Skip to main content


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

On a shorter trip, particularly a long weekend,  being able to get to your destination relatively early in the day is a good way to make the most of your holiday time. With some planning and an early start, you can be in the mountains by 2:30 or 3 pm, and even squeeze a hike in! All other things being equal, this makes Banff fairly unique among major parks in the North American West.

On a shorter trip, particularly a long weekend,  being able to get to your destination relatively early in the day is a good way to make the most of your holiday time. With some planning and an early start, you can be in the mountains by 2:30 or 3 pm, and even squeeze a hike in! All other things being equal, this makes Banff fairly unique among major parks in the North American West.

There are basically three options for getting to Banff proper:

  • Public Transportation: From downtown Calgary you can take a $10 (CD) shuttle bus to Banff, but it only runs from May until early September.
  • Banff Airporter: This commercial shuttle runs multiple buses per day from YYC to several spots in Banff. It’s more expensive than the public option, but it’s more convenient. It’s around $50 / person in USD, but kids 6-17 are half price, and kids under 5 are free.
  • Car Rental: This is the option we chose. We rented a minivan through Turo so we could explore the Icefields Parkway and get to trailheads that were farther away. I would highly recommend this as you’ll be able to spend more of your time in the wild and less waiting on buses.
green trees of a chicago park in front of taller buildings

Where to Stay

Banff has a pretty broad range of lodging options, but because there just isn’t that much land to build on, they all tend to be fairly expensive. On the low end, there are several respectable hostels, including the HI Banff Alpine hostel and the Samesun Banff. Expect to pay between $40 and $70 / night for a bed in a shared room. At the high end there are the magnificent Fairmonts, one at Banff Springs and another up the highway at Lake Louise. They can run upwards of $600 / night for small rooms, but offer service and locations that you can’t find elsewhere.

We ended up checking out two places – the Delta Banff Lodge, which is a Marriott Bonvoy property, and the Mount Royal Hotel, a historic hotel operated by a niche hotel group called Pursuit. The Delta has since closed, likely for some updating, but I would recommend both. Neither hotel was particularly luxurious – the Delta offered bigger, quieter rooms and was a few minutes walk from Central Banff.

The Mount Royal was hipper and had a rooftop pool and bar, but had smaller rooms and more noise. It definitely had the better location and I would probably prefer it for a similar price. We mostly just used the hotels for crashing after long days out, and if that’s your plan as well, there are plenty of options.

Note: During peak season hotels book out very early consider reserving six or more months in advance. If the weather is cloudy or rainy, hotels will get cancelations, so you can snag a room at the last minute for quite a bit less money than you could if booking ahead. But if the weather is glorious, you might not get your preferred room (or any room).

marina city towers in chicago and river bridges raised up

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)

Related Reads

Leave a Reply