Chicago: Out and Back in 12 hours
In an effort to take more trips but also save money, my sister and I have started doing out and back trips. We came across the idea of an out and back trip from the Instagrammer, Maddie Smith (@onthemovewithmad). The objective is to fly out to a city in the morning, hang out all day, and then fly back home that evening.
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Want more Chicago? Follow along on the vlog to see how I spent 12 hours in Chicago, Illinois.
Which Airport Should You Fly Into?
One of the most common questions first-time Chicago visitors ask is which airport to use, and for a one-day trip, the answer is almost always Midway (MDW). Here's why:
Midway (MDW) — Best for Day Trips
Primarily serves Southwest Airlines (great for cheap fares and flight deals)
The Orange Line L train gets you downtown in about 25–30 minutes for around $2.25
Smaller airport = faster security, easier navigation, less chaos
Less traffic congestion than O'Hare
O'Hare (ORD) — Better for International or Multi-Airline Options
Serves nearly every major airline (United, American, Delta, international carriers)
The Blue Line L train gets you downtown in about 50–60 minutes for $5
Much larger, busier, and easier to get turned around in
Rideshare to downtown runs around $40–50 vs. Midway's $25–35
My take: If you're flying Southwest (which often has the best deals), you're already flying into Midway. That's exactly what we did, and it worked perfectly for our 12-hour day trip. If the fare on another airline is significantly cheaper, don't stress, both airports connect to the L train and downtown is accessible from either.
Cost of the Trip
I subscribe to Going’s email service to be notified of cheap or mistake fares. Taking advantage of an email for a cheap flight and not spending money on a hotel, we could save money and visit more places. We chose Chicago for our first out and back trip because Southwest was having a $39/one way sale. So we could get a roundtrip plane ticket for less than $100. On top of that, the flight was under an hour and a half one way, so it wouldn’t cut too much into our time spent in the city.
We splurged and parked in the parking garage at the Nashville airport because there was a call for rain that evening. We also purchased a day CTA pass to use the Chicago public transportation system to get around to the different neighborhoods we wanted to visit.
Airfare - $77
BNA Parking Garage - $15 (we split in half)
1-day CTA pass - $5
Total Cost Per Person - $97
What to Pack
Since we did not have a homebase, such as a hotel, we had to pack light for our trip. We both brought a small backpack with us for the day trip. I love the Featherlight Backpack from Away for a daytrip. I packed a small amount of makeup and a hairbrush to touch up after the flight. There was a small chance of rain, so we packed an umbrella just in case. Since we knew that we wanted to hangout at the North Avenue Beach, I packed a small microfiber towel to either sit on the grass or sand as well as dry off if we got in the water. Lastly, I packed a portable power bank to charge my phone in case we were able to find an outlet while out and about sightseeing.
My biggest tip is be mindful of what you pack because you will be lugging it all day everywhere you go. After walking 30,000 steps that day, my backpack did start to feel pretty heavy.
Getting Around Chicago (CTA Tips)
Chicago's CTA (Chicago Transit Authority) makes day tripping incredibly easy, and it's exactly how we got around the whole day. Here's what you need to know:
The L Train Chicago's elevated train system (called "the L") runs eight color-coded lines. For a day trip focused on the downtown neighborhoods, you'll mostly be on the Red, Blue, Orange, and Brown lines.
Orange Line — Connects Midway Airport directly to the Loop (downtown). This is how you'll start your day.
Red Line — Runs from downtown north to neighborhoods like Lincoln Park, Old Town, and Lakeview (where Wrigley Field is). This is the most useful line for visitors.
Brown Line — A scenic loop through charming North Side neighborhoods.
How to Pay
1-Day Unlimited Pass ($5) — Perfect for a day trip. Unlimited rides for 24 hours, no tapping required every time you think about it.
Ventra Card — A reloadable card that works on both the L and buses. If you plan to visit again, it's worth grabbing one.
Ventra App — You can also use the app on your phone for contactless payment.
Tips for Riding the L
Google Maps works great for CTA navigation — it will give you real-time train directions.
Trains run frequently during peak hours (every 5–10 minutes) but can be less frequent on weekends in the evening.
Some platforms and stations require stairs — keep that in mind if you're overpacked.
The Red Line connects the most popular visitor neighborhoods; orient yourself around it.
Rideshare vs. Train For a budget-conscious day trip, the L train is the move. Rideshare from Midway to the Loop runs $25–35, whereas the train is about $2.25 one-way (or free with your day pass). Over the course of a day moving between neighborhoods, that adds up fast.
One Day Itinerary
Millenium Park
Morning
Fly out at 6:45am: Departed Nashville’s BNA airport and arrived at Chicago’s Midway airport at 8:15am. Purchased a day pass for the public transportation system.
Breakfast: Hopped on the the L and headed to the Lake View neighborhood. We passed by Wrigley Field on our way to enjoy a delicious breakfast at Cafe Tola.
Mid-Morning
Explored Lincoln Park: After breakfast, we got back on the L and made our way south to walk around Lincoln Park, where you can visit the Lincoln Park Conservatory and Lincoln Park Zoo (both free).
North Avenue Beach: Strolled along the “beach” at North Avenue Beach. We did not end up getting in the water, but I did pack a microfiber towel just in case I needed to dry off. Also, some kids had drawn a hopscotch game, so of course we had to take time out to play.
Lunch
Red Mango: Still feeling full from breakfast, we grabbed a smoothie at Red Mango and rested a bit while we charged our phones. I did bring a power bank, but it was nice to have a little rest anyway.
Afternoon
Millennium Park: After lunch, we strolled through Millennium Park. The Bean was under renovations, so there were barriers all around it making it a little bit difficulty to snap a picture.
Late Afternoon
Riverside Walk: Next we headed to the Riverwalk for a relaxing stroll along the water. I have previously done an architectural boat, but this trip was just sat on the grassy knoll and watch the boats float on by.
Evening
Dinner in River North: After enjoying the Chicago Skyline by the river, we were starting to get hungry. We had made reservations for dinner at Quartino, so we started walking to the River North neighborhood. We definitely had too much food…and too much wine. But it was so worth it.
Sunset at the Navy Pier: We ended our time in Chicago, walking the Navy Pier and watching the sunset behind the Chicago skyline.
Night
Fly home at 9:45pm: After a day full of walking and exploring, we boarded the L for the last time just as it started to rain. Luckily, we wouldn’t have to go back outside as we were headed to the Midway airport. We landed in Nashville 11pm exhausted from our fun filled daytrip.
A Quick Guide to Chicago's Neighborhoods
Chicago is very much a city of distinct neighborhoods, each with its own vibe. Here's a quick cheat sheet for day trippers:
The Loop — Chicago's downtown core. Home to iconic skyline views, the Riverwalk, Millennium Park, the Art Institute, and Willis Tower (Sears Tower to locals). Great for landmarks, not always where locals eat.
River North — Just north of the Loop, this is where you'll find some of the best restaurants in the city. It's walkable from Millennium Park and the Mag Mile. Our dinner at Quartino was in River North, and we'd go back in a heartbeat.
Lincoln Park — A beautiful, tree-lined neighborhood along the lakefront. Home to the Lincoln Park Zoo (free!), the Lincoln Park Conservatory, and North Avenue Beach. Very walkable and feels relaxed compared to downtown.
Lakeview / Wrigleyville — Home to Wrigley Field and a great brunch scene. Cafe Tola (where we ate breakfast) is in this neighborhood. If the Cubs are playing, the energy is electric — though the area gets packed.
Old Town — A historic neighborhood with a charming, walkable feel. Great for evening dining and drinks. Sits between Lincoln Park and River North.
West Loop / Fulton Market — This is where Chicago's best restaurant scene lives. If you're a foodie, make the time to explore here. It's a bit further from the tourist track but absolutely worth it.
Wicker Park — An artsy, indie neighborhood with great vintage shops, local coffee, and a vibrant bar scene. Fun for an afternoon wander if you want something off the tourist path.
The Bean in Millennium Park
Everything I Wish I'd Known Before My Chicago Day Trip
Book dinner early. Popular River North and West Loop spots fill up fast. Make an OpenTable or Resy reservation at least a few days in advance (or weeks ahead in summer).
The Bean might be under renovations. Millennium Park is a must, but if you're going specifically for the Bean (Cloud Gate), check in advance whether it's accessible. It was surrounded by barriers when we visited and took some creative angling to photograph.
Give yourself 20–30 minutes to get from Midway to downtown. The Orange Line is fast and efficient, but factor transit time into your itinerary from the moment you land.
Chicago is a walking city in some areas. The downtown lakefront, Millennium Park, the Riverwalk, and Lincoln Park are all very walkable. But the neighborhoods are spread out, so you'll rely on the L to hop between them. We walked 30,000 steps, so comfortable shoes are non-negotiable.
Deep dish takes time. If you want real deep dish (not by the slice), most places need 45 minutes to bake it. Plan it as your last meal of the day or make a reservation.
The Riverwalk is free. People pay a lot for architecture boat tours (worth it if you have time), but just walking the Riverwalk and sitting on the grassy knoll with a view of the city is completely free and genuinely stunning.
Safety basics: Like any major city, stay aware of your surroundings, especially on public transit. Keep your belongings secure. The neighborhoods most visitors frequent, Loop, River North, Lincoln Park, Old Town, Lakeview, are all very safe. Stick to well-lit, busy areas in the evening.
Download the apps: Google Maps (CTA navigation), Ventra (transit payment), and OpenTable or Resy (dinner reservations).
The Chicago Architecture Boat Tour is worth it on a longer trip. We didn't do it this time, but it's consistently ranked as one of the best things to do in Chicago by locals and visitors alike. The Chicago Architecture Center leads the original version, and seeing the skyline from the river is unreal.
Navy Pier Ferris Wheel
Final Thoughts
We spent over 12 hours in Chicago and walked over 30,000 steps! It was definitely a fun experience to hang out in Chicago for the day. My sister and I are already planning our next out and back trip. Leave a comment below if you found this helpful.
Ciao for now!
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