Traveling to Chicago for a weekend, and you need some ideas on where to stay, what to eat and what to do? As a three-year resident of Chicago I know the essentials of Chicago and what should be avoided. Chicago is an underrated city and tourists are surprised with how appealing this city actually is, I know I was. But first you need a local to tell you some of the hot-spots or you may end up thinking Navy Pier was the best part of your trip.
Getting into Chicago
Most travelers will fly into Chicago and in fact O’Hare and Midway are some of the busiest airports in the world. From the most populous cities in the US and Canada, Chicago is within a 4 hour direct flight, making it convenient. From O’Hare you could take a taxi (no Uber from the airport) costing you $40 – $50, the CTA L Blue Line which is $2.25, or hire a private shuttle for as low as $14 if you’re traveling with a bunch of friends.
Taking a taxi is expensive but if you’re heading to Michigan Ave with luggage it may be the best option. The CTA Blue Line is convenient, cheap and heads directly downtown where you can transfer to your hotel by walking or with a bus.
From Midway you can do all the three like O’Hare, a taxi costing you about $10 less than from O’Hare. The CTA Orange Line runs from Midway, has fewer stops than the Blue Line and directly drops you downtown. From there it’s possible to walk or connect with a bus to your hotel. Make sure to pick up a 3 day CTA pass from the airport, Walgreen’s or metro stops downtown. Saves you money on public transportation.
Where to Start?
In Chicago there really is just one area that most tourist and business travelers stay. Just off Michigan in and around neighborhoods like Streeterville, the Loop, West Loop, and North Side. Hotel prices are somewhat pricey, average $200 -$300 a night. There are some hotels up in Lakeview and Lincoln Park but they are far and few between and most of the time just as pricey downtown.
Chicago has well established public transportation, so don’t be afraid of getting on a bus or the metro. Taxi prices in Chicago aren’t bad but you can definitely save serious money by just taking the L or a bus. Traveling along Lake Michigan is very easy and there are many routes you can take. Use Google Maps App for routes and times for Chicago public transportation.
As soon as you drop your luggage off at your hotel, you’ll probably be close to Michigan Ave, which is full of shopping. If that isn’t really your thing you could of course head over to Millennium Park and the Chicago Bean. It’s pretty and the park is tourism central but you only need about 30 minutes. In the summer Millennium Park hosts concerts at night where you can bring a small picnic with alcohol. Free and surprisingly fun.
Okay so the touristy clichés. Yes they are there and some of them are worth it. The Art Institute, Field Museum, Shedd Aquarium or the Planetarium are expensive to get in individually so buy the Chicago Pass. All museums are expensive and time-consuming so perhaps just pick one museum. Navy Pier and Sears Tower are very touristy and can be fun but I think you should skip them. Signature Lounge on top of Hancock Tower is free to get up and they have a bar and restaurant. Some of the best views in Chicago.
Also if you love architecture the you should sign up for one of the boat tours that leave in-front of the Wrigley Building on the Chicago river. Usually they last around 60 – 90 minutes and offer stunning shots of Chicago’s buildings. They have both night and day tours but make sure to go when it’s warmer since you’re outside of most of the time.
Like a Local
So you know about the touristy Chicago things but what about local Chicago? Lincoln Park is more for the locals and it is somewhat out-of-the-way from the downtown touristy sights. But I’ve always said this, it is perhaps one of the best features of Chicago! Stretching from North Blvd to Edgewater, Lincoln Park is huge and has its own free zoo, a golf course, several museums, tennis courts, and of course several beaches.
My advice, take a Divvy bike from downtown and ride along the lake shore up north. You can park the bikes at any of the free stations and it offers a cheap, relaxing way to see much of the city. Want to go to beach, just take a bike. Want to explore Lakeview or Lincoln Park? Well only 2 – 4 miles from downtown and on a bike would be a maximum 30 minutes.
Speaking of Lakeview and Lincoln Park, why these two neighborhoods? I live in Lakeview and it’s one of the densest neighborhoods in Chicago. With many locals around, it’s not too surprising that this is where some of the best restaurants and nightlife are located. The same goes with Lincoln Park and what I love about both is the examples of lovely Chicago architecture. Take your time to walk and explore!
There is also the more hipster part of town called Logan Square. Kind of further out and more inland, this is honestly not a place I would hang out but some people love it. You could also try Old Town, West Loop, and as far up as Edgewater where it becomes somewhat residential. However there is Hollywood beach up there that is more known as the “gay” beach if you’re gay and coming in the summer.
In the spring, summer and fall there is more to do and more open. Days last longer and more events are on the calendar. It’s possible to stumble on a festival like Gay Pride, Polish Parade, the Flower Show, a marathon, St. Patrick’s Day Parade, food markets, and many more on random weekends. Sometimes you get lucky and just walk up on it. Check out this website for updates on events.
However I also think winter can be magical here. By December snow has fallen and Michigan Ave is covered in beautiful Christmas decorations putting everybody in the spirit. Neighborhoods keep their cozy feel and Millennium Park comes alive with a skating rink and more decorations. In the loop at the Daley Plaza there is also the Christkindlmarket or Christmas Market. For the end of November after Thanksgiving and the month of December before Christmas, the market sells European goods and food and truly makes for a great Christmas setting.
Eating
We all know that Chicago is a food city, this is well established. Chicagoan’s know great hearty food, probably because with the amount of immigrants here; mostly from places like Poland, Italy and Greece. Most of the great food is located above the Chicago River in the neighborhoods of Streeterville, Near North, River North, Gold Coast, Lincoln Park, Logan Square, Old Town, Lakeview, Wrigleyville, and Uptown.
Below are some of the top choices to eat for breakfast, lunch and dinner. No particular order and most are scattered from the loop to northern Chicago near the Lakefront. If you’re starving and not near any of these restaurants below, I recommend that you pull a smart phone app with Yelp and search for a highly rated restaurant. With so much great food in Chicago, you should not have to settle for less.
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Breakfast
- Yolk – Try the strawberry orange juice
- Doughnut Vault – Best donuts hands-down
- Wildberry – 4th ranked restaurant in Chicago
- West Egg Cafe – Yummy American food downtown
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Lunch and Dinner
- Sultans – Cheap and fantastic Falafel
- Purple Pig – All things pig
- Alinea – Highest rated restaurant in Chicago; expensive but world-renowned
- Girl and the Goat – One of the hottest dinner choices
- Ann Sather – Swedish Cinnabons
- Wow Bao – Fast, lovely Asian buns
- Kuma’s Corner – Famous Chicago burgers
- Giordano’s – Obligatory deep dish pizza
- Native Foods – Wonderful healthy food
- Simply It – Vietnamese food in Lincoln Park
- Portillo’s – Chicago-style food
- Pho 777 – Vietnamese pho
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Desserts
- Cafe Vienna – Austrian pastries
- Sprinkles – Famous Chicago cupcakes
- Mollys Cupcake – Cupcakes and dessert
- La Fournette – French desserts and pastries
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Going Out
If you’re into nightlife, Chicago will not disappoint you. On a weekend the areas around Logan Square, Lakeview, Lincoln Park, Old Town and Near North are packed with all types of people going to all types of establishments. Really you must decide, what kind of person are you? Hipster, go to Logan Square. Everybody type of bar, Lakeview and Lincoln Park. More upscale, Near North.
By far Lakeview has the most bars but it’s not surprising since it also has the most people. In Lakeview there is Wrigleyville which is packed in the summer from tourist and locals catching a game at the Cubs stadium and then going to the many of hundreds of bars in the area. It’s really not my thing and if I’m at a bar it’s usually right next to Wrigleyville in Boystown on Halsted.
Yes I’m gay and if you’re gay and looking for a good time, to meet someone, or just dance, Boystown is that place. Many older gays will tell you that Andersonville is also a great place to go but there isn’t the variety like there is in Boystown. There is something like 50 plus bars but I spend most of time at bars like Elixir, Roscoes, Sidetracks, and Hydrate.
Now if the Lakeview sports and gay bars or the college atmosphere in Lincoln Park are not your scene, you could also try Logan Square/Wicker Park known to be more electric and hipster. Some good ones include, Violet Hour, Lost Lake, Handlebar, and Analogue.
If clubbing is not your thing you could grab a lovely glass of wine and chill at I/O Urban Roofscape, Signature Lounge at the Hancock Tower, or Tavern at the Park. All offer great views of surrounding downtown Chicago and well-known to deliver a great experience.
A Weekend in Chicago
Chicago is such an underrated city and has many wonderful things going for it. The music scene, four distinct seasons, the food, the obsessive drinking, and the mostly friendly people. The city is a city that knows it’s great yet nobody comes off as pretentious about it. It’s huge with skyscrapers yet certainly not daunting like you would expect.
So you won’t be disappointed with this city and in fact you’ll be pleasantly surprised. Most of the time it’s overlooked by New York or Los Angeles but honestly it has everything those city offer plus its own separate unique character. You can’t do it all here in a weekend, but you can understand this city greatly and learn to love it like the locals do.
images by: shawnvoyage
