Catch Flights, Not the Cold to the Windy City, Chicago

When you think of the largest cities in the United States of America, what comes to mind? If you thought of either New York City, Los Angeles or Chicago, you named one of the top 3 most populated areas of the U.S. These cities are on the top of everyone’s travel list. Each location has its own character and major iconic landmarks that everyone is aware of, as well as an abundance of things to see and do. Each city has its own characteristics and unique food scene.


Before You Start Planning

Chicago experiences all four seasons, so be mindful on which type of weather you are most comfortable with. For me, great weather is when it is nice and sunny with temperatures in the 70s. However, I visited Chicago in February, which was 7 degrees Fahrenheit and snowing, the polar opposite of what I am used to.

Caution: Falling Ice

This made my experience a little tougher to enjoy. As a Californian, I have never experienced cold like that before and I know it can get worse. Make sure to check the weather before planning your trip. You don’t want to be caught in the Snowpocalypse like I did.

How Many Days is Recommended?


All of the tourist items in Chicago are located in the Chicago Loop and can be finished within a day. The other days that you spend there can be used by being immersed in the culture and dining experience. Depending on how many restaurants you have on your list, I would say 2-4 days would be enough to experience Chicago.



There is public transit such as the trains called the ‘L’ and buses, which you can use to maneuver around the city. Having a car would be helpful but not necessary, it could also be a hassle due to parking. There are rideshare services such as Lyft and Uber, and also taxis available to take you to places outside of the city center if you do not rent a car.

Hotel Accommodations

For accommodations, there are many choices depending on what you are most comfortable with and where you want to stay. Hotels, Airbnbs, and hostels are spread throughout the city and can accommodate all budget types. I would suggest staying in the city near all of the food and entertainment so you can walk rather than drive or take a taxi everywhere.

On my trip, I purchased a packaged vacation for Southwest Airlines and the DoubleTree hotel located in downtown, central to everything.

Eat the Iconic Chicago Style Food: Deep Dish Pizza and Chicago-Style Hot Dog

First things first, food! The two most popular Chicago style foods are the deep dish pizza and Chicago-style hot dog. They are different than the average pizza and hot dog you have anywhere else.

You can’t go to Chicago without having a slice of a deep dish pizza. It is jam packed with cheese, not suitable for the lactose intolerant. The experience in it of itself is a food  awakening. The venues are dimly lit with tables seated close together, making it an intimate dining experience. The deep dish pizza is a process to make and requires time for preparation, thus it is necessary to allocate enough time to assemble. Pizza in Chicago is a table dining experience rather than a grab-and-go like other pizza hubs across the nation.

The two main competitors of the Deep Dish pizza are Lou Malnati’s and Giordano’s. Lou Malnati’s, not to be mistaken as Illuminati, is only available throughout Chicago, whereas Giordano’s has expanded across the nation. It is often argued that Lou Malnati’s has a buttery crust whereas Giordano’s is soggy. Try both and decide for yourself which one you prefer!

The typical hot dog consists of a bun, hot dog link/sausage, ketchup, and mustard. The Chicago-style hot dog, however, comes with an all-beef Frank encased in a poppy seed bun with tomatoes, pickles, sport peppers, sweet relish, yellow mustard, and celery salt. I can eat these all day!

The Chicago-Style Hot Dog is available throughout the entire city, great for lunch, dinner or a quick snack. Some places you could get your hands on these delicious dogs are Superdawg, Gean & Jude, and Portillo’s which can be found throughout the country. The hot dog chain, Portillo’s has a ridiculous Chocolate Cake Shake that is for the fatties at heart, with a secret, unexpected ingredient… mayonnaise! There is an abundance of hot dog stands and shops that you can even do a Chicago-style hot dog crawl to deem which hot dog trumps the rest.

Don’t leave Chicago without trying these food items!

Shuffle and Fist Pump to House Music

“I must of went to house heaven… because nothing is that divine” – Divine by Jamie Antonelli

Chicago House Music

The birth of Chicago House, or simplified to House music, was right in the city of Chicago after the disco era. This gave rise to the nightlife and changed the sounds of dance music.

Nightlife in Chicago is similar to the nightlife in large cities like Los Angeles. There are clubs throughout the city where they let you in free of charge, all you need is their secret “password”. These are similar to being on the “guest list” in other parts of the country.

During my time in Chicago, I went to The Mid, which has the atmosphere of a warehouse party and Sound Bar. Unfortunately, I got wind that The Mid closed its doors in 2019. There are clubs and bars that still have their doors opened such as Stereo Nightclub.  

Chicago Loop

South of the Chicago River, the Chicago Loop is where most tourists flock.

Millennium Park


With Chicago not having many places to sightsee for tourists, Millennium Park has been the center of tourist attractions. There are several art displays and statues you can stare at and try to make sense of what it is supposed to be. 

Cloud Gate

Cloud Gate

Other than the Deep Dish Pizza, Chicago’s most iconic landmark, referred to as “The Bean”, is Cloud Gate. It is an art sculpture that turned into the most visited spot in the city. When you look in it or take a picture of it, it reflects the beautiful Chicago skyline of tall buildings. Go under it and take a look at your warped reflections.

Ice Skating 


During the winter season, a section of the park is turned into an ice skate rink. You can truly get into the spirit of the season by gliding around in the natural cold weather. Admission is free and open to the public. If you don’t have any ice skates, you can rent them on the spot for $13-15.

Crown Fountain


A very silly fountain located in the vicinity of Millennium Park. It is an art display consisting of LED screens with the illusion of different people spewing water out of their mouths.

Buckingham Fountain

“Love and marriage, love and marriage. Go together like a horse and carriage.” Does this theme song sound familiar? It should! But for those unfamiliar, it is from the television show, Married with Children.

Not to be confused with the Buckingham Palace, Buckingham Fountain is one of the largest fountains in the world and has a cameo in the Married with Children title sequence. Just a stone’s throw away from Millenium Park (about a half mile walk), is another great opportunity to take another one of Chicago’s treasured architecture.

Willis Tower (Skydeck Chicago)


Formerly known as the Sears Tower. If you ask any of the locals, they will point you to visit this. The Skydeck is most famous for the “The Ledge” where you can take photos of yourself sitting or standing on top of a glass that overlooks the city. 


To get here, you must buy admission tickets to go up the elevator that takes you to the 103rd floor. Once you get there, it is free to sit on top of the glass and take a photo. Worth a visit since the views are spectacular!

Navy Pier

Similar to many piers across the United States, Navy Pier is your typical pier with your average Ferris wheels, rides, and entertainment. However, it is on a much larger scale than Santa Monica Pier and the like. The Navy Pier also holds restaurants and the movie theaters. It is also large enough to host concerts and events.

Above and Beyond at Navy Pier

During my time in Chicago, I was able to purchase last minute tickets to see Above and Beyond, well-known Trance duo.

Chicago River


Chicago is divided into 2 parts, North and South. The Chicago River is the body of water that divides the city. During the winter, the river is frozen and walking by it will make the wind feel like ice daggers.

Magnificent Mile

For all of your shopping and fashion needs is the Magnificent Mile, just north of the Chicago River.

John Hancock Tower (360 Chicago)

In lieu of the Willis Tower, you can view the city from the observation deck of the John Hancock Tower called 360Chicago. It is a shorter wait time and cheaper admission prices. For an extra cost, you can experience Chicago with a thrilling “ride”, TILT. This experience will tilt your body outward so you are at a 30 degree lean above the city. The only thing preventing you from falling is a glass window and the metal bars you hang onto on the side.

There is also a way around paying for the observation deck if you just go to the Signature Lounge on the 96th floor to grab a drink or dinner. Please be advised that the prices are a bit pricier due to the location and the cost of the view.

Chicago Water Tower


Located in the Magnificent Mile neighborhood, the Chicago Water Tower is an interesting stop. This historical architecture is best viewed in the day time to capture its style and elegance. On the outside, it will probably take you a good 5 minutes to look at it and take a picture of. It is no longer used as an actual water tower but rather as a gallery to hold the photographs of the Water Tower.

Joe’s Seafood, Prime Steak & Stone Crab 

Located in Magnificent Mile, Joe’s Seafood is one of the highest rated restaurants, where you can get surf and turf dinners. As stated in their name, they are known for their stone crabs. It is an upscale, fancy restaurant so don’t come in wearing shorts and sandals.

My experience was that it was nothing different from other steakhouses, it is similar to Ruth’s Chris and the like. It wasn’t until afterward that I realized that Joe’s Seafood has restaurants located in Las Vegas, and Washington D.C. as well. If you frequent Las Vegas and Washington D.C., I would save Joe’s Seafood for those cities and explore another restaurant only available in Chicago.

Devon Seafood Grill

Upscale seafood restaurant with an amazing happy hour! The oysters are only $1 and the fresh appetizers such as calamari are at very reasonable prices.


River North

The Purple Pig 

All pig dishes. All pig parts.

If you love eating pig, this is your place! If you don’t, like me, you will have trouble finding things to eat. They have all of the pig parts you can think of: pig ear, pig head, pig liver, etc. This is a tapas style restaurant where you should order multiple dishes and share them amongst your party.

We didn’t have any reservations before entering but was able to be accommodated. But as always, if possible, make reservations beforehand!


When you dim the lights to restaurants, that’s when you know they are fancy right? Bavette’s has the dimly lit, fancy restaurant feel. Not only that, the atmosphere and ambiance take you back to the old school, Chicago mob-life days. Bavette’s is designed as if you are in a speakeasy during the Prohibition era.

It is known as a steakhouse with all of its usual fixings such as steak, seafood and crab cakes paired with aesthetic cocktails you can enjoy. Bavette’s is one of the highest rated restaurants in Chicago and has recently opened another location in Las Vegas.


An Italian marketplace where you can find Italian food and drinks. Eataly has your favorite Italian dishes such as pizza and pasta. And yes, there’s gelato! You can find a majority of your favorite Italian products here, whether you want to eat it in house or take it home to cook yourself. There are several locations available throughout the nation as well as worldwide. Nestled in large cities, Chicago is 1 of 5 locations in the U.S.

Five Faces Ice Cream Shop

To my disappointment, this place is not an actual ice cream shop. Five Faces Ice Cream Shop made up my disappointment by offering some of the best late night snacks. You can get a Chicago-style hot dog or some chili to help warm up the cold weather. The employees there are friendly and will joke around with you despite having to work graveyard shifts.

Fulton Market District


The Fulton Market District is another gentrification story added to the history of the city of Chicago. When you are here, it is evident of what it used to be, meatpacking, industrial district. You will get a sense of the old and the new coming together to make it a more modern area filled with trendy restaurants such as Girl & The Goat, Little Goat Diner, Duck Duck Goat, and Au Cheval. It is rumored that the double cheeseburger at Au Cheval is something to rave about. But let me know if you think it is overhyped. As an added bonus, check out the Mcdonald’s new headquarters in this area!

The Publican


Grab breakfast or brunch at The Publican. It is one of the modern restaurants located in the Fulton Market District with community style seating — meaning one very long table with seats facing each other. I had brunch here and personally it felt a little overpriced for what you get and our toast was burnt.

Make sure to grab reservations if you can as it gets extremely crowded during the mornings.

United Center  

Home of the Chicago Bulls and the Chicago Blackhawks. Perfect for if you are a basketball or hockey fan. If there isn’t a game happening, you can still visit the United Center and pose with the statue of the apparent “best basketball player in history”, Michael Jordan. Also, you can see other statues of legends in hockey.

The Fun Doesn’t Stop Here

(Other Recommendations):

  • Dine at the Michelin-starred Alinea, a most well-known restaurant and sought after seat in Chicago


  • Grab a late night snack at Jim’s Original, great hot dogs for when you have the drunchies. Not a Chicago-style hot dog spot, but a hot dog nonetheless.
    Bonus: All sandwiches come with fries!
  • Fan of the show “Shameless”? The Gallagher’s house is located in Lawndale, Chicago but it is in the bad area of town so if you truly need to visit, take your picture and GO! Do not linger around.


  • Get happy hour oysters at Shaw’s Crab House


Get Weird in Portland, Oregon

You can feel the Portland vibe as soon as you take a look around you. Everyone has their own ways of presenting themselves and their own way of doing things. When I landed in PDX and walked out of the airport, I inhaled my first breath of fresh air. With Portland having a million trees, it may be one of the freshest breath of air you’ve ever had, if you’re coming from smog city, Los Angeles. Next, you’ll soon notice that people here are not caught up to the newest fashion trends, or have any sense of fashion at all. The way to best describe it would probably be “Hot Topic” fashion.

Places to See and Do

Admire Multnomah Falls


Multnomah Falls is the tallest waterfall in Oregon and the most popular natural attraction. You can view the waterfall from the parking lot or you can hike up to the bridge and view it from the top down. This place is CROWDED and packed with tourists, you might have trouble finding parking. Multnomah Falls is about 40 minutes from downtown so you would need a car to get there.

James Woodhill Park at Rocky Butte


Opened from 5 AM to midnight, this is a nice romantic place to view the city lights below.

Go Shopping at the Nike Factory Outlet

I came to Portland with the impression that the outlet stores will have major discounts but when I dropped by here, I was pretty disappointed. The prices were the same as any other Nike Outlet stores I’ve been to, the only positive thing is that there is no sales tax!

Ride the Brewcycle


Portland, Oregon has the largest brewery scene of any city in the world. With so many breweries and microbreweries, it is difficult to choose which ones you want to go to. I went on the Brewcycle, which is a fun way to tour the breweries and have means of transportation from place to place without the worry of driving. We went the Old Town route and had a great time, our guide was more than pleasant. All of the breweries we went to were fantastic. My favorite was Fat Head‘s Brewery where I got to try the Honey Blueberry Ale.

Go Brewery Hopping


If you love beer as much as I do, Portland would be beer heaven. One of the more popular breweries is Deschutes Brewery. I remember picking up a 6-pack at my local Bevmo that was brewed by Deschutes Brewery, so it was cool to actually be visiting it. In Pearl District, there is an abundance of breweries that you should check out. A couple of them are Hopworks Urban Brewery, Rogue Distillery and Public House, Cascade Brewing Barrel House, and Upright Brewing just to name a few. There are breweries spread out all over Portland, it’s just a matter of which district you would like to visit and brewery hop in.

Stop by Vista House at Crown Point


After your hike, make a stop to Vista House to catch a beautiful view of the Columbia River Gorge. There are restrooms here!

Hike to Wanchella Falls

If you’re anything like me, low risk, high reward hikes are my sort of thing. I will not hike 10 miles just to see a waterfall that I can hike 1 mile to see elsewhere. As you can guess, Wanchella falls is a short and easy hike (about 22 minutes) with a waterfall awaiting at the end. Best of all, nobody is around to bother you!

Forest Park

As the name should already describe it, Forest Park is a very LARGE and GREEN park filled with trees. Portland has a reputation for having trees all over and this park is no different from that. There is an abundance of hiking trails you can do but I thought the most interesting ones are Ridge Trail, Witch’s Castle and Wildwood Trail (which should be hiked in different parts).

Smell the Roses at the International Rose Test Garden


Portland is full of nature, it’s no surprise here. Aside from the trees and the waterfalls that Portland has to offer, Portland also contains a lot of roses. In fact, one of the nicknames is the “City of Roses”. Close to Forest Park, this garden is full of rose bushes you can walk around during the bloom months. It is free to the public and best of all, free admission. Worth checking out! I was amazed by how many roses and different varieties there are.What a site to see! After all, you should stop and smell the roses.

Lan Su Chinese Garden and Portland Japanese Garden

It doesn’t just stop at International Rose Test Garden for all of the gardens in Portland. No, there is a handful of them but they are not free admission. Lan Su Chinese Garden and Portland Japanese Garden are both near the International Rose Test Garden and cost $10 and $15 per adult respectively. If you are a student, there is a reduced student admission price.

Ground Kontrol Classic Arcade

School your friends in video games or play retro arcade games. Reminisce your days of growing up with pinball machines and throwback 70s-90s games. Do what you were not able to do as a child and knock back a few drinks while challenging your friends, as Ground Kontrol is a barcade.

Strip Clubs

Alongside breweries, Portland is known to have a crazy amount of strip clubs, the most per capita in the great country of the U.S. of A. It is arguably said that Portland even has the best strip clubs in America. There is literally a strip club for any types of people. Next door to Voodoo Donuts, I stumbled into Kit Kat Club. It wasn’t like anything that you normally see in Las Vegas or the like. They actually have a lot of talent and strength. It was more like a show than a sleazy strip club with perverted men. There are some strip clubs that you can have a steak dinner inside, such as Acropolis Club.

Places to Eat

Portland Oregon


The Waffle Window

Looking for a quick breakfast? Do you like waffles? Head over to The Waffle Window where you can choose savory or sweet options. Daily specials are also available aside from their main menu. There is indoor seating available or you can take your waffles to go. Opens at 8 AM daily.

Pine State Biscuits

If you don’t like waffles, maybe biscuits are more your thing. Pine State Biscuit is one of the popular breakfast joints in Portland, so expect to be waiting in a long line. They are serving up fluffy biscuits and gravy at 7 AM daily.

Screen Door

Very, very busy restaurant! I had this place on my itinerary but we were unable to wait for a table here. Word on the street is, this place has some BOMB chicken and waffles!

Blue Star Donuts

If you eat donuts for breakfast, head on over to Blue Star Donuts to get artisan flavored donuts. Aside from the famous Voodoo Donuts, Blue Star Donuts is a Portland native that has made its way to Los Angeles and has multiple locations. Blueberry Bourbon Basil is one of the most interesting and popular donuts they have. If that doesn’t sound appetizing to you, there is a good variety for you to choose from. Be expected to pay about $3 a donut though. I went a bit crazy the first time I came here and thought the donuts were just “okay”. But I think I chose the wrong flavors.

Tasty n Sons

Tasty n Sons, another cool and hip restaurant to get your day started. They also are serving up dinner as well, since they are opened for over 12 hours of the day. The Burmese Red Pork Stew seems to be a popular pick amongst patrons.

Lunch / Dinner

Pok Pok

If you haven’t heard of Pok Pok before, you haven’t done your research into the food scene of Portland. This Thai cuisine establishment was made popular through the fish sauce wings being “the best wings of Portland”. I had lunch here with my friends when I visited and we had quite a wait. Truthfully, we thought the only decent thing was the wings and even that, we thought was a bit too salty. Maybe we had it on an off day, maybe not but we weren’t too crazy for the food.

Pok Pok, another Portland native that tried to venture out to Los Angeles, unfortunately, did not translate well to the diners of Los Angeles and eventually closed.

Nong’s Food Cart

Food carts are all the rage in Portland. One of the more popular food carts is Nong’s Khao Man Gai, which is known for its Hainan chicken. There are multiple locations so it’s a greater chance that you will be nearby one to have for lunch. Also, check out neighboring food carts to get the food tasting tour experience.


Similar to the previous recommendation of Nong’s food cart, Cartlandia (8145 SE 82nd St.) is a place where food trucks meet. There is also a beer garden where you can sit and have a brew with the food you purchased. One of the interesting things there is the lobster mac and cheeseburger from Melt it! Aside from Cartlandia, there are a LOT of food carts to choose from in Portland. Check out this link for more.

Por Que No? Taqueria

I’m not sure how Mexican food tastes in Portland, but I would give Por Que No? Taqueria a try if I was craving some tacos. All taquerias should serve agua frescas and when they do, it’s a plus in my book. In addition to that, Por Que No? is serving up some tasty margaritas! There is also happy hour here from 3 – 6PM daily!

Bollywood Theater

Bollywood Theater first sounds like somewhere I can watch some Bollywood, but no it’s an Indian restaurant serving up Portland’s Indian burrito called “Paneer cheese Kati roll”. THAT looks amazing, along with their other dishes.

Podnah’s Pit BBQ

Get your Frito pie here at Podnah’s Pit BBQ! If you’ve never had real BBQ before, Podnah’s would be a good beginner but I was no rookie to BBQ so I thought Podnah’s is, unfortunately, skippable. My friends and I were running around town finding a place to sit down and eat dinner as soon as possible. Podnah’s was the only place we didn’t have to wait 1 hour to be seated. The service was great and the Frito pie was alright.



Great place to grab a burger and a beer. TILT has a fun mechanic theme with shop towels instead of paper napkins to save trees. Don’t leave without grabbing a slice of their delicious pies.

Little Big Burger

Little Big Burger is a chain burger joint with multiple locations in Portland. The burgers are a small size, about 2-3 bites worth, but they are BIG in flavor. In order to be full, I think I would need to eat 3 burgers worth. Good to try, pretty tasty but can get expensive. Little Big Burger reminds me of In-N-Out due to its very simple menu and similar pricing. However, one thing different is the cheese is pepper jack instead of American cheese. If I had to pick though, I’d choose In-N-Out burgers any day. The truffle fries, on the other hand, beats In-N-Out fries. Be sure to give Little Big Burger a try and remember to get the truffle fries with catsup and fry sauce.

Cruzroom Taco Lab

Infused vodka flights?! COUNT ME IN! Happy hour is available every day of the week except Sundays.


Get your sandwich fix here! Lardo is a solid place in Portland for you to enjoy your choice of meat between two slices of bread. Be sure to pair it with some dirty fries, as they are a hit here at Lardo.

Toro Bravo

If tacos aren’t your thing, maybe some Spanish cuisine is? If so, check out Toro Bravo for dinner as it is a tapas bar! Small place so seating is extremely limited. My friends and I tried to get a seat here for dinner but the wait was extremely long and we were extremely hungry so we decided Toro Bravo would maybe be best for another time.

Apizza Scholls

I have never met anyone that hated pizza, nor would I care to. At Apizza Scholls, you can build your own pizza or select one of the house pies they created. It is a New York style pizza joint with the best ingredients to make your pie a delicious one. So what are you waiting for? Head on over to share a pie with your friends.


Salt & Straw Ice Cream


Salt & Straw has been so widely popular that it began to open locations in Los Angeles. Nonetheless, still, a good place to try different flavors of ice cream.

Fifty Licks

If you want to go a different route for ice cream besides Salt & Straw, try Fifty Licks. This place has more of the original flavors as well as different, interesting flavors such as Lavender Mint Chip and Thai Rice!

Happy Hour

In my opinion, Portland lacks a nightlife unless you are into Strip Clubs, so your best bet to having a night out is just hanging out at the bars. Perhaps catch some late night happy hour specials while you’re at it. Here are some happy hours I’ve noted while planning my itinerary:

The Observatory

Happy hour is available here from 10 to close.

Slow Bar

Happy Hour is available here from 12 midnight to 2:30 AM

Victory Bar

Happy hour is available here from 5 – 6 PM (daily) as well as 11 PM-Midnight (Tu-Sat)

Mother’s Bistro and Bar

212 SW Stark St.

Happy Hour is available from 3 – 7 PM (Tu – Fri) with $3.95 plates when you purchase any beverage.

If you have any questions or believe that I missed something major, please leave it in the comments below!