While we live in one of the most popular vacation destinations in the world in Miami, we all know what our summers are like; hot, humid and traff-icky. And that’s why it’s always a good idea to break up the time spent at the beach or alongside the pool in our little paradise, with quick get-aways to places where the weather is a net positive, not a debilitating negative.
Each issue Whealthy Magazine takes a weekend get-away to someplace fun and exciting, and we re-trace our steps here so you can follow in them if you like, or customize your own visit. And you don’t have to live in Miami to take our advice—you can fly in from anywhere. Remember, travel is healthy. It’s an opportunity to exercise your brain and your body in ways that you never do at home. Getting away from your daily routine and home-base also helps you decompress and unwind, which we all need to do as often as possible (have you seen our traffic?!). We hope you enjoy our visit to CHICAGO!
- Will & Wendy Whealthy
We flew out first thing Saturday morning but, of course, you can leave Friday at any time. The nice thing about American Airlines is it’s a hub in both Miami and Chicago O’Hare. Plus all the other airlines fly to the Second City, so there are almost 50 flights a day to Chicago, with many from as low as $150 for a non-stop return ticket. O’Hare is much larger and more unwieldy than the smaller Midway Airport, which is also closer to the city, so if you have the chance and the costs are similar, you’re likely better off with Midway.
We flew into O’Hare Saturday morning and took the taxi service American Flat Rate into the city. There are many types of taxis available to be summoned either from the curb or, as we did, from the phone kiosks ringing the baggage claim area. Our full-sized black car arrived within 5 minutes to pick us up curbside; for $69 it took us right into town. You can also use Uber for about $40 but the benefits of Uber are highly diminished at O’Hare because of the strict regulations imposed on the drivers. If you’re on a budget, the train is wholly acceptable and speedy. It’s also an experience: if you take a window seat, for good parts of the ride you can literally see into the homes of those who live next to the tracks. It’s a bit of a voyeuristic indulgence but this is America and those are your neighbors. Besides, you can spend the entire trip being thankful you don’t live on top of train tracks!
We arrived at our Michigan Avenue hotel by noon. We stayed at the Intercontinental in the area of Michigan Avenue known as the Magnificent Mile, but there are dozens of great hotels in this part of town which is, in our opinion, the absolute best part of town in a town full of great parts! We checked in early, an arrangement we had made in in advance, then changed for the ballpark and hailed an Uber to head to Wrigley Field for the Cubs game.
An Uber takes about 20 minutes from the Magnificent Mile and costs about $17-$20. You can also jump on the train for a ride that lasts about the same time and costs $3 and comes with 2 transfers if you take them within two hours of swiping. Regardless of how you get to Wrigley, it’s a good idea to buy a single-ride subway ticket before you walk into the game because you’re going to need it afterwards and you don’t want to be stuck in a long line with hundreds of inebriated Cub fans trying to figure out the ticket dispenser.
You can either buy ballgame tickets in advance from one of the ticket sites or MLB.com, or you can try your negotiating skills with the scalpers around the stadium. However, since the Cubbies are now World Series champs, and Chicago is arguably the most rabid sports city in America, waiting until you get to the stadium to buy tickets can lead to sticker shock. Thankfully Mrs. Whealthy is good at using Craigslist so we were able to get bleacher tickets for $65 a pop. We typically like to sit in the bleachers because that’s where many of the crazier fans (and lots of happy drunks) are found and you are immune from the corporate seats, whose occupants are always much more reserved.
If you’re not really into general admission with metal benches and no assigned seating, there are plenty of great seats all over the ballpark. There are still some obstructed views though, so head on over to WrigleyGuide.com to verify your seats if you’re concerned. In addition, unlike the dome we have at home in Miami, you will want to consider how averse you are to the summer sun. While it may not be a tropical climate, you can still get a Windy City-sized sunburn without much effort. So for some overhead protection choose the higher numbered seats in the first level, or (and this is much less expensive but requires you to channel Magellan), determine where the sun will be at the time you’re at the game and sit in the part of the stadium that won’t be affected for the entire game.
If you’re early to the game there are plenty of warm-up spots encircling Wrigley Field where you can literally rub elbows with hundreds of the Midwest’s rowdiest sports fans. We arrived just in time for game time so we went right into the stadium, grabbed some beers and brats (yes, it was Cheat Day!) and headed up to the bleachers.
One of the added bonuses of the bleachers at Wrigley is that, on hot summer days, the grounds crew will come out between some innings and spray those closest to the outfield fence with water from their water canon. This is a great treat if you’re dressed for it, so make sure you’re properly attired for getting a soaker if you’re sitting close to the field.
After the Cubbies won (W!), we headed across the street from the bleacher exit to Murphy’s Bleachers to wait out the mass exodus. If you’re going to do that, make sure you visit the restroom before leaving the stadium since 2000 of your new close friends will wait until they’re at the bar before doing so and you will spend an hour in line.
About 30 minutes after the game ends you’ll want to use that single-ride ticket you bought and head to the Addison station on the Red Line to go back into town. It’s around a 20 minute subway ride back to Grand Station and the ‘hood where you’ll be spending much of your time.
We returned to the now-bustling city for a drink at the Tortoise Supper Club, a quintessential Chicago bar and restaurant owned by lifelong Chicagoans Keene and Megan Addington. Then, after taking time to plan out our Sunday (Mrs. Whealthy is quite the planner), we headed up to our dinner spot, the upscale Lavelle Kitchen + Bar, which has amazing views of the city and was only a 5 minute walk from our hotel.
After dinner you should stop by the lobby of the Langham Hotel where Travelle is housed, which is equal parts Bond Street appointment and Chihuly Vegas glass.
The next day Mrs. Whealthy and I rose early and headed out for a run along the famous Chicago waterfront. We recommend you don’t run on the streets of Chicago since the blocks are short (having to stop every time can be annoying) and the drivers, while much more attuned to pedestrians and exercisers than those in Miami, can still be a hazard. Take the 7-minute walk in stride and enjoy the quiet calm of Chicago, because this will be the last you’ll see of that calm all day.
Along the lakeshore you can go north or south. If you go north, you’ll go past the Navy Pier where, if the weather is nice, you’ll see dozens of chess players along the route. If you go south you’ll want to stop at the Beaux-Arts Buckingham Fountain, which was dedicated in 1927 and is one of the largest fountains in the world. For those with a good memory, you might even recognize this landmark in Grant Park from the hit 90s hit show Married… with Children.
After our 5 mile run, Mrs. Whealthy and I headed to one of the greatest treasures in all of Chicago - Millennium Park, which, despite its name, didn’t open until 2004. This incredible landmark attracts 25,000,000 visitors yearly and is one of the most beautiful and functional urban green spaces in the entire country.
Go take a photo of yourself at The Bean, or “Cloud Gate” as it is formally called. It’s an incredible sculpture by Indian-born British artist Sir Anish Kapoor that attracts thousands of visitors daily. But be careful if you go underneath! You can whang your head like we saw one couple do. The sculpture can be a little disorienting with its house-of-mirrors quality.
If you’re into rock climbing or rollerblading and roller-skating there are two wonderful rock climbing walls surrounded by a roller-skating oval. There’s also the Lurie Garden which is an amazing inner-city accomplishment. If you’re lucky there will be a concert going on the Great Lawn of the Jay Pritzker Pavilion where you and 11,000 of your closest friends can lounge under the sun or the stars to be entertained by Bon Iver (June 3) or Robert Plant (June 17). Go to MillenniumParkFoundation.org to learn more about all that Millennium Park has to offer.
After about an hour of wandering around Millennium Park we had worked up an appetite so we headed to Siena Tavern. You might recall we had a Siena Tavern in Miami for a hot second, but this one is the original, and it is fantastic. Since we burned about 800 calories on our hour-long run (running will burn between 300-500 calories per half-hour if you’re doing it right) we spoiled ourselves with a Bloody Mary (Mr.) and a glass of champagne (Mrs.). The Bloody is one of the best around, so don’t be shy, just watch your sodium intake, which can be mostly accomplished by passing on the pickle and the olive that come as garnishes with the drink.
We split the kale salad and Mrs. Whealthy had the Avocado Toast, while I had something called a Breakfast Pizza (finally a dream come true, pizza for breakfast!). It was good, but large. Despite our best efforts to finish it we still had three pieces left (these are Midwest portions, not Miami Beach portions, so don’t be afraid to ask for a doggie bag). We promptly left behind our own to-go bag due to the aforementioned Bloody Mary and champagne!
After brunch we headed back to the hotel to shower and change before going out for an afternoon of culture. We again stayed within our little 4-block radius and walked down Michigan Avenue to the Chicago Water Tower which houses the City Gallery, a photo-museum and gallery inside a 19th century landmark. The ongoing exhibit is the perfectly suited Stand up for Landmarks! Protests, Posters and Pictures. If you’re not into photography there is also the Chicago Sports Museum located right around the corner. There’s also something that everyone has to do at one point or another: take the water-based architecture tour of Chicago. If you think the history is amazing from land, wait until you take a guided architecture tour. It is well worth the seventy-five minutes.
With the sun getting low on the horizon we hit a few shops on Michigan then headed to the famous Shaw’s Crab House and Oyster Bar for dinner. Shaw’s is great because you can either sit in the more formal fine-dining restaurant to the left of the hostess stand (Crab House), or you can hang a right and sit in the more relaxed diner-like area (Oyster Bar). They have different menus (the Crab House being much larger and more formal) so you will want to study them before making a decision. We opted for the more casual (and noisier) venue that also allowed us to keep posted on the various sporting events going on around the city and the country via the televisions hung unobtrusively around the restaurant.
We started with a dozen oysters for $36 (if you’re there between 4-6 PM all oysters are half price, or $18!). Shaw’s carries 12 oyster varietals, six from the east coast (Maine, Massachusetts, PEI, New York, and Rhode Island) and six from the west coast (Washington State). After our oysters Mrs. Whealthy ordered the Tuna Poke Tacos while I ordered the Seafood Gumbo.
The sun was down but the night was young so we hightailed it over to Sound-Bar a few blocks away to cut the rug for two songs and then, exhausted from a jam-packed day, we made it back to the hotel and fell into bed.
The next day we had an early afternoon flight out of O’Hare so we got up early for a quick walk around town and ended up at the wonderful Eataly for an early lunch; again, only a few blocks from our hotel.
If you’ve never heard of or been to Eataly (there is one in New York City) it’s a must-stop if you love Italian food and culture. It’s also great if you like cheese, meat, olive oil, cooking, beer, wine, and great customer service. We sat on a high-top on the second floor and watched the staff make burrata as we enjoyed a bottle of rosé ($41) which, for a dollar more, could have come with a nice charcuterie platter.
From Eataly we walked back to our hotel where we had asked for and were granted late check-out, then hailed an Uber to the airport. Keep in mind, Chicago is a massive city of 4,000,000 and the traffic is equally massive, so give yourself plenty of time to get to the airport. While O’Hare is notorious for flight delays, we still recommend leaving 75 minutes before you need to be at the airport because traffic in the middle of the day can be a nightmare.
While we left on Saturday and returned on Monday, you can also do this exact same trip leaving Friday and returning Sunday. It’s simply a matter of where you have to be and when.
All told, we had an incredibly rewarding and jam-packed long-weekend in the City of Big Shoulders. Just remember, if you never leave, you can never be happy to be home!
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