Chicago Midway International Airport (MDW) Trip Planner Are you planning a trip to Chicago Midway International Airport (MDW)? Start planning your itinerary on GAFFL. Here’s how:

Pick A Trip Type

Click on “Start A Trip” and pick your Trip Type

Choose Your Destination

Choose Chicago Midway International Airport (MDW) as your destination and select how long your trip in Chicago Midway International Airport (MDW) will be

Input Your Trip Details

Create a title for your trip and describe it by including things you will do and places you will visit in Chicago Midway International Airport (MDW)

Start Your Trip

Select a meet up point and if other users on GAFFL like your trip itinerary, they can request to connect and meet up with you in Chicago Midway International Airport (MDW)
WAQAS
Celebrating New Year in Chicago
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Chicago
Dec 27, 2025 - Jan 3, 2026
Join me in celebrating New Year in Chicago! Explore the city's vibrant energy, stunning architect...
Noël
Chicago Solo Trip
Explore Chicago with Noël
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Apr 6, 2026 - Apr 12, 2026
I Hey! I’m planning to go to Chicago from April 6th to 12th. My idea is to keep it chill—check ou...
Sena
Chicago short trip
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Join Sena for this road trip to Chicago
Chicago
Dec 18, 2025 - Dec 21, 2025
International student from Tokyo, Japan.Short trip to Chicago during Christmas break.I wanna visi...
varun
a week in Chicago
Explore Chicago with varun
Chicago
Dec 14, 2025 - Dec 20, 2025
Traveling to Chicago for a week and would love to catch up with someone traveling solo like me.
Gijo
New Year Trip
Join Gijo on his Adventure Travel to Chicago
Chicago
Dec 28, 2025 - Jan 4, 2026 (Flexible)
Destination is not fixed yet. 

Chico
Chico
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Connect with Chico to know about the hidden gems of Bridgeport, Chicago, IL, USA
Connect with Chico to explore Bridgeport, Chicago, IL, USA together
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Bridgeport, Chicago, I...
Let’s Understand the culture and what the best activities the country has to offer
Mark
Mark
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Connect with Mark to know about the hidden gems of Chicago
Connect with Mark to explore Chicago together
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Connect and use Mark's travel and outdoor equipment
Chicago
I live in Palatine. About 30-45min NW of Chicago, depends on traffic. I have only lived in the ...
Adam
Adam
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Connect and stay in Adam's home
Connect with Adam to know about the hidden gems of Chicago
Connect with Adam to explore Chicago together
Chicago
City of Chicago local looking to introduce folks to this amazing city.
sameer
sameer
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Connect and lend sameer's vehicle or get a ride
Chicago
Weekend party , airport pick up
Dane
Dane
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Chicago
Aloha! I grew up in Hawaii and love Chicago. Public transit is great and Chicago is the land of...
Christina
Christina
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Chicago
I am always down for ood/coffee/drinks and hanging out
Darnell
Darnell
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Chicago, IL, USA
I’m into photographing art and murals. Also I like trying new restaurants!
Peter
Peter
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Connect with Peter to know about the hidden gems of Chicago, IL, USA
Chicago, IL, USA
The touristy things in Chicago are fine but to experience the city for real, you gotta get away f...

Shawn
Shawn
Grant Park
Male, Age 49
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Divorced and looking to travel. Love both leisure and adventure.
Bill
Bill
Cleveland
Male, Age 43
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I’ve travelled a lot for work. Now I have more free time and I’m interested in active travel and ...
Jaclyne
Jaclyne
Toronto
Female, Age 32
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Looking for like-minded people who want to travel, adventure, and try new things with me.
RG
RG
Windsor
RG
Male, Age 39
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I’m a single educator from India, living and working in Toronto. I’m traveling to UK July 1-8 and...
Aarti
Aarti
Waukegan
Female, Age 40
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Hey there! I am a borderline workaholic and I run off on a vacation whenever I can. I work to tra...
Ross
Ross
St. Louis
Male, Age 41
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Hello! My name is Ross and I'm a remote-work programmer by day and a martial arts instructor by n...
ferdi
ferdi
Mason City
Male, Age 42
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I’m someone who loves discovering new places, is open to learning, and turns every trip into an a...
Breanna
Breanna
Brampton
Female, Age 21
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I love traveling and am hoping to find travel friends preferably female. Just want to explore and...

FAQ

Why is GAFFL the best website/app for planning a trip to Chicago Midway International Airport (MDW) ?

It is completely free to start planning your trip to Chicago Midway International Airport (MDW) on GAFFL. You can keep all of your trip details in one place, including things you’ll do, places you’ll visit, where you’ll stay, and when you’ll fly. Also, after you’ve planned your trip, GAFFL helps you connect with other like-minded travelers planning a similar trip at the same time as you.

How do I plan a trip to explore different cities on GAFFL?

Planning a trip to explore cities on GAFFL is entirely free and very easy. Click on ‘Start A Trip’ and select ‘Explore Cities’ as your trip type. Then after providing your current location, select the city you want to plan your trip to. Create a title for your city exploration trip and describe things you’ll want to do and places you will want to visit. Then select a public place as a meetup point before or during your trip. You can also book hotels in that city and flights to that city and keep the information stored within your trip itinerary. Someone planning a similar trip can request to connect, meet up, share costs, and explore the city with you.

How can I plan a road trip to Chicago Midway International Airport (MDW) on GAFFL?

Planning a road trip to Chicago Midway International Airport (MDW) is completely free on GAFFL. Click on ‘Start A Trip’ and select ‘Road Trip’ as your trip type. Then choose where you’re planning to start your road trip and where you want to finish it. Create a title for your road trip and describe things you’ll do and places you want to visit while on the road. Then select a public place as a meetup point before or during your trip. Someone planning a similar road trip can request to connect with and together you can split costs for things like rental cars and lodging.

How do I plan a backpacking or hiking trip on GAFFL?

Planning a backpacking/hiking trip is absolutely free on GAFFL. Click on ‘Start A Trip’ and select ‘Adventure Travel’ as your trip type. Then choose your specific destination or a hiking trail and select the duration of your trip. Name your upcoming backpacking/hiking trip with a title and let others know the details of the trip in the description. Then select a meetup point in a public place. If other adventurers like your trip, they can request to connect and meetup with you.
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