Custom Itinerary Request Form


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We know planning a trip can be exhausting.The hotels, the tours, even picking a restaurant seems like a daunting task. So let us help you. We’ll make sure you hit all the best spots and get in as much as possible, no matter how long your visit is! Just fill out the form below and we’ll get back to you!

Pricing & Payment:
$10 per day / plus $3 processing fee

Payment is accepted with credit card or via PayPal account transfer.

Itineraries do not include the price of any tours or tickets. All tours and tickets must be purchased separately, though we would be happy to schedule them for you at no extra charge! Just let us know.

**We are also in the process of developing basic, non-customized itineraries for $5 a day. Please let us know if you are interested in that option by emailing us here.



Your Full Name (required)

Your Email (required)



Travel Dates

// - //

 Unsure Flexible

How many days would you like us to plan for you?


Just out of curiosity, where will you be visiting from?



What's the average age in your group?
 0-12 13-20 21-35 46-60 60+

Will you be traveling with children?
 Yes No

Tell us what you're interested in doing!

 ArchitectureTour
 Art Galleries/Museums
 Beach
 Bike Tour
 City Tour
 Concert/Live Music
 Double-Decker Bus Tour
 Eco-Friendly Activities
 Food Tours
 Gangster Tour
 Gay-Friendly Activities
 Holiday Celebrations (Seasonal)
 John Hancock Center Observatory
 Kid-Friendly Activities
 Lake Cruises
 Millennium Park/The Bean
 Museums
 Navy Pier
 Segway Tour
 Sears (Willis) Tower Observatory
 Shopping
 Guided Shopping Tour
 Sports Game
 Street Fairs/Festivals
 Theatre
 Zoo
 Other(s) (Let us know below!)



Would you like us to pick out restaurants for you?

If so, what kind of places do you like?

 Everything (I'm adventurous!)
 Al Fresco
 American
 Chinese
 Chicago-Style Deep Dish Pizza
 French
 Fusion
 Local Tastes
 GastroPub
 Greek
 Indian
 Italian
 Japanese/Sushi
 Kid-Friendly
 Korean
 Mexican
 Pizza
 Thai
 Steakhouses
 Vegan
 Vegetarian
 Other (Let us know below!)



Anything else we should know about your trip and interests?


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About UPchicago Team

Urban Philosophy is a way of thinking that you develop when you’re a true city person. Whether you’ve spent your whole life living in Manhattan, or you just moved from small-town Iowa to the city of Chicago, the longer you stay, the more you come to understand what it means to live in a city. Our Urban Philosophy is that no matter who you are, where you are from, and what your likes and dislikes may be, there’s something for everyone in city life.

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