I’ve made this trip more times than I can count. Work, kids, concerts, a Cubs game, you name it. So here’s my honest take, with real trips that went great…and a couple that were not so great.
Need more granular numbers, mile-by-mile exit notes, and the exact spot where the scenery flips from cornfields to Chicago skyline? I laid all of that out right here so you can bookmark it for later.
The short answer
- By car: about 180 miles. It takes 3 to 3.5 hours in normal traffic.
- Straight line: about 165 miles. (Birds fly faster than my Subaru.)
- By train: around 5 hours on Amtrak, give or take.
- By bus: usually 4 to 5 hours, depending on stops.
- By plane: 1-hour flight, but about 3 hours door-to-door when you count the airport stuff.
Time zones matter. Indianapolis is Eastern. Chicago is Central. Heading to Chicago, you “gain” an hour. Coming back, you “lose” one. Sneaky clock.
My real drives (good, bad, and windy)
I drive a 2018 Subaru Outback. Nothing fancy, just sturdy. I take I-65 almost the whole way. It’s simple: point north and go.
- Best time for me: Monday morning, wheels up at 7 a.m. I reached downtown Chicago in 3 hours flat. Light wind, smooth road, zero drama.
- Worst time: Friday at 3 p.m. in July. Road work near Gary plus a crash. It took 4 hours and 40 minutes. I was fine, but my iced coffee gave up halfway.
- Windy day story: One March trip felt like my car was a kite. I kept a steady 65 mph and both hands on the wheel. Got there safe. Just tired.
Gas? I usually stop once. Fair Oaks Farms (off I-65) is my go-to. Clean bathrooms, good snacks, and a latte that doesn’t taste like sadness.
Toll note: If you take the Chicago Skyway (I-90) at the end, there’s a toll. I use I-PASS, but E-ZPass works too. You can avoid it by staying on I-94, but it’s slower.
Train days: slow, calm, and kind of nice
I’ve taken the Amtrak Cardinal from Indianapolis to Chicago on a rainy Sunday. It took just under 5 hours. I read, I snacked, I stared out the window like a thoughtful movie character. It was calm. Not fast, but calm.
- I paid around $35 for my ticket.
- The seat was comfy, and the power outlet worked.
- We rolled into Union Station, which is an easy walk to a lot of stuff.
If you like peace and don’t need speed, train days can be lovely. And if you want my blow-by-blow of a recent sleepy, snack-filled ride, you can check out the full story here.
Bus runs and quick flights
Bus: I’ve used FlixBus and Greyhound. Prices were friendly (I paid $22 once), but timing was a little wobbly. My last bus took about 4.5 hours with a quick stop. Bring a hoodie. Bus AC hits different.
Flight: I’ve flown IND to ORD and IND to MDW. If you want the exact mileage between the airports, this IND-to-ORD distance calculator breaks it down in one click. The flight itself is an hour, but door-to-door took me about 3 hours with parking and security. TSA PreCheck helped. If you’re heading right downtown, Midway (MDW) felt easier than O’Hare (ORD).
Tiny tips that save big time
- Leave early or late. Middle of the afternoon can get sticky near the state line.
- Check traffic near Gary and the Skyway. That spot loves a slowdown.
- Watch the wind. I-65 is open and gusty. Keep a steady pace.
- Snacks and fuel: Fair Oaks Farms is a winner; Love’s and Pilot are fine too.
- Winter rule: keep a blanket and gloves in the trunk. Learned that the hard way.
Before any long drive, I like to skim the travel safety guides over at ALCO — their checklists are quick, free, and have twice reminded me to top off tire pressure before hitting I-65.
What I actually do
- Quick work trip? I drive. I leave by 7 a.m., set Google Maps, and hit I-65.
- Rainy weekend? Train. I bring a book and headphones.
- Tight schedule with meetings? I might fly into Midway and take the Orange Line.
Money talk (real numbers I paid)
- Gas for the round trip in my Subaru: about $35 to $45, depending on prices.
- Train: $30 to $50 for a basic ticket.
- Bus: $20 to $40 most days.
- Flight: I’ve paid anywhere from $98 to $220, not counting bags.
PS: If your itinerary turns into an overnight on the Indy side, I road-tested four different boutique stays and shared the unfiltered pros and cons in this roundup.
One quirky side note: if your trip winds up as a solo evening in either city and you’re curious about discreet ways to line up a last-minute dinner date, you might want to read this refreshingly candid Ashley Madison review—it breaks down membership costs, privacy safeguards, and real-world success odds so you can decide whether the app is worth a download before room-service arrives.
If your travels ever push you beyond the Midwest—say you’ve got a connecting flight through Newark or a conference on the East Coast—you might also appreciate this straightforward Doublelist Newark guide that explains how locals use the platform, the best times to post, and safety tips so you can navigate the city’s casual-meetup scene with confidence instead of guesswork.
So…how far is it, really?
It’s close enough to feel easy, but far enough to plan a little. I call it a 3-hour drive that sometimes turns into 4. I’ve done it fresh at sunrise and grumpy after work. Both were fine. You know what? With coffee, a good playlist, and a decent plan, the miles go fast.
If you need simple: Indianapolis to Chicago is roughly 180 miles. Car: about 3 hours. Train: about 5. Bus: about 4 to 5. Plane: 1 in the air, 3 total.
See you on I-65. I’ll be the one singing along and watching the clouds.