I live in the heart of “tourist town Chicago.” As Spring slowly threatens to arrive, despite Winter’s many efforts to hang on to every last bit of time in the forecast it can claim, the Chicago summer tourists are beginning to arrive. Having spent the last five years making this tourist neighborhood my home and in the spirit of the oncoming tourist invasion, I thought I would steer off course from the workwear discussion a bit and share with you some ideas that I think would make for a great weekend visit to The Windy City (called such for its very shady politics, despite the well-known strong breeze that comes in off Lake Michigan just about every day of the year).
Without furter ado, some of my favorite ways to entertain visitors through a local’s eyes:
Chicago Architecture Boat Tour ~ an absolute must and something I have done several times as we take all our visitors on this boat tour the first time they visit. It offers fantastic views of the city from a unique perspective and some great tidbits of information about the buildings from their knowledgeable docents. (Note: There are other companies that offer these tours, but the tours offered through the Chicago Architecture Foundation are my favorite.)
Skydeck Chicago @ Willis Tower ~ While the views from the top of the Willis Tower (traditionally known as the Sears Tower) aren’t necessarily different from those in other tall building observation decks, I highly recommend making a visit up to this observation deck to check out The Ledge. The protruding glass windows allow even the bravest of viewers to test their fear of heights when they step out on the glass windows with nothing between their feet and a free fall down 110 stories except a thick sheet of presumably extra safe glass.
Millennium Park ~ A tourist attraction for sure, it’s worth a stop to enjoy the new and well-maintained park in the heart of downtown. Be sure to step under The Bean, which I visited below (in a black dress and again in white pants) on early mornings midweek before the crowds hit the park, to check out your crazy reflection. After many peeks up, I still can’t quite tell how tall the inside is (you’ll know what I mean if you visit).
Oak Street or Ohio Street Beach ~ We experience one of the greatest parts of living in Chicago during our brief summer months when we can walk from a downtown high-rise to a lakeside beach in a matter of minutes. Beaches this nice with an urban backdrop like this one are few and far between. Be sure to wiggle your toes in the soft sand (and maybe dip your toes in the not-so-warm Lake Michigan water).
Olive Park / Navy Pier ~ A quick walk from Ohio Street beach (just a couple hundred yards, I’d guess) takes you to Olive Park where you can find great views of the city skyline (below is a photo I took from Olive Park). From here, you can easily venture to Navy Pier, if you’d like. The Pier also offers great views of the city skyline though it’s certainly a tourist trap. It might be worth a walk down the Pier if the weather is nice, but if you’re in a time crunch, this wouldn’t be my first stop unless you’re really interested in some great skyline and lake views.
Walk Along the Riverfront ~ The city built a great riverwalk along the Chicago River. You can walk along the north side of the river, but I think you’ll find a prettier walk along the south side, where I took the photo below. The south side riverwalk will also take you out to the Lake where you can follow the path along Lake Michigan, which is great. Getting to the riverwalk can be a bit tough to find, so look for stairs or walkways down to the riverfront at State Street and Wacker Drive, Michigan Avenue and Wacker Drive, or Columbus Avenue and Wacker Drive, among other places. Nearly every time either my parents or The Man’s parents visit, we end up talking a stroll along the riverfront to enjoy the peaceful waterfront views.
Wrigley Field ~ For sports fan, it’s an obvious spot on the hit list. I’ve added it to my list in case you’re a sports fan (because it really is an interesting historic site). But if sports isn’t your thing, I’d pass this up for something more up your alley.
Second City ~ A breeding ground for some of comedy’s funniest folk like Tina Fey, Steve Carrell, Amy Poehler, and so many others, this sketch comedy establishment provides regular evening shows that always leave us laughing. Be forewarned about a few things:
- Definitely buy tickets at least a few weeks in advance. The shows almost always sell out, at least in my experience.
- I think the Mainstage is funnier than the e.t.c. stage. You can check their website to find out which show works better for you, but I’d definitely recommend the Mainstage if it’s available.
- The humor can be a bit dirty. It’s not a show filled with vulgarity and filth and all comedians remain fully dressed in very conservative clothing the entire time, but if your comedic tastes lean more toward a conservative nature, be cautioned that this may not be for you. I think it’s absolutely hilarious, but I also have a reasonable tolerance for cursing and off-color humor.
Museum of Science & Industry ~ It’s massive, so don’t plan to see the whole darn thing in one day. The building was part of the World’s Fair Grounds in 1893 and even today is impressively enormous. Locals and tourists alike love and appreciate the amazing exhibits in the museum. So especially if you visit during a time of year when the weather may not be particularly cooperative, this is a great option to explore one of Chicago’s best museums.
Two blocks from my apartment, I regularly walk past a Chili’s restaurant. I don’t have a particular issue with Chili’s, but it kills me every time I hear a family of tourists discussing Chili’s as a dinner option while standing on a corner looking for a place to eat. Chili’s??!! In my neighborhood, I’d surmise we have over 50 unique and tasty restaurants within a 6 block radius, and these families came all the way to Chicago to eat something they can grab in their own town??! So please, if you come visit, don’t eat at Chili’s. Save that meal for a random Friday night in your own town. Instead, consider one of these options:
Brunch ~ Very popular in Chicago, especially during the summer, feel like a local during your visit and grab brunch while in town. Know that if you arrive on a Saturday or Sunday morning after 10 or 10:30 am, you’ll likely have to wait a bit. And most of the brunch spots don’t take reservations
- Bongo Room ~ They have a couple of locations. While their menu includes some traditional breakfast fare, they always have some decadent brunch options as well.
- Wishbone ~ Another brunch favorite of locals, it has a bit of a southern flare. A peek at their menu will give you an idea of what to expect.
- ZED451 ~ This option takes a bit more explaining. It’s certainly pricey, but The Man and I have been on a few occasions and believe it’s more than worth it’s price tag. Be ready for a high end combination of buffet-style sides and desserts (a serious selection of gourmet options) complemented by nine courses of served main dishes like buffalo chicken and waffles, cinnamon rolls, and frittatas. Arrive hungry and you will leave more full than you’d imagined.
Lunch / Dinner ~ Below I included a small sample of my favorite spots in my neighborhood. The city offers far too many options for me to include an extensive list of great choices.
- Chicago Cut ~ The city has “a thing” for steakhouses, so they dominate the town’s restaurant scene. This local spot is my favorite (and President Obama grabbed dinner there last week too, so it can’t be that bad, right?)
- Mercadito – Fancy Mexican. And be sure to grab a margarita – they’re great!
- MK ~ A little off the beaten path with good variety of great food on the menu. You can’t go wrong.
Mid Range ~ A few tasty options that aren’t quite as expensive. Their menus will speak for themselves, I believe.
- Xoco ~ Rick Bayless’ version of well-done Mexican street cart food (that sounds worse than it is; the food is actually more high end than that description seems to imply). The Man and I have been for breakfast and dinner and loved every meal. And I ALWAYS get a Limonada (one of my favorite drinks from around).
- M Burger ~ Burgers, Fries, and Milkshakes: a tiny spot with a few indoor seats and a slightly larger outdoor seating area. The food is decent for a local, organic, fast-food type burger joint.
- Sopraffina ~ A slightly nicer quick stop to grab some food, the Italian-inspired salad, sandwich, pasta and pizza locale brings a bit of a gourmet touch to a quick and easy bite to eat without breaking the bank.
- Portillo’s ~ This Chicago establishment specializes in hot dogs and Italian beef. You can also grab a VERY LARGE beer, if that’s up your alley. Although there are locations all over the city and suburbs, I think the location at Ontario and Clark in River North has the most character. The menu offers a wealth of other options, but it’s all fast food from a traditional Chicago hot spot.
- Rock ‘n’ Roll McDonald’s (600 N Clark St) ~ I can’t say I visit here frequently. I think I have been twice in my five years living here, but a two story fancy McDonald’s may at least be worth talking a stroll past if you’re not into grabbing a Big Mac and fries.
Deep Dish Pizza ~ Everyone who visits Chicago asks about deep dish pizza. While I think it’s great on occasion, we don’t visit often. But when we are in the mood for some very filling pepperoni and cheese deliciousness, these are my two favorite options. You can likely find many Lou Malnati’s around town and this is much more popular with tourists. Pequod’s has one location in a neighborhood a bit north of downtown and is much more of a local spot. The city has several other deep dish hotspots, but I don’t love them, so I’d recommend one of these two.
Dessert ~ Very popular in Chicago, gourmet donut shops are having a moment in this town. I know traditionally one might consider a donut breakfast fare. But really, it’s more of a dessert when considered for what it truly is. The two options below stay open late on the weekends to provide dinner patrons a place to stop for a fun and tasty non-traditional dessert. So if you’re going to one of the brunch spots above, consider a donut for dessert.
- Firecakes ~ If you love a light and airy glazed donut, this place will meet your needs. I LOVE the Vanilla Iced with White Chocolate Crisps. I shared about it a while back and have had probably more than my fair share since my first visit, but it’s delicious!
- Glazed & Infused ~ Everything on their menu tastes great, but I think the cake-type donuts are the best on their menu. If I’m looking for a denser donut, I’ll likely hit up Glazed & Infused, while I’ll walk down the street to Firecakes when I’m yearning for a light and fluffy sugar rush.
First off, if you have the same store near your home town, don’t shop in Chicago. Sales tax rates here are insane, and you won’t be scoring any great deals on Michigan Avenue that aren’t in your hometown store too. But, if you’re looking for some unique options, here are a few to consider:
Michigan Avenue (north of the river) & State Street (south of the river) ~ Here you will find many of your standard chain stores, some higher end and some your standard fare. They are practical but nothing to make a focus of your vacation, in my opinion.
Oak Street (just off Michigan Ave) ~ A very high end stretch of shops in a neighborhood called Gold Coast. The area includes some high end major retailers as well as some local boutiques.
Armitage Ave ~ A bit north of the downtown and tourist neighborhoods, this much more local area has some small boutiques (at various price points) as well as some reasonably priced consignment shops. You can jump on the L’s Brown Line and get off at the Armitage stop to land right in the middle of this shopping area. There are plenty of great local restaurants sprinkled throughout this area as well to make a day of it.
Randolph Street Market ~ a vintage flea market that opens once a month for a weekend in the West Loop neighborhood. I have been a couple of times and it’s hit or miss depending on what you’re searching for, but there are certainly no shortage of vendors. You will find a wealth of vintage and antique dealers as well as some independent boutiques.
Le Thrift Consignment Boutique ~ I love checking out thrift and consignment shops in other towns, so this would be up my alley. Consider stopping by if you’ll like these types of stores as well.
Luxury Garage Sale ~ Similar to Le Thrift, this luxury consignment boutique will still run you a pretty penny (in my opinion) considering they favor high end brands that command high end prices. But you can certainly score better deals than buying these items new if high end fashion is your thing.
Fashion Outlets of Chicago ~ A new addition to the area in 2013, this outlet mall is located right near O’Hare airport and has a wealth of outlet stores for very high end retailers like Barney’s, Tory Burch, Neiman Marcus, and so many others. They still command some decent prices, but may be worth a visit if you favor high end brands.
Divvy Bikes ~ A shared bike system that came to Chicago last summer, it’s a great way to travel around the city and be able to cover a bit more ground than your own feet could tread while still having the benefit of seeing all the sights along the way. Be sure to read their signs, though, because these bikes are geared toward short trips and not all day rides around town.
Cabs ~ Super easy to find and much easier than trying to park a car. Street parking can be hard to come by and parking garage rates are crazy expensive, so if you can avoid having a car, I would recommend it. (Consider Uber or Hailo cab services as well)
Parking ~ If you do need a car, check out local start-up Spothero which might be able to save you some serious loot on your parking spot. It’s a bit like Orbitz for parking spots.
The L ~ Pretty convenient, especially for downtown travel, and generally easy to use. It’s safe and pretty clean, in my opinion (as long as you stay in safe neighborhoods, and it’s pretty hard to accidentally end up in a rough part of town in Chicago). Just be forewarned, if you have a stroller, that not all stops have elevators and are handicap accessible. If you’re on your feet, no worries, but just something to keep in mind.
If you have additional questions or more specific requests, please don’t hesitate to reach out and email me. I left many options for food and activities untouched but could post forever about all the things to do and places to eat. Chicago is a great city and wonderful place to visit, especially during the summertime. Hopefully you’ll make it to The Windy City soon!