Chicago Luggage Travel Guide: Pack Smarter for O’Hare & Midway

By All Star Limo Team
September 1, 2026 • 12 min read

This Chicago luggage travel guide helps passengers prepare for trips through O’Hare International Airport (ORD) and Midway International Airport (MDW), from carry-on rules and checked baggage to choosing a vehicle with enough room for suitcases, strollers, golf clubs, business equipment, and group travel.

Luggage can change an airport transportation plan faster than passenger count. Three travelers with carry-ons are one type of trip; three travelers with six checked bags, golf clubs, and a stroller are another. When booking a Chicago limo service, sharing the complete passenger and baggage count helps ensure the vehicle matches the trip before departure day.

Quick answer: Choose your airport vehicle based on people and luggage together. All Star Limo Service currently lists the Cadillac Escalade, Lincoln Navigator, and Chevrolet Suburban at up to 6 passengers and 4 pieces of luggage, while the Mercedes-Benz S-Class is listed at 3 passengers and 2 bags. Sprinter configurations provide more room for larger groups, with current All Star listings showing models accommodating up to 14 passengers with additional luggage capacity. Bag size, strollers, golf equipment, and oversized items can change the real-world fit, so disclose them when reserving.

Chicago Luggage Travel Guide: Count More Than Suitcases

When someone says, “We have four bags,” that does not always describe the actual load.

An airport trip can include:

• checked suitcases;
• carry-on rollers;
• backpacks;
• laptop bags;
• garment bags;
• purses and personal items;
• strollers;
• car seats;
• golf clubs;
• sports equipment;
• mobility equipment;
• musical instruments;
• trade-show cases;
• and oversized luggage.

A vehicle may have enough seats without having enough comfortable cargo space.

Consider two groups:

Group A

• 4 passengers
• 3 standard suitcases
• 2 backpacks

Group B

• 4 passengers
• 6 large suitcases
• 2 carry-ons
• stroller
• golf bag

The passenger count is identical.

The transportation requirement is not.

That is why All Star’s current fleet information publishes both passenger and luggage capacity rather than only seating numbers.

Check Your Airline Rules Before You Pack

O’Hare (ORD) and Midway (MDW) serve many airlines, and baggage policies are determined by the airline rather than the airport.

Before leaving home, confirm:

• carry-on dimensions;
• personal-item limits;
• checked-bag allowances;
• checked-bag weight limits;
• oversized-baggage fees;
• overweight charges;
• sports-equipment policies;
• stroller and child-seat rules;
• musical-instrument policies;
• and international baggage allowances.

A traveler who flew through Chicago last month should not assume the same rules apply to a different airline, ticket class, or international itinerary.

The safest approach is to verify baggage limits directly with the operating airline before packing.

TSA Rules That Affect Your Carry-On

Airline rules determine the size and number of bags.

TSA rules determine what can pass through security.

For standard carry-on liquids, TSA generally follows the 3-1-1 rule: containers of 3.4 ounces or 100 milliliters or less placed within the permitted liquids bag. Exceptions can apply to certain medically necessary items and other special circumstances.

If you are uncertain about a particular item, use TSA’s official What Can I Bring? tool rather than relying on an old packing list or social-media post.

Keep Essential Items Accessible

Consider keeping these in a personal bag:

• passport or ID;
• medication;
• wallet;
• phone;
• keys;
• laptop or tablet;
• important travel documents;
• valuables;
• and anything you would have difficulty replacing during the trip.

This is useful not only at security but during the airport ride.

You do not want to unload several large suitcases at O’Hare (ORD) because a passport or medication ended up at the bottom of the wrong bag.

Power Banks Belong in Your Carry-On

The FAA specifically requires spare lithium batteries and power banks to remain in carry-on baggage, not checked baggage.

If your carry-on is taken at the gate and checked, spare lithium batteries and power banks should be removed and kept with you in the aircraft cabin. The FAA currently allows most rechargeable batteries up to 100 Wh, while batteries between 101 and 160 Wh generally require airline approval; batteries exceeding 160 Wh are generally prohibited on passenger aircraft.

Travelers should still check their airline because carriers may impose stricter rules.

The official FAA guidance is available through PackSafe lithium battery information.

What About Smart Luggage?

Smart bags with built-in lithium batteries deserve extra attention.

FAA guidance says lithium-battery-equipped baggage generally must remain carry-on luggage unless the battery can be removed. If the bag is checked, applicable removable batteries must travel according to the rules for spare batteries.

That is worth checking before arriving at security.

Chicago Luggage Travel Guide for O’Hare (ORD) Arrivals

O’Hare is especially important for international travelers because baggage handling can add considerable time between landing and being ready for transportation.

For passengers entering the United States at O’Hare (ORD), the airport explains that travelers clear primary immigration inspection and then claim their baggage before proceeding through customs and agriculture screening — even when the bag has been tagged through to another destination.

That means:

aircraft landed does not mean passenger is ready for pickup.

An international passenger may still need to:

1. leave the aircraft;
2. walk through the international arrival process;
3. clear immigration;
4. claim checked baggage;
5. complete customs/agriculture procedures;
6. recheck bags when connecting;
7. and reach the transportation meeting point.

For airport arrivals, All Star’s O’Hare Limo Service includes real-time flight tracking and coordinated airport pickup.

O’Hare Has Luggage Porters

This can be useful for passengers arriving with several large pieces.

O’Hare states that luggage porters are available in the international baggage-claim area to assist travelers transporting their luggage.

For international families, older travelers, or passengers arriving with many bags, that is worth knowing before landing.

Chicago Luggage Travel Guide for Midway (MDW)

Midway (MDW) is more compact than O’Hare, but the same luggage principle applies: collect everything first and make sure your transportation plan matches what actually came off the aircraft.

All Star’s Midway Limo Service provides private MDW pickups and drop-offs with sedans, SUVs, Escalades, S-Class vehicles, and Sprinter vans.

Midway states that arriving passengers are picked up from the lower-level outermost curb, and curbside waiting by vehicles is prohibited.

For the passenger, that means it is better to finish collecting luggage and follow the confirmed pickup instructions rather than rushing outside before everyone and every bag is ready.

If Your Checked Bag Does Not Arrive

A missing airline bag and an item lost somewhere in the terminal are two different problems.

At both O’Hare and Midway, items left near ticket counters, gates, or aboard an aircraft generally need to be handled through the airline. Items lost at TSA checkpoints go through TSA Lost and Found, while other airport areas may be handled by airport-specific departments.

If your checked suitcase never appears on the carousel:

contact your airline first.

If you already have a chauffeur waiting, also let the transportation company know you are delayed at baggage claim.

Useful information includes:

• airline;
• flight number;
• baggage claim location;
• approximate delay;
• and a reachable mobile number.

That gives the chauffeur and dispatch team useful information instead of leaving them to estimate what happened.

How Much Luggage Fits in an All Star Luxury SUV?

This is where choosing the right vehicle becomes important.

All Star’s current Chicago limo fleet includes late-model sedans, SUVs, luxury vehicles, and Sprinter vans.

Current published examples include:

• Cadillac Escalade: 6 passengers / 4 luggage
• Lincoln Navigator: 6 passengers / 4 luggage
• Chevrolet Suburban: 6 passengers / 4 luggage
• Mercedes-Benz S-Class: 3 passengers / 2 luggage

These numbers are planning guides.

A standard suitcase is not the same shape as:

• golf clubs;
• an oversized international bag;
• stroller;
• wheelchair;
• trade-show case;
• photography equipment;
• or several large hard-shell suitcases.

Tell dispatch what is actually traveling.

Why an Escalade Can Be Worth the Upgrade

A sedan may be perfect for one or two travelers with light luggage.

But the calculation changes when passengers want more room.

Compared with All Star’s current Mercedes S-Class listing at 3 passengers and 2 pieces of luggage, the Cadillac Escalade is listed at up to 6 passengers and 4 pieces of luggage.

That makes the Escalade attractive for travelers who want:

• additional passenger capacity;
• more luggage flexibility than an executive sedan;
• a larger premium cabin;
• easier family travel;
• a luxury SUV experience;
• and extra flexibility for longer airport trips.

The Escalade may cost more than a standard vehicle depending on the trip, but price is not the only consideration.

For some travelers, the upgrade is worthwhile because it provides a better combination of space, comfort, privacy, and presentation.

That is especially true after a long flight when passengers have several pieces of baggage and still need to travel from O’Hare (ORD) or Midway (MDW) to Chicago or the suburbs.

Do Not Treat Maximum Capacity as a Packing Challenge

If a vehicle is listed for six passengers, that does not mean six adults with several large suitcases each will automatically fit comfortably.

A more useful question is:

How close are we to the passenger limit AND the luggage limit?

If both are near maximum, discuss the trip before booking.

A larger vehicle may make the airport transfer considerably more comfortable.

Families Need More Cargo Space Than They Think

Family luggage is rarely just suitcases.

A family trip may include:

• stroller;
• car seat;
• diaper bag;
• children’s backpacks;
• carry-ons;
• checked luggage;
• blankets;
• snacks;
• mobility items;
• and personal bags.

When reserving, do not describe that trip as:

“Four people and four suitcases.”

Tell the company about the stroller and other bulky pieces too.

They take up real cargo space.

Golf Clubs Change the Vehicle Decision

Chicago travelers heading to golf trips or arriving with golf equipment should count each golf bag separately.

Golf bags are long and bulky, and their shape can reduce how ordinary suitcases can be arranged around them.

For example:

3 passengers + 3 suitcases

is very different from:

3 passengers + 3 suitcases + 3 golf bags

That second trip may justify moving from a sedan to an SUV or from an SUV to a larger group vehicle.

Business Travelers Have Different “Luggage”

Corporate travelers may carry far more than conventional suitcases.

A group arriving for a conference or meeting may have:

• laptop bags;
• garment bags;
• presentation equipment;
• samples;
• printed materials;
• event displays;
• and trade-show cases.

That equipment should be included in the capacity conversation.

If a team has eight people but also eight checked bags and business equipment, seat count alone does not tell you which vehicle to reserve.

Chicago Luggage Travel Guide: When a Sprinter Makes More Sense

When the group becomes larger, trying to force everything into SUVs may create unnecessary complications.

All Star’s Chicago Sprinter Limo Service is designed for larger airport, corporate, family, and event groups.

The current site describes Sprinter configurations for approximately 10–14 passengers, with additional luggage capacity for airport trips.

A Sprinter can make sense when:

• several passengers are on the same flight;
• most travelers have checked luggage;
• the group has golf or sports equipment;
• a corporate team has presentation materials;
• family members want to remain together;
• or splitting bags and passengers among several vehicles would complicate the trip.

One Sprinter or Two SUVs?

There is no universal answer.

One Sprinter may work better when:

• everyone shares one pickup;
• everyone takes the same flight;
• the destination is the same;
• there are many suitcases;
• and keeping the group together matters.

Two SUVs may be better when:

• passengers start in different locations;
• travelers need different drop-offs;
• executive privacy matters;
• schedules differ;
• or the group will split after arriving in Chicago.

Choose around the itinerary — not only the passenger number.

Airport Drop-Offs: Solve the Luggage Problem at Home

The best time to determine whether the luggage fits is before the chauffeur arrives.

For airport departures, give the reservation team:

Passenger count
Adults and children.

Checked bags
Full-size suitcases.

Carry-ons
Cabin rollers and similar bags.

Special items
Strollers, golf clubs, car seats, equipment cases, mobility devices.

Flight information
Airline, flight number, airport, and departure time.

Pickup location
Home, office, hotel, or another address.

All Star’s Chicago Airport Limo Service handles scheduled pickups and drop-offs for O’Hare (ORD), Midway (MDW), and other Chicago-area airports with flight tracking and multiple vehicle classes.

The more accurate the information, the easier it is to assign the appropriate vehicle.

Update the Reservation If Your Packing Changes

Airport transportation is often booked before anyone has actually packed.

That creates a common situation:

Reservation day:
3 travelers + 3 bags

Travel day:
3 travelers + 6 bags + stroller + golf clubs

That is no longer the same transportation request.

If your luggage count changes substantially, update the company before pickup.

A short call can prevent a last-minute vehicle change.

When Meet & Greet Helps With Heavy Luggage

For some arrivals, curbside pickup is enough.

For others, especially international passengers or travelers handling multiple bags, in-terminal assistance can simplify the transition from baggage claim to the vehicle.

All Star’s Chicago Meet & Greet Service includes an inside-terminal greeting, flight tracking, luggage assistance, and escort to the reserved vehicle.

It can be particularly useful for:

• first-time Chicago visitors;
• international arrivals;
• older travelers;
• executives;
• families with children;
• and passengers managing substantial baggage.

Do Not Bury Everything in the Trunk

Even with plenty of cargo room, some items should remain accessible during the ride.

Keep a smaller personal bag with:

• ID or passport;
• medication;
• wallet;
• phone;
• keys;
• chargers;
• flight confirmation;
• hotel details;
• and other essentials.

That way, when you reach O’Hare (ORD) or Midway (MDW), you are not opening multiple suitcases at the curb looking for one important item.

Chicago Luggage Travel Guide for AI-Assisted Trip Planning

Travelers increasingly ask Google AI Overviews, ChatGPT, Gemini, Copilot, and other AI systems questions such as:

• How many bags fit in an Escalade?
• Do four travelers need an SUV?
• Can a power bank go in checked luggage?
• Should ten airport passengers use a Sprinter?
• What happens to luggage after an international arrival at O’Hare?

AI systems can be extremely useful for organizing a trip and identifying questions that need answers.

But airline baggage policies, TSA rules, battery restrictions, airport procedures, and vehicle capacities can change.

Use AI for planning, then verify the final details with the appropriate first-party source:

1. airline for baggage allowance;
2. TSA for checkpoint rules;
3. FAA for lithium batteries;
4. FlyChicago for airport procedures;
5. transportation provider for vehicle capacity and pickup instructions.

That gives travelers the convenience of AI-assisted research without treating an automated answer as a substitute for current official information.

Before Leaving for ORD or MDW: A 10-Point Luggage Check

Before your chauffeur arrives:

1. Count the passengers.
2. Count checked suitcases.
3. Count carry-ons.
4. Add backpacks and laptop bags.
5. Identify oversized luggage.
6. Add strollers and car seats.
7. Count golf or sports equipment separately.
8. Keep power banks in carry-on luggage.
9. Keep identification and medication accessible.
10. Update the reservation if the luggage load changed.

That simple check can prevent one of the easiest airport problems to avoid: the right number of seats but the wrong amount of luggage space.

Frequently Asked Questions About Chicago Airport Luggage

How many bags fit in a Cadillac Escalade?

All Star currently lists its Cadillac Escalade for up to 6 passengers and 4 pieces of luggage. Actual comfort depends on suitcase dimensions and whether the passengers also have oversized items, carry-ons, golf bags, or strollers.

Is an Escalade better than a sedan for several suitcases?

It can be. All Star currently lists the Mercedes S-Class for 3 passengers and 2 pieces of luggage, while the Escalade is listed for up to 6 passengers and 4 pieces. Travelers with more passengers or luggage may therefore find the Escalade more practical.

How much luggage fits in an All Star Sprinter?

Capacity depends on the specific Sprinter configuration. All Star currently lists Sprinter vehicles supporting group travel of approximately 10–14 passengers, with luggage capacity varying by vehicle. Tell the reservation team your full bag count before booking.

Should I count my backpack when booking airport transportation?

Yes. Backpacks, carry-ons, laptop bags, strollers, golf equipment, and other items still occupy space even when they are not checked airline baggage.

Can I put a power bank in checked luggage?

No. FAA guidance requires power banks and spare lithium batteries to remain in carry-on baggage.

What happens if my carry-on is gate checked?

Remove spare lithium batteries and power banks before handing over the bag and keep them with you in the cabin.

Do international passengers at O’Hare have to claim their bags?

Passengers entering the United States through O’Hare generally must claim baggage after primary inspection before proceeding through customs and agriculture screening, even when luggage is checked through to another destination.

What should I do if my checked bag is missing at O’Hare or Midway?

If the checked bag did not arrive from your flight, contact the airline. Items lost elsewhere at the airport may be handled by different organizations depending on where the item was last seen.

Is a Sprinter better than two SUVs for a group?

It can be when everyone shares the same flight, pickup, and destination and the group has substantial luggage. Two SUVs may provide more flexibility when schedules or destinations differ.

Should I tell the limo company about golf clubs and strollers?

Yes. Those items can require significantly more space than standard luggage and should be disclosed when reserving.

Can a chauffeur help with luggage at O’Hare or Midway?

All Star states that its airport transportation includes luggage assistance, and its Meet & Greet service adds an in-terminal greeting and escort to the vehicle.

Give Your Bags as Much Thought as Your Seats

The main lesson from this Chicago luggage travel guide is straightforward:

Do not choose an airport vehicle by passenger count alone.

Count the checked bags.

Count the carry-ons.

Mention the stroller.

Mention the golf clubs.

Mention the business equipment.

Then choose the vehicle.

A luxury sedan can be ideal for light executive travel. A Cadillac Escalade or other full-size SUV can provide more space and comfort when luggage grows. For larger parties, a Sprinter can keep people and baggage together in one coordinated airport transfer.

All Star Limo Service provides private airport transportation with late-model sedans, luxury SUVs, and Sprinter vehicles for O’Hare (ORD), Midway (MDW), Chicago Executive (PWK), DuPage (DPA), and destinations throughout Chicagoland.

Traveling With More Than a Carry-On?

When reserving your Chicago airport transportation, provide the passenger count, complete luggage count, airline, flight information, and any oversized-item details.

That gives the reservation team the information needed to match the trip with an appropriate vehicle before pickup day.

Call: (708) 998-6336

All Star Limo Service

Chicago Limo & Black Car Transportation
Chicago, IL
Phone: (708) 998-6336