Chicago Trip Planner Are you planning a trip to Chicago? 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 as your destination and select how long your trip in Chicago 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

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
B
Chicago Trip
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Explore Chicago with B
Chicago
Apr 19, 2025 - Apr 23, 2025
Going with a group of friends but would like to find a companion to join me and show me around. ...
Nicole
chicago trip
Join Nicole on his Adventure Travel to Chicago
Chicago
May 20, 2025 - May 26, 2025
Hi! I am looking for somebody (woman please I am in a relationship currebtly) to travel with me t...
allison
Gettin' Our Kicks on Route 66
Join allison for this road trip to Chicago
Chicago
Jun 8, 2025 - Jun 29, 2025 (Flexible)
*Update : I have one more spot confirmed and two who are interested. Any others interested will b...
Joshua
Adventure in Italy 🇮🇹
Join Joshua on his Adventure Travel to Grand Italian Trail
Grand Italian Trail
Jul 31, 2025 - Aug 10, 2025 (Flexible)
I’m looking for someone fun to go on an adventure in Italy with. I’m a 39-year-old gay man and al...

MTI
MTI
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Connect with MTI to meet up for coffee or drink
Connect with MTI to know about the hidden gems of Chicago
Connect with MTI to explore Chicago together
Chicago
Welcome to Chicago, my current hometown! When you visit, let's ditch the touristy spots and dive ...
Mark
Mark
Connect with Mark to meet up for coffee or drink
Connect with Mark to know about the hidden gems of Chicago
Connect with Mark to explore Chicago together
Connect and lend Mark's vehicle or get a ride
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
Connect with Adam to meet up for coffee or drink
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
Connect with sameer to meet up for coffee or drink
Connect and lend sameer's vehicle or get a ride
Chicago
Weekend party , airport pick up
Dane
Dane
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Connect with Dane to know about the hidden gems of Chicago
Chicago
Aloha! I grew up in Hawaii and love Chicago. Public transit is great and Chicago is the land of...
Christina
Christina
Connect with Christina to meet up for coffee or drink
Chicago
I am always down for ood/coffee/drinks and hanging out
Darnell
Darnell
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Connect with Darnell to meet up for coffee or drink
Chicago, IL, USA
I’m into photographing art and murals. Also I like trying new restaurants!
Peter
Peter
Connect with Peter to meet up for coffee or drink
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...

Bill
Bill
Cleveland
Male, Age 42
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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 ...
Aarti
Aarti
Waukegan
Female, Age 39
Verified by
Hey there! I am a borderline workaholic and I run off on a vacation whenever I can. I work to tra...
Jaclyne
Jaclyne
Toronto
Female, Age 32
Verified by
Looking for like-minded people who want to travel, adventure, and try new things with me.
Michaela
Michaela
Grand Rapids, Michigan
Female, Age 23
Verified by
Looking for some trustworthy girls to adventure with! I'm pretty laid back and easy to get along ...
Elijah
Elijah
Madison, Wisconsin
Male, Age 20
Verified by
Looking for people to travel with, I’ve been wanting to hit up New York just haven’t found anyone...
Prairie
Prairie
Cedar Rapids
Female, Age 37
Verified by
I'm always up for an adventure or just chilling on the beach with a cocktail
Anjana
Anjana
Toronto
Female, Age 35
Verified by
Thinking
Ross
Ross
St. Louis
Male, Age 40
Verified by
Hello! My name is Ross and I'm a remote-work programmer by day and a martial arts instructor by n...

FAQ

Why is GAFFL the best website/app for planning a trip to Chicago ?

It is completely free to start planning your trip to Chicago 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 on GAFFL?

Planning a road trip to Chicago 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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