Heading Out Of Town? Here’s Your Chicago Holiday Travel Survival Guide

CHICAGO — It’s officially holiday travel season — which means it’s also officially travel stress season.

More than 1.65 million people are expected to travel through O’Hare and Midway airports between Tuesday and Nov. 27 for Thanksgiving, with this Sunday expected to be the busiest travel day, according to the Chicago Department of Aviation.

The roads and trains will be busy, too.

Block Club has tips so you can get ready to hit the road, rails or air with a whole slew of other Chicagoans headed for family visits and vacations — and use this survival guide to manage every step of the process.

Packing Clothes And Snacks

Your packing list should really be dictated by the type of travel you are undertaking.

For clothing, it’s a good idea to start watching the weather in your intended destination about a week before leaving. That way, it’ll be pretty obvious what type of clothes to pack and how much. If you’re going somewhere within the United States, you can check the forecast on the National Weather Service site. For international travel, you can look at a weather agency in your destination or look at Accuweather.

You can save space in your bag by rolling your clothes — though they might end up more wrinkled, if that’s important to you. Something to consider is if your destination will have laundry services, because then you can bring fewer clothes to save space and wash them while you’re there.

And don’t forget a bathing suit if the holiday trip is to somewhere warm and coastal.

Airport

If you’re flying, go online or call your airline to ask about the baggage rules for your flight — if you’ve got a short trip, you might be fine with just traveling with a backpack, which many airlines allow on as your free “personal item.”

But pay attention to how big your bag gets as you pack: Some carriers are sticklers for bag size, and you don’t want to be told at the gate that you need to check your bag and pay a fee because it’s too big.

You can search TSA’s website to figure out what can — and can’t — go through security with you. This is particularly helpful for personal care items where you’re not sure if they’re considered a liquid.

Full water bottles are not allowed through airport security, so remember to leave those at home or empty any reusable bottles prior to arriving at the airport.

For plane travel, it can also be helpful to bring snacks in a carry-on in case no food is served during the flight. But pack as light as possible, as well — dragging around a ton of luggage is generally a pain, especially when airlines charge fees for checked bags.

Driving, Trains

Driving and taking the train have much looser rules in terms of what you can bring. Two suitcases? No problem. Full bottles of water and a dozen doughnuts? That’s all right, too. Bring what’s necessary for a comfortable ride without going overboard.

How To Get To The Airport

Getting to either of Chicago’s major airport is easier than it seems.

Driving

For drivers, O’Hare is situated right off I-190, and signs pointing out the path to the airport are large and visible on I-90 and I-294. There are numerous parking options around the airport, including in lots where you can take a shuttle to the airport terminal you need.

Midway Airport is on South Cicero Avenue. You can take I-55 to the Cicero Avenue South exit and follow the road right to it.

You can park at the airports, but be prepared to be hit with fees — and spots will fill up quickly during holiday travel, according to the aviation department.

You can check the status of O’Hare parking lots online before you leave to make sure you’ll be able to snag a spot, or you can even reserve a spot beforehand. You can do the same for Midway’s lots.

If you’re getting dropped off, your driver can leave you at a Kiss n’ Fly spot. O’Hare’s is at the Multi-Modal Facility at 10255 W. Zemke Blvd., and Midway’s is at West 59th Street and South Kilpatrick Avenue.

If you’re getting picked up, your driver can wait in a cellphone lot, which are free at Midway and O’Hare. O’Hare’s cellphone lot is at 560 N. Bessie Coleman Drive, and Midway’s is at West 61st Street and Cicero Avenue.

Taxis and ride-shares go to both airports, but it can be expensive depending on the origination point — and you’ll need to hope a driver is available to take you, which could be tricky if you’re traveling early or late in the day.

CTA

Those taking public transportation can get to O’Hare on the Blue Line, which heads directly into the airport.

The Orange Line connects travelers to Midway.

Metra

You can also get to O’Hare by taking Metra’s North Central line between Union Station and the O’Hare Transfer station.

And Don’t Forget …

Before heading out for any flight, it’s important to triple check the departure airport. Having two in Chicago can be confusing, but they’re easily distinguished by their codes: ORD for O’Hare and MDW for Midway.

And remember to arrive at least three hours early, especially with the rush of holiday travel hitting both airports. Getting through security will take a while with the crowds, and you don’t want to miss your flight.

You can get an idea of checkpoint times at O’Hare online.

To Check Bags Or Not to Check Bags

Scores of checked bags were lost all around the country as flight complications from Southwest Airlines put a hitch in holiday travel last December.

In fact, last year was one of the worst years for lost luggage: The BBC reported this August that 26 million pieces of luggage went missing in 2022. But new data shows the situation is improving.

While the idea of checking bags may inspire fear or skepticism, it’s probably not as bad (anymore) as people say. That being said, it’s always easiest to travel carry-on-only for single-leg flights if there are important items in the luggage. Try to pack light and it won’t be an issue.

How To Stay Entertained Or Find Food at the Airport

For the hyper-organized, O’Hare and Midway have maps of what to find in the airport. It’s easy to plan activities — and meals — in advance by looking at the sites, which separate out restaurants, shopping, services, and amenities by area of the airport.

For those who prefer to fly by the seat of their pants, each airport has maps inside showing travelers what’s in each section of each airport.

Families with kids can go to O’Hare’s family lounge, which offers an area where toddlers and other young kids can play, as well as stroller parking.

Both airports also have nursing rooms for people who are breastfeeding or chestfeeding babies. There’s a nursing room in Concourse C and a nursing pod at Gate A5 in Concourse A, and O’Hare has options, as well.

Making The Most Of A Road Trip

If you’re driving, expect a lot of time on the road — construction on the Kennedy and elsewhere continues, and traffic has been abysmal.

On the plus side, that means it’s time to bring out the car games! Road trips can be tons of fun, but it’s important to add in ways to break up the monotony of the road.

License Plate Bingo is one that can last the whole trip — try to find a license plate from every state.

Padiddle is another good one. You keep track of who counts the most cars with a headlight out, and the person with the highest number at the end of the trip wins.

And don’t forget to take breaks to avoid highway hypnosis and keep senses alert. Driving-Tests, a site for researching before a DMV test, suggests taking a break every two hours.

How To Use Amtrak And Metra

In Chicago, long-distance train travel means taking the Metra or Amtrak.

Metra is the commuter line, meaning it heads out into the suburbs, and it has one stop into Wisconsin.

Amtrak is interstate and can take riders across the country.

Metra stops are available Downtown at Union and Ogilvie Stations and in a few spots around the city, while Amtrak boards only at Union Station. To figure out the best train for holiday travel, look online at the schedules and time tables to see what’s best, and buy tickets in advance. Especially with Amtrak, some routes sell out pretty quickly for holiday travel.

If you’ve got an overnight journey and a few more bucks for comfort, you can see if your Amtrak train offers cabins with bunks. The beds are tiny, but they’re better than sitting straight up.

Amtrak trains for long journeys also offer dining options, though you can bring food and drinks on board to save a bit of money.

And even if you’re taking the train, plan to get to your station with time to spare: You don’t want to be running after a train as it leaves the station.

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