Behind the wheel of a stranger’s car, I adjusted the seat and mirrors, even as my adrenaline told me that it was wrong. I didn’t know the car or its owner. Then I started the engine and pulled into Chicago traffic.
My husband, riding shotgun on our way out of town, hit the “begin trip” button on my phone’s Turo app, a platform that lets travelers rent cars from locals. Moments earlier, a man named Gabriel had pulled up to our hotel, dropped the keys to his sedan in my hands and walked off with a casual farewell — as if this was normal.
It was our last day on an autumn weekend trip to the Windy City, where we skipped the usual rental car. Instead, we hopped in Uber cars and cabs, cruised in a water taxi, walked and rode on “L” trains, the city’s rapid transit system.
Chicago has ample old-school transportation options, and the sharing economy has added new ways to get around. Together, they make Chicago easy to navigate — with the help of locals and without the stresses and costs associated with mainstream car rentals. My family, including my husband and our 9-month-old daughter, were ready to test-drive the modern world of ground transportation.
The weekend began as many Chicago trips do: lurching through traffic in the back seat of a cab. Especially on a weekday, catching the train at O’Hare International Airport can be a cheaper and faster way to reach downtown. But we landed under a dripping sky, and the thought of schlepping a car seat, stroller, bags — oh, and squirmy baby — through turnstiles, train cars and several city blocks in the rain sounded exhausting.
A $49 cab fare hurt, but a $60-a-day fee to park a rental car at the hotel would’ve hurt more. I love saving money almost as much as I love saving time, and this anti-car-rental weekend was already checking both boxes.
Price of the ride
|City||Miles Traveled||Uber X||Taxi|
|New York City||9.9||$40||$49.50|
|Santa Monica, Calif.||3.3||8.11||12.15|
*This trip was taken during rush hour. During particularly busy times, Uber charges a premium. The practice is called surge pricing.
Uber there, taxi back
To ease our carless ways, we chose a centrally located hotel off Chicago’s famed Magnificent Mile. First stop: the West Loop, a restaurant-rich neighborhood, for dinner.
To get there — two miles away on the far side of the Chicago River — I pulled out my phone and clicked the ride-sharing app Uber. Within 10 minutes we were stepping out onto Randolph Street, where the Friday happy-hour vibe was spilling onto sidewalks.
We grabbed a drink at Haymarket Pub and Brewery, then snagged a table before the dinner rush at Little Goat Diner, a kid-friendly sister restaurant to the famed Girl & the Goat. After filling our bellies with dishes like tempura mashed potatoes with kimchi, we ambled down the popular street, absorbing the energy of a city welcoming its weekend.
Sensing a baby on the brink of bedtime, we decided to head back to our hotel just as I saw a parked cab. It was time to use the old-fashioned “hail-a-taxi” method.
I usually arranged rides using Uber, which provides the driver’s name and service rating, plus the cost of the trip (as does its main competitor, Lyft). Without that information, I was wary and hesitant when I approached the taxi. Before I could walk away, though, he gestured for us to get in.
My unease quickly gave way to amazement as he hurtled toward our hotel on an unexpected and efficient route, navigating Chicago’s busy thoroughfares with only the name of a hotel as his guide — no address or smartphone map dictating directions. His maneuverings felt like wizardry.
Ride a water taxi
We woke up on our first full day in Chicago with the goal of not just seeing the city, but really experiencing it — and that seemed easier to accomplish without an isolating rental car. We’d need to travel with locals.
Uber and Lyft
By Kerri Westenberg
Uber and Lyft work similarly: Users download an app on their smartphone and use the app to request a ride. Both show the price of the ride before you hit “confirm,” and then let you follow along on a map as your ride approaches. Both also offer upgraded services for higher prices; prices pop up for each type of available service when you request a ride so you can choose among them before you confirm the ride. Lyft offers Lyft Lux, with high-end vehicles for four passengers; Lux Black, with premium black car service; and Lux Black XL, with premium black SUVs that seat up to six. Uber has UberX, the basic service; UberXL, for up to six passengers; UberSelect with luxury vehicles for up to four passengers and UberBlack and UberSUV. The company recently introduced UberPool for low-cost ride sharing. Lyft users who accrue Delta SkyMiles, take note: You can link your Lyft and Delta accounts to earn miles while you hop around town.
Lake Michigan beckoned my water-loving husband and me. Tucking the baby into her stroller, we made the one-mile walk from our hotel to Navy Pier, scanning for doughnut shops along the way.
We took a lap around the pier’s perimeter — relishing the views of the city rising from the water — and then moseyed to the Chicago Riverwalk.
That’s where we encountered a novel transportation option in this lakeside city. Several ferry companies operate on the Chicago River, some designed for tourists and others for commuters who use the boats to bypass bottlenecks at the city’s busiest roads.
At the Michigan Avenue Dock, near the famed Wrigley Building, we chose the Chicago Water Taxi company, with bright yellow and black boats reminiscent of street taxis. We bought $10 unlimited day passes per adult and hustled down the steps to the loading ramp, where we boarded a boat to Chinatown.
Weekend leisure cruises, double-decker architectural tour boats and privately chartered boats of raucous parties packed the river’s main channel. Chicago’s water taxis don’t offer frills, but are efficient and punctual. They also give passengers a relaxing float trip through the heart of the city and beyond for a low fee.
After the stop near Willis Tower, the river crowd thinned and the scene transitioned from polished corporate facades to industrial, low-slung buildings.
Rusted railroad bridges signaled the entry to Chinatown. We disembarked at Ping Tom Memorial Park with stomachs growling and headed toward the district’s commercial center in search for lunch.
Joy Yee Noodles — with a long line of locals — was the perfect lunch spot. After we dined off a vast menu, the friendly staff assured me the rice explosion beneath my daughter’s highchair was not a problem.
With midday drowsiness setting in, we caught the next water taxi leaving Chinatown, and returned to our hotel.
Hours later, we were reinvigorated — and thinking about food again. After a day of gallivanting around town, we opted for a one-block stroll to the original Gino’s East, counted among the elite of city’s famous deep-dish pizza institutions.
Rent a stranger’s car
Before our trip, I’d reserved a car for Sunday through Turo, an app-based platform likened to Airbnb for cars because users rent cars from individual owners. The one I chose — a 2017 Toyota Corolla — was just $56 for all-day use and up to 200 miles.
As our reservation was scheduled to begin, Gabriel, the car’s owner, texted through the app that he was on his way and would be at the drop-off point in 10 minutes. We hurried down to the hotel’s curb, early enough to watch him pull into the loading zone right on time.
After two days of being driven around by other people, Turo offered some control and a longer geographic leash, which we used to visit the expansive Chicago Botanic Gardens, about 25 miles north of downtown. Our route was a joy, skirting the lake along the way.
After a day and a half in the hustle and bustle of Chicago’s urban canyons, the wide-open spaces and tranquillity of these perfectly curated gardens was a welcome retreat.
We left with time to spare ahead of the car return, refilling the gas tank as we neared our hotel.
I set the reservation to end at 5 p.m. Gabriel walked up to our hotel at 5:02 p.m. as I uploaded pictures of the car in the Turo app to check it back in and document its returned condition.
That night we walked to the nearby train station and took the underground Red Line, then transferred to the elevated Green Line on our way back to the gastronomical West Loop.
My daughter found train-riding endlessly fun, so we returned the same way. On the “L” platform waiting for our ride, we stood between a setting sun and the city’s glass skyscrapers reflecting red, orange and pink light.
The next morning, the alarm went off at 3:15 a.m. and I’ve never been more grateful for Uber, which offers door-to-door ease at such an unholy hour. I was yet again thankful to avoid the hassle and time that would’ve been needed if I had to return a rental car and catch a shuttle to the terminal. Plus, the local driver gave us one last brush with Chicago.