When I have first-time visitors this is the itinerary we do that guarantees a perfect Chicago vacation.
After nearly three years at Concierge Preferred it is with great sadness that I’m leaving this great company and city. I will be moving to Pittsburgh with my wife. However, as a parting gift I’d like to offer the Chicago itinerary that I’ve perfected over the years for first-time visitors. I’ve had over a dozen friends and family members visit during my time here, and not only have I had great reviews but I never get tired of giving it.
Note: This itinerary assumes you’ll have clear skies and good walking weather. If you visit and find yourself in one of Chicago’s many weather moods adjust accordingly. Also this itinerary is best for a Thursday through Sunday visit.
Thursday: Arrival Day
Assuming they arrived into O’Hare or Midway in the afternoon time, visitors always feel frazzled the first day because a lot of the day is already lost. No worries. I’ve got you covered.
After dropping off your bags at your hotel, head to Xoco if you’re looking for a quick bite to eat.
Xoco, 449 N. Clark St., is a great Mexican spot in River North from Rick Bayless, winner of Top Chef Masters and many James Beard Awards. Xoco is next door to two other Bayless eateries, Frontera Grill and Topolobampo. Both are great restaurants, but I favor Xoco because it’s more casual, much cheaper, and of equal quality. My go-to here are the tortas—especially the Pepito, which includes braised short ribs, caramelized onion, artisan Jack cheese, black beans, and pickled jalapeños.
Knowledge nugget: If you’re wondering how the food is so fresh part of the reason is the rooftop garden that helps provide peppers, tomatoes, and other vegetables for all three of Bayless’ restaurants. Also, Bayless is the younger brother to sports pundit Skip Bayless.
After filling up catch a cab to the Willis Tower.
Skydeck Chicago, 233 S. Wacker Dr., is a Chicago icon that features the cool and terrifying Ledge that stretches out over 4 feet with a clear bottom where you can look down the 1,353 feet to the street. Lines tend to get long at Skydeck but being that it’ll be a Thursday afternoon you’ll be a bit better off than visiting during the weekend. The Willis Tower is also my favorite to visit during the latter part of the day because it’s breathtaking to watch the sun go down and the city light up from that high above it.
After the Willis Tower admire some of the Loop’s architecture.
Check out the site of the world’s first Skyscraper at the Field Building, 135 S. Lasalle St. At the end of Lasalle Street you’ll see the Chicago Board of Trade Building, and the street might remind of you of some scenes from “The Dark Knight.” Also, check out the lobby of The Rookery Building, 209 S. Lasalle St., which was designed by famed architect Frank Lloyd Wright.
After walking around the stomach might start to grumble again, so it’s time for deep-dish pizza for dinner.
Deep-dish pizza is best had on the night where you’re not planning on doing much after dinner because deep-dish pizza demands a lot of your body. The first night is usually the best because you’re likely tired from all the traveling and exploring and want to save your energy for the rest of the trip.
My favorite deep-dish pizza is from Gino’s East. The original location is in Streeterville at 162 E. Superior St., and it’s cool because of the graffiti covered walls. However, the wait there can be long, so if it is just head to the one not far from there at 500 N. Lasalle Dr. The River North location might not have the graffiti but it has a brewery and a stage making it an excellent way to mix in a little nightlife in your dinner. Where Gino’s pizza shines above the other options is the crust. The dough recipe is a secret, but some have thought there is cornmeal in it, which gives it an added layer of flavor.
Knowledge bomb: You can get the sausage on the pizza as a patty. They flatten out the sausage into a disc guaranteeing a bite of sausage in every bite.
Friday: Time to Walk
Most vacations don’t require some physical training beforehand, but you might want to get some walking done before heading to Chicago because there is no better way to see the city. This is the one day that you don’t want to skip.
You’re likely still going to be full from last night’s deep-dish pizza, so start out with a light breakfast of doughnuts.
Chicago’s got countless delicious doughnut shops, but my favorite is Glazed and Infused. The first doughnut to run out is the maple bacon long John, so make sure you get there early because it’s one you don’t want to miss. There are many locations across the city, but I recommend visiting the one in the Raffaello Hotel, 201 E. Delaware Place, because you’ll be close to the next stop.
After breakfast head to the John Hancock Center, for another spectacular view of the city.
You’d think after being at the Willis Tower you wouldn’t need to visit another tower, but the Hancock Center, 875 N. Michigan Ave., provides a completely different view. While the Willis Tower let’s you see everything from above, the Hancock Center not only let’s you see things from above but also provides the feeling of being among the high-rise buildings in Streeterville and River North. You have two options for seeing the view here. 360 Chicago offers great seating, a small bar, and TILT, Chicago’s highest moving attraction with guaranteed fantastic views. Your other option to see the view are the Signature Lounge at the 96th where you don’t have to pay for admission but do have to pay for drinks.
You’ve seen Chicago from up high but now see it from the street on the Magnificent Mile.
Head toward the Chicago River and before hitting your favorite stores don’t miss the Historic Water Tower, 806 N. Michigan Ave., and the Pumping Station across the street.
Knowledge pearl: These are one of the few buildings to survive the Chicago Fire of 1871.
After the history do a little shopping. I’m not a fan of shopping but one store I always stop into is Nike Chicago, 669 N. Michigan Ave. Not only does the store have every sneaker Michael Jordan wore during his six championships, but there is a centerpiece chandelier by Michael Murphy made of individual aluminum, gold-plated Air Jordans that when seen from afar look like the Jumpman logo.
After some shopping, experience some more history at the Tribune Tower, 435 N. Michigan Ave. It’s always fun to walk around the outside of the building and spot the fragments taken from other historical places and see them implemented into the tower. You’ll spot parts of the Berlin Wall, Vatican, Taj Mahal, the Great Wall of China, and much more.
Once you’ve walked all of Michigan Avenue give your feet a break and take an architecture cruise.
These tours offer a great way to take advantage of the Chicago River and experience so many breathtaking architectural styles from a one-of-a-kind vantage point. The tour from the Chicago Architecture Foundation River Cruise Aboard Chicago’s First Lady Cruises, 112 E. Upper Wacker Dr., highlights the history and design of over 50 buildings all from expertly trained docents. I’ve also done the architectural cruise from Shoreline Sightseeing, which was recently voted the most popular tour in America by TripAdvisor.
You should be hungry by now, so get some lunch.
If the restaurants and bars are open on the Riverwalk head there to continue to gaze at the buildings along the Chicago River. Depending on wait times I either head to Tiny Tapp, 55 W. Riverwalk South, for some bar food along with craft beer and cocktails, or City Winery, 11 Chicago Riverwalk, for a nice glass of wine and some light sandwiches.
When the Riverwalk isn’t open I head to Latinicity, 108 N. State St. Artisanal tortas, sushi and ceviche, chaufas, fritas, tacos, and sopas, are just a some of the never-ending options at the various stalls inside Latinicity. With several stalls to order from the wait is never too long, and you can still eat with friends and enjoy a pisco sour, tequila, or sangria from the bar.
Walk off your lunch and head to the Chicago Cultural Center.
You can walk into the Chicago Cultural Center, 78 E. Washington St., every day for a year and experience a different event, exhibit, or performance. The go-to stop in the center is the Tiffany dome. Measuring 38 feet in diameter and made of 30,000 pieces of glass, this is the largest stained-glass Tiffany dome in the world.
Knowledge petal: After the Chicago Fire of 1871 a group of English donors gave Chicago over 8,000 books to restore their public library. The thing is that Chicago never had a public library but with all these books decided to build one and it eventually transformed into the Chicago Cultural Center.
Cross the street and explore Millennium Park.
This is the best itinerary to explore the great attractions at Millennium Park, 201 E. Randolph St. Start off at Cloud Gate and take a photo on the side that faces the buildings so you can catch a great view of both the Bean and the Loop. After Cloud Gate head to Crown Fountain and admire the children playing in the water. Don’t be shy, and feel free to take off your shoes and enjoy the cold water and cool off your feet from the walking. After Crown Fountain, go to the Lurie Gardens and zigzag through the beautiful flowers before heading to the Frank Gehry-designed Jay Pritzker Pavilion.
Feel young again at Maggie Daley Park.
After you’ve explored some of the park, head over Frank Gehry’s BP Pedestrian Bridge to Maggie Daley Park, 337 E. Randolph St. On the surface this seems like an oasis for children, but after a few moments no park will make you wish you were a kid more than this one. Where do you start? The skating ribbon, rock climbing wall, mini golf, play garden, or the tennis courts—it doesn’t matter where you start but you surely won’t want it to end.
It’s dinner time in the West Loop.
After you’ve gone back to your lodging and rested, head to the West Loop for what might be the best strip of bars and restaurants in the city. There are a lot of fancy places, but I like to take guests to Green Street Smoked Meats. Everything from it’s warehouse-setting to the beer sink to the mouthwatering brisket makes Green Street Smoked Meats an excellent dinner spot in the West Loop.
If you want to feel fancy, cross the street and grab a cocktail at The Allis in the Soho House, 113–25 N. Green St., after dinner. I always enjoy the Redbreast 12 year, but their Eastern Standard cocktail is also very good.
Saturday: Chicago from South to North
This is an opportunity to explore some areas outside of Downtown Chicago that will give you a taste of what to see on your second visit.
Crack some eggs for breakfast.
Yolk is the go-to breakfast spot in this itinerary and with six locations in the city it isn’t hard to find one without a wait. There’s no magic to Yolk. They just know how to do everything right. Also, if you’re feeling boozy feel free to bring in some bottles of Champagne as Yolk is BYOB. Just make sure you eat enough because it’ll be a while until you have lunch.
Get your museum on.
No visitor has regretted every going to the Museum of Science and Industry, 5700 S. Lake Shore Dr. Located in Hyde Park, the drive down will give you the urge to explore it more on your second trip to the city. Known as being the largest science museum of the Western Hemisphere, the Museum of Science and Industry houses a Boeing 727, a 40-foot water vapor tornado, and a chick hatchery. However, one activity I highly recommend doing is the tour of U-505 German submarine.
Head back outdoors to one of Chicago’s most beautiful parks.
Grab a cab from the museum and head back north to Lincoln Park. It’s best to start at the corner of West North Boulevard and North Clark Street and head north through the park. See the Lincoln Monument, stroll along the Nature Boardwalk, say hi to your favorite animals at the Lincoln Park Zoo, smell the flowers at the Lincoln Park Conservatory, and relax in the peaceful Alfred Caldwell Lily Pool.
Fun Fact: Lincoln Park used to be a public cemetery, but citizens demanded it be changed once they realized it’s not such a good idea to have the remains of cholera and small pox victims in shallow graves near the lake.
Time for a Chicago-style hot dog.
After visiting the Lily Pool walk along Fullerton Avenue and stop at Chicago’s Dog House, 816 W. Fullerton Ave. It’s about a 20 minute walk but you don’t notice it as you’re walking through the beautiful homes of Lincoln Park. You’ll definitely be hungry once you arrive at Chicago’s Dog House. This small diner feels like the spiritual successor of the much-missed Hot Doug’s. They make a killer classic Chicago-style hot dog but also offer specialty dogs like the Mayor Daley, which comes with Irish cheddar, caramelized onion, and smokey Dijon, and gourmet dogs like the smoked alligator sausage. I always recommend to order a classic Chicago-style hot dog and one of the specialty and gourmet dogs for lunch.
Hit the Ball Park
Walk a block and catch the Red Line at the Fullerton Avenue stop and get off at Addison to enjoy a bit of sports history at Wrigley Field, 1060 W. Addison St. If you’re lucky enough to have a ticket to the game then enjoy it. If not, do the Wrigley Field Tour that provides a look at over 100 years of history at Wrigley Field including the clubhouse, press box, dugout, sections of the field, and more. Even if you don’t do the tour it’s still worth it to visit the stadium and get a picture in front of the marquee.
Grab a much deserved drink at Slugger’s, 3540 N. Clark St. This bar provides a pretty typical Wrigleyville experience especially if there is a Cubs game on. They offer great craft beers from breweries around the city. However, the hidden gem here is the batting cages on the second floor. No matter the age, every visitor that has done this itinerary has taken a swing.
Time to visit the Sandwich King
At this point you’ve dipped your toes in Hyde Park, Lincoln Park, and Wrigleyville. It’s time visit Wicker Park. After you’ve returned to your lodging for some rest and to get changed, grab a cab or take the Blue Line and get off at the Damen Avenue stop to eat at Pork and Mindy’s, 1623 N. Milwaukee Ave. This casual spot comes from the mind of Food Network’s own Sandwich King Jeff Mauro. The Bao to the Pork is the classic with its pork shoulder topped with daikon, carrot, cucumber, jalapeño relish, and Asian plum sauce on a steamed bao bun. I recommend everyone getting a different sandwich and splitting them.
The food will build a base for all the drinking. There is no science here. Just go up and down Milwaukee Avenue and have one drink in every bar. Don’t skip out on The Revel Room, Nick’s Beer Garden, and the Emporium Arcade Bar.
You likely don’t have much time today, so if you can try to squeeze in at least one meal and one activity.
Treat yourself to brunch.
Breakfast doesn’t always have to be bacon and eggs and nowhere is that more true than Mindy’s Hot Chocolate, 1747 N. Damen Ave. From James Beard Award-winning chef Mindy Segal, comes this eatery that for brunch takes your typical breakfast items and adds some sophistication that is a treat for both your eyes and your mouth. The duck and waffle is not to be skipped along with the famous hot chocolate.
One last view of Chicago.
End your trip at the Centennial Wheel at Navy Pier, 600 E. Grand Ave. This new wheel was built to celebrate Navy Pier’s 100th birthday. The wheel is 196-feet high and provides a unique view of the Chicago skyline from Lake Michigan. Its a great reminder of how beautiful this city is and why you have to come back and conquer the rest. No one should ever stay a Chicago first-time visitor.
This itinerary while a lot only gives a glimpse of what Chicago has to offer. Even after four years there is still so much that I wasn’t able to see.