We have fond memories of visiting Chicago from back when we lived in Southern Ontario and always love to visit the windy city! Thankfully, you can fly to ORD – Chicago O’Hare on Alaska Airlines from YVR – Vancouver through SEA –Seattle-Tacoma airport which makes it a nice and easy place for a weekend getaway (pre COVID-19 of course). We have visited so many cities since we were last in Chicago and so we were unsure if we would up still enjoying this city as we have in the past but we did and found even more things to fall in love with! In this post, we share the 7 things we love the most about Chicago in the hopes of getting to visit again one day when we can travel again.

Alaska Airlines Welcome to Chicago Sign
Alaska Airlines Welcome to Chicago Sign

1) Walkability:

Most big cities are very walkable and for us, we love to set out on urban adventures from morning to evening and often end up walking 20 kms in a day. It is so easy to do that in Chicago and the scenery is pretty nice too. You can start from downtown and make your way to other neighborhoods pretty easily, and even take the scenic route by the river. If you’re up to it, you can even walk to/from the trendy Wicker Park area in about 1 hour each way pretty safely and get to see interesting buildings in smaller neighbourhoods. There are also many beautiful murals to admire in Chicago, including this one of Robin Williams.

We do not find it as easy as other cities to take the public transit here depending on where you are going and so we often rely on Uber/Lyft when we are here.

2) The Architecture:

Chicago’s skyline might not be as famous and dramatic as New York’s but it’s still pretty impressive. The buildings may not be as old as other cities because of the Great Chicago Fire in 1871 but this led to a construction boom, which attracted famous architects who transformed the city. We recommend admiring Chicago’s architecture on one of the architecture tours by boat if you are visiting between May 22 and October 12.  If you don’t have time for a boat tour to find out more about Chicago’s architecture, this post gives you information about 10 iconic buildings downtown.

3) The Food Scene:

Some come for the deep-dish pizza and others do not. We have been to Chicago about 8 times and have never had deep-dish pizza but that does not stop us from eating our way through Chicago. There is a great food scene here that is diverse culturally and even in style. You can have street food, fine dining and visit fancy food courts like the Time Out Market in a day. We do recommend checking out a hot dog stand like the Red Hot Ranch for a uniquely Chicago experience and remember to not ask for ketchup on your hot dog which is a faux pas.

Big Star Tacos is immensely popular but we recommend skipping it; each time we have tried to eat there, there was a 1 hour wait and the service was mediocre, even at the take-out window where we’ve walked out of.

4) Hanging out at Sawada Coffee and Green Street BBQ:

We also highly recommend checking our Sawada Coffee for “coffee until beer” due to its unique setting, awesome coffee, tasty donuts and shared space with Green Street Smoked Meats, a barbecue restaurant. The sides at Green Street are little pricey at but the bbq decent, they have craft beer on tap, and they have indoor and outdoor seating which makes it a fun place if you’re craving the Texas bbq scene. Perhaps our appreciation of Sawada and Green Street stem from the nostalgia of our weekend mileage runs to Austin Texas where we had coffee at The Buzz Mill and barbecue at Micklethwait Craft Meats after catching the red-eye. Yes, Sawada and Green Street are part of the food scene but they are so fun to hang out at that we felt they deserved to be in a category of their own.

5) The Hotels:

There are lots of hotels in Chicago which makes it easy to find deals to stay at really nice places. We have stayed at the airport in the last for cheap and took the train into the city and back but if you can, stay downtown. We like the Blackstone, Autograph Collection but recently it’s EMC2,  Autograph Collection that’s become our favorite. We would go as far as saying that it’s been the best city hotel we’ve stayed at in recent memory and would also add it to our top 10 list. EMC2 is close to everything but away from the noise too in downtown Chicago’s core.

EMC2 is such a treat for hotel design aficionados and was designed with the intent of hiding things in plain sight for your discovery. If you are sharing a room with someone, you might want to be well acquainted as the shower and vanity area are not very private but the shower itself encased in glass is unique and the shower head has good water pressure. We definitely noticed how high quality the bedding and linens were after staying at a Westin prior; you will sleep very well here and be comfortable in the plush robe provided.

We also appreciate Leo and Cleo, the hotel’s robots that deliver things to your room when you call the front desk.

Breakfast is included for Marriott Bonvoy Platinum and above and we do not agree with reviews that give the breakfast negative reviews; we found the service and the quality/quantity of the food to be quite high. We’ve tried the avocado toast, the breakfast sandwich, and the french toast and everything has been great. We also give them bonus points for making it very clear what is included and what is not compared to other hotels.

6) The Craft Beer Scene:

Like other cities, Chicago has a great and diverse craft beer scene that goes beyond Goose Island, which is not really craft beer anymore (sorry, not sorry). You probably won’t have time to visit all of them unless you are there for a long time and/or have a powerful thirst! Compared to other places, we do find beers expensive here; most are $7USD + tax + tip.

For a nice patio, check out Pilot Project. They have food here but it is more café style food.

Max at Pilot Brewing
Max at Pilot Brewing

For experimental but not too funky beers check out Off Color’s Mouse Trap. They have an outdoor space where you can stand because the inside gets really crowded and noisy.

Off Color Brewing Mouse Trap Location
Off Color Brewing Mouse Trap Location

For a pay by the ounce pour your own beer where you get to try from a selection of 40 beers from numerous breweries, District Brew Yards is the place to go.  For food, they have a bbq restaurant onsite and you can also purchase cans of beer to go.

District Brew Yards
District Brew Yards
Max pouring her own beer at District Brew Yards
Max pouring her own beer at District Brew Yards

Real beer geeks will appreciate Marz Community Brewing for its eclectic tasting room and beers. We had heard so many good things about Marz but we were slightly disappointed on our visit due to the selection of beers. We are just too hazed out these days to truly appreciate hazy and NE IPAs, which were prominently on the beer list.

Beers at Marz Community Brewing
Beers at Marz Community Brewing
Marz Community Brewing
Marz Community Brewing

7) The Airport: ORD – O’Hare International Airport:

Some people seem to hate ORD but we actually like it compared to other airports; it’s newer, cleaner, and has good food options, in addition to nice American Airlines Lounges.

American Airlines Admiral Lounge Chicago
American Airlines Admiral Lounge Chicago
Peloton Store at ORD
Peloton Store at ORD

Summary:

There is much more to Chicago than we list here but these are the things that we enjoyed the most and will keep us coming back (if and when we can visit again). For us, Chicago is a big city that does not feel as big as you would expect it but this could be due to the areas we explore. For us, it is just about walking as much as we can, admiring murals and buildings, eating good food, trying different beers, and relaxing in nice hotels; Chicago has it all!

Have you been to Chicago? If so, did you enjoy your visit? Any things to recommend that are not on our list?

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