Look, if you’ve just finished boot camp or you’re visiting a recruit for liberty, the last thing you want to do is stare at a confusing transit map for an hour. You’re tired. You’re excited. You just want to see the skyline. The trip from Great Lakes Naval Base to Chicago is basically a rite of passage for every sailor who passes through North Chicago, but it can be a total headache if you don’t know the rhythm of the Metra or the reality of the Kennedy Expressway.
It's about 35 miles. That sounds short. It isn’t. Depending on how you play your cards, that 35-mile stretch can take forty-five minutes or two hours of your life that you'll never get back.
The Metra Union Pacific North Line is Your Best Friend
Honestly, don't drive. Just don't. Unless you have a specific reason to have a car on base, the Metra is the undisputed king of this route. The Great Lakes station is literally right there, sits right outside the main gate, and drops you off at Ogilvie Transportation Center in the heart of the Loop.
The UP-N line is reliable. It’s also where you’ll see dozens of other sailors in their dress whites or blues, all looking for the same thing: a decent burger and a glimpse of Lake Michigan from a different angle. If you’re traveling on a weekend, the Metra "Day Pass" or "Weekend Pass" is the greatest deal in the history of Illinois transit. For a flat fee—usually around ten bucks for the whole weekend—you get unlimited rides. Compare that to an Uber that might cost you $70 one way during peak hours, and the choice is pretty obvious.
One thing people get wrong is the schedule. This isn't the NYC subway; the trains don't come every five minutes. On weekdays, you have plenty of options, but on Sundays? You might be waiting over an hour if you miss your ride. Always, always download the Ventra app. It’s the only way to track the trains in real-time. If the train says it's departing at 10:14, it is departing at 10:14. These conductors don't wait for "one last person" running across the parking lot.
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Driving Down the I-94 Nightmare
If you absolutely must drive from Great Lakes Naval Base to Chicago, prepare your soul for the Edens Expressway.
Traffic in Chicago is a living, breathing entity that hates you. If you leave the base at 07:00 on a Tuesday, you are walking into a buzzsaw of commuters. The merge where I-94 and I-294 meet is a notorious bottleneck. You'll see locals weaving through lanes like they're in a Fast & Furious sequel, but my advice is to just stay in the center lane and accept your fate.
Parking is the second boss fight. If you’re heading to Navy Pier or the Magnificent Mile, you’re going to pay a "tourist tax" in the form of $40-$60 parking garages. Use SpotHero. I cannot stress this enough. If you don't use a parking app to pre-pay for a spot in a garage, you are essentially throwing money into a bonfire. There is very little "easy" street parking in the parts of Chicago you actually want to visit.
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A Quick Note on "Liberty" Rules
For the sailors: check your Liberty Policy. Every command has different rules about how far you can go and what time you have to be back. Chicago is well within the "radius" for most, but the commute time can sneak up on you. If the Metra breaks down—which happens rarely but isn't impossible—you need a backup plan. Always have a rideshare app ready as a "break glass in case of emergency" option to get back to base before your liberty expires. Missing movement or being UA because of a train delay is a conversation you don't want to have with your Chief.
What to Actually Do Once You Get to the City
Most people get off the train at Ogilvie and just start walking east. That’s fine, but Chicago is huge. If it's your first time, you’re probably heading for the "Bean" (Cloud Gate) in Millennium Park. It’s a bit of a walk from the station, about 15-20 minutes, but it's a straight shot down Madison Street.
If you're looking for food that isn't base food, Chicago is a literal gold mine.
- Deep Dish: Lou Malnati's or Giordano's. Don't ask which is better; it's a civil war in this city. Just pick one.
- Italian Beef: Go to Al's or Portillo's. Ask for it "dipped" if you want the real experience.
- The Museums: The Art Institute is world-class, but the Museum of Science and Industry is further south and actually has a real German U-505 submarine. For a Navy person, that’s usually the highlight of the trip.
One thing people overlook is the Riverwalk. It’s been renovated massively over the last few years. You can walk along the Chicago River, grab a coffee, and watch the architectural boat tours go by. It’s way more chill than the chaos of Navy Pier.
The "Secret" Alternative: The Pace Bus
Not many people talk about the bus system, but Pace Bus 606 and others serve the suburban areas around Great Lakes. It’s slower. It’s less "scenic." But if the trains are undergoing maintenance or there’s a massive strike (rare, but it happens), the bus system can get you to the Blue Line or Purple Line of the "L" train system.
The Purple Line in Evanston is actually a really cool way to see the North Side. You take the Metra to Evanston (Davis Street station), hop on the Purple Line, and you can ride that into the city. It gives you a much better view of the neighborhoods than the Metra, which mostly runs through industrial corridors and backyards.
Weather Realities
Chicago weather is no joke. The "Windy City" nickname actually refers to the politicians, but the wind off Lake Michigan will still bite your face off in February. If you’re traveling from Great Lakes Naval Base to Chicago between November and March, dress in layers. The train will be roasting hot, and the platform will be a freezer. You'll see recruits in their heavy bridge coats looking sharp, but make sure you have gloves. Standing on that elevated platform at Great Lakes with a 20mph wind coming off the water is a special kind of cold.
Navigating the Return Trip
The most stressful part of the whole day is getting back. The last Metra trains leaving Chicago for Great Lakes usually depart around midnight on weekends, but you need to check the specific "Outbound" schedule for the UP-N line.
Ogilvie Transportation Center is a big place. Don't show up two minutes before the train leaves. You need time to find the right platform, buy your ticket (if you didn't use the app), and grab a Garrett Popcorn for the ride back. The "Great Lakes" stop is very specific—don't get off at Waukegan or Lake Bluff by mistake. They look similar in the dark when you're tired, but you'll end up with a very expensive Uber bill to get back to the gate.
Real Talk: Safety and Awareness
Chicago is a major city. Like any major city, stay aware. The area around the train stations and the main tourist spots is generally very safe and heavily patrolled, especially by Transit Police and CPD. However, if you're in uniform, you’re a magnet for attention—mostly good, but sometimes people will try to sell you things or ask for money. Just keep moving. Stay with your group. The "Buddy System" isn't just a Navy rule; it’s just common sense in the city.
Actionable Steps for a Successful Trip
- Download the Ventra App: This is non-negotiable. It handles your tickets and your timing.
- Pack a Power Bank: Your phone will die from taking photos of the skyline and checking GPS. You don't want to be at Ogilvie with a dead phone trying to find your train platform.
- Check the Cubs/Sox Schedule: If there’s a home game, the trains and the city will be twice as crowded. Plan for extra travel time.
- Stay North of I-55: Unless you have a specific destination like the Museum of Science and Industry, most of your "first-timer" Chicago highlights are in the Loop, River North, or Lincoln Park.
- Keep Your ID Handy: You'll need it for base entry, obviously, but many Chicago attractions offer military discounts that aren't always advertised. Ask at the ticket counter.
The trip from the base to the city is a vital part of the Great Lakes experience. It’s your chance to breathe, eat something that didn't come from a galley, and remember why you’re doing what you’re doing. Just watch the clock—Chief doesn't care how cool the Bean looked if you're late for muster.