Chicago, Illinois in 9 Hours 20 Minutes

Additional Photos by Jessica Bissa

City Highlights

• City: Chicago, Illinois, USA

• Population (metro): 9.62 million

• Known for: Sears (Willis) Tower and other architecture, The Bean, 24 public beaches on Lake Michigan, deep dish pizza, the third largest city in the United States and largest in the Midwest

• Distance traveled (on foot): 12.26 km (7.62 mi)

• Weather during visit: Partially sunny, 20-25ºC (68-77ºF)

• Time in Place: 9 hours 20 minutes

Chicago! Chicago! It’s a city that’s inviting and a city that’s exciting. Home to world-renowned museums, a thriving music scene, and architectural delights, the largest city in the Midwest has plenty in store for those who visit its windy avenues. While my travel partner and I were only exploring the city briefly and with a specific target in mind, there was enough to explore for years. Even though I grew up relatively close to Chicago, there were a variety of things that I had never done or experienced before on previous trips. With such a sprawling and varied cityscape, there is always something new to see.

While Chicago was not the original destination for this trip, my travel partner and I made the most of it after getting stuck at the airport. Quickly throwing together a plan of what we wanted to see in the city while we waited for the next flight, there was more than enough to keep us interested and engaged for just under 10 hours while we were there.

Arriving in Chicago

Getting There

Chicago is a significant transportation hub for the Midwest and the country. Chicago’s Union Station is one of the largest rail stations in the nation. Long-distance Amtrak trains bring travelers from Seattle, Los Angeles, Dallas, Washington, New York, and everywhere in between. While Union Station primarily services long-distance trains, several commuter rail options exist from other stations, such as Millennium Station or Ogilvie Transportation Center. Shorter distance options include South Bend via the South Shore Line, Kenosha and other suburbs via Metra, and Milwaukee, Detroit, and St. Louis via frequent Amtrak service.

The Windy City is no stranger to aviation, hosting two major international airports and smaller surrounding airports for private aircraft. Midway International Airport (MDW) is the smaller of the two commercial airports and primarily serves domestic destinations. MDW is home to one of Southwest Airlines’ largest crew bases and limited international service to Mexico and Canada. Modest in size, Midway is a fantastic travel option for those looking for excellent passenger facilities and a convenient travel experience on the south side of town.

The larger airport, and the one that we flew into, is O’Hare International Airport (ORD). O’Hare is a storied airport, the fourth busiest airport in the world in 2022, and featured in various media, such as Home Alone. ORD is connected to every corner of the United States and the world. From O’Hare, you can fly directly everywhere, from Addis Ababa and Auckland to Zihuatanejo and Zurich. This is thanks partly to the airport’s status as a hub for United Airlines and American Airlines and a focus city for Spirit Airlines. O’Hare is a truly impressive airport in terms of scale, with four terminals housing nine concourses with over 200 gates. I arrived at the C Concourse in the middle of the airfield and connected to the rest of the airport via an underground walkway. The C gates are relatively nice, featuring plenty of seating, charging ports and sockets, various shops and restaurants, and many restrooms. The terminal also has a United Club and a United Polaris Business Lounge.

My travel partner arrived at the L gates, and the walk between the two was over a kilometer (0.9 mi), or about 25 minutes. On the bright side, all domestic gates and some international departures are connected behind security, simplifying connections. However, the international terminal (which also services Delta, Southwest, and Frontier flights) is wholly separated and requires exiting security to connect. While the C gates were lovely because of recent renovation measures, the L gates were excellent because they are nearly new, opening only in 2018.

In addition to the in-terminal amenities for passengers, O’Hare has plenty of infrastructure that offers a smooth experience for all travelers. Hilton operates an onsite hotel, and an automated people mover system connects passengers between the domestic terminals, the international terminal, and the airport’s rental car facilities. Dozens of dining and retail options are scattered throughout the various concourses. You can buy LEGOs from a vending machine or hang out with a Brontosaurus skeleton. However, the most critical amenity for my travel partner and me on this trip was a direct metro connection to the city. It was quite a long walk from the gates to the station, but we eventually found our gateway into the city, the CTA Blue Line stop on the L.

Taking the L

One of the largest, oldest, and most iconic rapids transit systems in the United States, the Chicago “L” (coming from its primarily elevated nature) moves hundreds of thousands of passengers across its eight lines daily. Both Midway and O’Hare have convenient connections on the L to downtown. Midway is the southern terminus for the Orange Line, and O’Hare is the northern terminus for the Blue Line. The airports’ locations on the ends of the lines make it relatively easy for those unfamiliar with the system to find their way to the central business district. Chicago’s major rail stations are also within short walking distance of L stations, but there is no direct connection to the L within any of the three principal rail terminals.

The L station at O’Hare is located off of Terminal 2 underneath the airport’s large parking structure. It was easy to find thanks to plenty of wayfinding within the airport, and many ticket vending machines were available for travelers to purchase their fares. Trains from O’Hare into town are scheduled for every 10 minutes, though one common thread I’ve found with the CTA is that this is mostly just a figure on paper and does not reflect real-world practice.

The trains on the Blue Line, at least both times that I rode on them, felt like fairly old rolling stock. This is despite the trip into the city occurring on the newer 7000 series trains that began entering service for CTA in 2021. While the train had an updated exterior, the interior felt spartan and lacked many amenities that other modern systems have. This isn’t even just nice to have items like WiFi and charging ports but essential components such as present-position digital wayfinding and padded seats. One potential contributing factor is that L cars are smaller than most other rapid transit systems and more similar to those found on high-floor LRT systems due to the tight curves the trains traverse on elevated track sections.

The ride from O’Hare into town takes passengers through a variety of track alignments, transitioning quickly from underground to at-grade in highway medians to elevated sections crammed between buildings before diving back underground. While many L lines connect downtown on elevated tracks encircling the central business district (the famous Loop), the Blue and Red Lines arrive downtown via tunnels. The downtown stations are relatively small and austere. One thing the CTA could do better regarding passenger experience is seating. In stations, there is a noticeable absence of places to sit, and trains need to be better configured to provide enough seating for large numbers of passengers in many cases. The newer 7000 series trains have improved upon this last point, but there is still no room for luggage storage on trains, a significant problem considering the direct airport connection.

Fares for the L are decently priced, with a standard ride on the system costing $2.50. Rides from O’Hare are a flat $5 to anywhere in the system, be it to the other end of the line in Forest Park or one stop down in Rosemont. This is caused by a lack of fare zones, meaning that all trips are priced equally regardless of distance traveled. This fare difference for airport travelers means that, for most people, purchasing a 1-day (or even multi-day) pass makes sense instead of a single-ride ticket. Fares are paid via contactless tickets or reloadable fare cards called Ventura. The hardware works very well, and cards tap quicker than those on other systems I’ve ridden, such as BART and the Underground. However, a significant inconvenience arises from hardware, as all stations I encountered use standard turnstiles instead of more modern fare gates.

Station turnstiles cause significant issues for non-disabled travelers of a larger size, traveling with baggage or children. The more concerning problem with turnstiles is the increased complexity for those with limited mobility. There were multiple times during my few trips on the system that I saw non-disabled passengers struggling to get their baggage through the narrow turnstiles or down steep staircases; a lack of elevators and escalators in elevated stations means that some people with different mobility levels may not be able to access the platform.

The ride from O’Hare to downtown (specifically Washington/Madison Street station) took about 45 minutes. While the L has its fair share of issues, it works when it works. My travel partner and I got to where we needed to be for a fraction of the cost and time it would’ve taken to get a taxi or Uber.

A New Millennium (Park)

After exiting the L station at Washington/Madison, we found ourselves at the Richard Daley Center, the civic center for Chicago named after the former infamous mayor (no, not that one, his father). The center is located within the Loop and features a large fountain and a statue by Picasso. Millennium Park is a three-block walk to the east from the plaza. Along the way we passed a few more historic buildings, such as the Marshall Field and Company Building and the Chicago Cultural Center.

Millennium Park was designed near the turn of the millennium as a covering for a railroad yard and parking garage. The design provides vital infrastructure in the city's heart and more green space and public works. Millennium Park is technically part of the larger Grant Park, which has functioned as “Chicago’s Front Lawn” since it was first named a city park in 1844. The park has many public art installations and a world-recognized accessible design. Probably most famous for being home to the Bean (also known as Cloudgate, but Chicago has a knack for calling things by names it officially isn’t), Millennium Park has become one of the city's most recognizable and essential areas; it is a symbol of modern Chicago.

The Bean also happened to be my travel partner and I’s first actual stop in the city. No trip to Chicago is complete without stopping at the metallic legume. The surrounding plaza was filled with tourists from around the world trying their best to get a good photo of themselves with the sculpture. The day we visited was hectic, but seeing so many people enjoying the city and what it offers was beautiful. Being mad about many people at the Bean would be like going to New York and being upset that Time Square was filled with people or that Tower Bridge in London was full of tourists. People make cities for people; the community enjoying the space is what it was designed for and is the highest compliment to those that created it.

Another public space within Millennium Park is the Jay Pritzker Pavilion, a bandshell on steroids that is as much a work of art as a functioning entertainment complex. The pavilion houses the Grand Park Music Festival, the largest free classical music festival in the United States. The other significant public artwork is Crown Fountain, two large pillars with video boards displaying faces that sometimes “spit” water at those gathered below. The fountain is open to the public to walk through, meaning that dozens of children can cool off on a hot day in the water cascading from the towers. Millennium Park, and Grant Park, as a whole, have plenty more to offer. There is a pedestrian bridge that directly connects the park to the Art Institute of Chicago, Lurie Garden, and an ice rink in the winter. Typically we would have further explored the space in Grant Park to the south. However, much of the area was closed off during our visit due to the annual Lollapalooza Music Festival that Chicago hosts. Instead, we opted to walk to the shore.

Continuing east towards the lake, we eventually reached the Chicago Yacht Club and the path that connects various attractions along the waterfront. The shoreline of Lake Michigan is part of what makes Chicago such a unique city. While other cities like New York and Vancouver are based upon shorelines, no other metropolis matches Chicago in the scale of how vital the water is a part of the city. Chicago has 24 sand beaches on the freshwater lakefront. There are dozens of parks and trails scattering the lakeshore, such as the trail we took from the Yacht Club to the Museum Campus. Secluded from the car traffic of Lake Shore Drive by a row of trees and paralleling the harbor, the 1.9 km (1.2 mi) walk took us about 25 minutes to complete at a leisurely pace while offering us fantastic views of the harbor and open water that lies beyond. It was a beautiful day in the Windy City, so the trail was rather busy but never crowded due to its spacious design. At the trail's end is the Museum Campus, home to world-class facilities like the Field Museum, the Adler Planetarium, and the Shedd Aquarium, our eventual destination.

Before we went to the Aquarium, we had a stop to make first. Another must-do in the city is sampling one of the local delicacies. In this case, it was a Chicago-style hot dog. Traditionally, a Chicago-style dog as an all-beef frankfurter on a poppy seed bun with yellow mustard, white onions, sweet pickle relish, a dill pickle spear, tomato slices, celery salt, and pickled sport peppers. Ketchup is unacceptable on the Chicago dog, and ordering one with everything on it should still exclude the condiment. Most places require you to specifically ask for ketchup if they even offer it at all. The vendor we stopped at did offer it. Much to the dismay of the vendor and myself, my travel partner ordered hers with only ketchup. To compensate, the vendor refused to give her the hot dog until she danced. It was time to see the sea after eating a proper lunch (some more proper than others).

Under the C(hicago)

Shedd Aquarium is one of the forefront attractions in Chicago as one of the largest aquariums in the Western Hemisphere. Opened in 1930 as the first inland aquarium with a permanent saltwater fish collection, the iconic Neo-classical structure is just as impressive as its collection of sea life. The building and furnishings also play into the nautical theme, with sea turtles adorning the ceiling tiles and fish in the lamps.

Visiting the aquarium is highly recommended, but it is costly. A day ticket for non-Chicago residents starts in the upper $30’s when booked in advance. We paid just under $50 per person on the day of our visit. Additionally, you cannot purchase tickets at the facility unless paying with cash; if you purchase the day of with a bank card, you will be asked to buy the tickets on a personal device before entering the aquarium. Plan in advance as tickets are less expensive about a week out. Additionally, processing takes 15-20 minutes. Either for lingering covid restrictions, construction, or some other reason, all visitors enter the aquarium through the accessible entrance at the base of the museum. From there, you can either wait for the elevator to the lobby or walk through the field trip lunch room to the back staircase into the exhibit area.

Shedd has an awe-inspiring collection of animals and exhibits to explore. The entire facility, with a quick pass-through, takes over 3 hours to see the various exhibits. And that time is before considering stopping to read the information or explore a bit deeper. The aquarium offers a mobile app for visitors to dive deeper into the various creatures.

The exhibits display animals from around the world, including coral reefs, the Great Lakes, sharks, Beluga whales, Pacific White-sided dolphins, sea otters, rays, an anaconda, and millions of different fish. They range in size from tiny guppies to the impressive arapaima, the largest freshwater fish in the world (seriously, this thing is massive and also has lungs for breathing air). My favorite exhibit from Shedd was the Great Lake section, home to native species from the world's most extensive freshwater lake system, like sturgeon, pike, gar, bass, and even a monster alligator snapping turtle (which is technically non-native).

In addition to the exhibits, the aquarium has shows in the oceanarium. There are hands-on exhibit areas for petting stingrays, starfish, and sturgeon. In the lower levels there are play areas for children. The aquarium houses several dining options inside the facility, and plenty more vendors are outside too. And, of course, there is a large gift shop filled with nautical-themed items. No trip to a museum, zoo, aquarium, or other attraction is complete without a trip to the gift shop for a magnet and sticker.

Restricted Access

After several hours in Shedd, we departed the aquarium to head back to O’Hare for our flight home. We walked along much of the same route we followed to the aquarium, hugging the lakeshore and enjoying the views. Chicago has a unique skyline and list of attractions. Walking north, we had a better view of some of them, like the Sears Tower, the John Hancock Center, and Vista Tower (none of which are named that anymore). Chicago truly is one of the forefront locations for viewing modern architecture. One thing that we did not have time to do on this visit that I would like to do in the future would be to take an architecture-focused cruise along the Chicago River. We could also see portions of Navy Pier jutting into Lake Michigan, with the Ferris wheel and Chicago Children’s Museum primarily visible. Finally, because no trip is complete without it, we stopped for ice cream at one of the various vendors along the trail.

Eventually, we reached our station for the L, Monroe/Madison. When we arrived at the station, the digital wayfinding stated that a train was departing in one minute. Quickly making our way down the stairs from the street to the mezzanine to the platform, we soon found this was false. No worries, we thought; the video boards said another train was arriving in 3 minutes. That turned out to be wrong too. Ultimately we waited nearly 20 minutes for a train to arrive. By the time it did, the platform was packed with people, and so was the train. We crammed in as many as possible, and people were still waiting on the platform. The train was filled with people until we reached Damen station in Wicker Park.

Throughout my time riding public transit, the only other time I had experienced this level of crowdedness on a train was after hopping on the Piccadilly line after an Arsenal match. However, unlike the previous time when a major event ended while we were on the train, this was a regular service during rush hour on a weekday. CTA has been criticized by many residents and transit specialists alike due to its inconsistency, and I now completely understand why. Either a train had been taken out of service in the middle of rush hour, a significant operational event caused significant bunching, or the timetable they were quoting was false; to see such a poor level of service was shocking. Even in the middle of summer, Rush hour should see higher frequencies than over 20-minute headways.

While we had the pleasure of riding on the newer 7000 series trains from O’Hare into town on our previous journey, we were on one of the much older 3200 series train sets this time. While these cars are not the oldest rolling stock on the CTA or the Blue Line, they felt incredibly dated. The design was poor for maximizing either capacity or seating space. My travel partner and I could not get seats for much of the ride, finally being able to sit after nearly an hour on the train and longer on the platform upon reaching Harlem station, three stops from O’Hare. Our troubles did not end here, however. The train was stopped between Harlem and Cumberland for nearly an hour due to an unauthorized person walking along the tracks at Rosemont.

Ultimately this experience has left me to believe that the current operations and infrastructure for the CTA need to be improved, considering it serves the third largest city in the United States. Chicago has one of the lowest car ownership rates in the country, and thousands of people rely on the L to get to where they are going daily, whether it is residents trying to get to school or travelers visiting for a business meeting. The CTA has problems that cannot be attributed to only infrastructure or operations alone; both are components of the problem, along with management.

One of my most significant concerns with the L is the apparent need for serious and comprehensive modernization efforts. So far, most of their modernization has consisted of purchasing new train sets (though implementation has been sparse and execution questionable), digital wayfinding (which has been inaccurate), and sporadic track and station improvements. One way the L could improve reliability is not flashy and glamorous, but by enhancing their automation levels to compare with other systems worldwide. Improved signaling systems and realignments in sections could increase the frequency and speed at which trains run. Both of these scenarios, combined with platform screen doors, would help prevent the incident during my trip to the airport while improving headways and service reliability for those that rely on the CTA to get to where they need to be. The most pressing concern for the L is inaccessibility. One-third of stations on the Blue Line are inaccessible to wheelchair users and those with limited mobility. I am not an expert in how the L operates or what the CTA is doing, but from what I have seen, nearly any improvements to the lines that improve the reliability and efficiency of the system would be greatly welcomed.

After our train finally arrived at O’Hare, we went from over an hour and a half to just about a half hour to make it through security and to our gate. I very, very rarely run through airports. This was one of the few times that I did. Thankfully the lines for TSA were short that evening, with nearly no wait for the ID checking or screening process. O’Hare is used to moving large volumes of people, so finding and arriving at our gate was very simple. We arrived about five minutes before boarding.

Chicago is a dynamic city with elements that make it a must-visit for anyone interested in design. The city has some rough edges, and I found the public transportation system lacking, but it was an enjoyable visit nonetheless. We only saw a tiny portion of the city, and in future visits, I would love to see more, such as Lincoln Park, Navy Pier, and the Sears Tower observation deck. Partaking in more of the local culinary delights and music scene is also on my list of things to do. There is no perfect city, especially in all the various aspects that make urban life what it is; Chicago does some things incredibly well. Millennium Park is an icon and shining symbol of the city despite its relatively new status in a centuries-old city. The food, the music, the architecture, and the lake are all deeply infused in Chicago’s veins, and it was a joy to experience even a small part of it during the time that I was there.