln Park Zoo. This is a must-see, especially if you are traveling with children. Oh, and did I mention that admission is free? Come and see a wide variety of exotic animals from all over the world.

Sunday Evening

If you can stay into the evening before heading home, there is no better place in town to spend a Sunday night than at the Green Mill, which hosts a weekly Poetry Night. Not only is this the legendary jazz club where Al Capone spent his free time, it claims to be the place where slam poetry was first conceived. Whether or not you are a fan of spoken word, the moderators get the audience involved and ensure that everyone in the house is entertained.

Green Mill Lounge (Gangsta's Paradise)

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