Chicago Getaway

Personalized Chicago Trip Gifts & Essentials

Shop personalized Chicago vacation gifts, travel accessories, drinkware, tote bags, and welcome bag essentials for city adventures, family vacations, girls weekends, and group getaways. Celebrate the Windy City with personalized travel favorites designed for memorable trips and iconic skyline views.

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  • Most Likely To Funny Baseball Hats Most Likely To Funny Baseball Hats
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    Most Likely To Funny Baseball Hats

    Get the group laughing with our Most Likely To hats for women. Featuring fun sayings that highlight each friend's personality, these hats are perfect for girls trips, bachelorette parties, birthday weekends, vacations, lake trips, beach getaways, and...
    $9.99
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  • A Tini Bit Hungover Sleep Masks A Tini Bit Hungover Sleep Masks
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    A Tini Bit Hungover Sleep Masks

    Recover in style with “A Tini Bit Hungover” martini sleep masks, designed for bachelorette parties, girls trips, and weekend celebrations. These playful eye masks combine humor with comfort, making them the perfect favor for your group. Soft,...
    $7.99
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  • Tini Bit Tipsy Can Coolers Tini Bit Tipsy Can Coolers
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    Tini Bit Tipsy Can Coolers

    Turn up the cocktail energy with our Personalized “A Tini Bit Tipsy” Can Coolers. Designed for bachelorette parties, girls weekends, and birthday trips, these custom drink sleeves feature your choice of classic martini or espresso martini...
    $4.00
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  • Oh Sip Martini 16oz Clear Cups Oh Sip Martini 16oz Clear Cups
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    Oh Sip Martini 16oz Clear Cups

    Whether you're sipping espresso martinis with your bride squad or toasting another year around the sun, these custom "Oh Sip Martini" 16oz party cups are made to serve major party vibes. Choose a bow for extra flair — or skip it if you like your...
    $4.99
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  • Bikinis and Martinis 16oz Clear Cups Bikinis and Martinis 16oz Clear Cups
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    Bikinis and Martinis 16oz Clear Cups

    Shake up your next girls trip or poolside party with our Bikinis & Martinis 16oz Custom Party Cups – the ultimate personalized drinkware for bachelorette weekends, tropical birthdays, or espresso martini-fueled girls getaways! Choose between...
    $4.99
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  • Martini Fan Martini Fan
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    Martini Fan

    Shake up your celebration with our Martini Custom Bachelorette Party Fans – the chic and cheeky favor that keeps your crew cool while turning up the style! Whether you're celebrating a beachside bachelorette, destination wedding, or a “Tini...
    $2.99
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  • Just in Case Heart Recovery Kit Bags Just in Case Heart Recovery Kit Bags
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    Just in Case Heart Recovery Kit Bags

    Add a thoughtful and practical touch to your celebration with our Joy & Chaos Just In Case recovery kit bags featuring a classic cross design, available with or without a heart. Perfect for wedding welcome bags, bulk guest favors, bachelorette...
    $2.45
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  • Just in Case Champagne Recovery Bags Just in Case Champagne Recovery Bags
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    Just in Case Champagne Recovery Bags

    Add a refined and practical touch to your celebration with our Joy & Chaos Just In Case wedding recovery kit bags. Featuring a clean, modern design with customizable text, these cotton favor bags are ideal for wedding welcome gifts, bridal showers,...
    $2.45
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  • Martini Luggage Tags Martini Luggage Tags
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    Martini Luggage Tags

    Add a chic, playful touch to your next getaway with personalized martini luggage tags. Perfect for bachelorette parties, girls trips, and destination weekends, these tags bring personality and style to every bag. Choose between a classic martini or...
    $7.99
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  • Cosmopolitan Baseball Hats Cosmopolitan Baseball Hats
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    Cosmopolitan Baseball Hats

    These custom cosmo cocktail baseball hats are perfect for a New York bachelorette, girls trip, social club birthday, or other boozy celebration.  PERSONALIZATION Add a name or location (printed in script - up to 12 characters maximum) Optional side...
    $9.99
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  • Chicago Welcome Bags Chicago Welcome Bags
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    Chicago Welcome Bags

    These personalized "Welcome to Chicago" city skyline bags are perfect for a trip to Chi-Town, a Windy City wedding, vacation, bachelorette, or other special event in Chicago. Choose from several sizes of our popular drawstring canvas bags and customize...
    $2.45
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  • Chicago Welcome Tote Bags Chicago Welcome Tote Bags
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    Chicago Welcome Tote Bags

    These personalized "Welcome to Chicago" city skyline tote bags are perfect for a trip to the Windy city, a hometown wedding, or other special event. Choose from our canvas drawstring backpacks or our gusseted premium totes or eco canvas tote bags...
    $8.50
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  • City Welcome Bags City Welcome Bags
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    City Welcome Bags

    These personalized "Welcome to..." city skyline bags are perfect for a trip, wedding, vacation, bachelorette, or other special event. Choose from several sizes of our popular drawstring canvas bags and customize with the design color and 1-2 lines of...
    $2.45
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  • Cosmpolitan Oh Sip Recovery Kit Bags Cosmpolitan Oh Sip Recovery Kit Bags
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    Cosmpolitan Oh Sip Recovery Kit Bags

    Keep the celebration cute from cocktails to recovery with our Joy & Chaos Oh Sip Cosmopolitan favor bags. Featuring a stylish cosmo glass design and up to two lines of custom text, these cotton favor bags are perfect for girls’ trips, adult...
    $2.45
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  • Martini Oh Sip Recovery Kit Bags Martini Oh Sip Recovery Kit Bags
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    Martini Oh Sip Recovery Kit Bags

    Toast in style and recover cutely with our Joy & Chaos Oh Sip martini favor bags. Featuring a classic martini glass design available with or without a pink bow and up to two lines of custom text, these cotton favor bags are perfect for birthdays,...
    $2.45
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  • Hangover Recovery Kit Bags Hangover Recovery Kit Bags
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    Hangover Recovery Kit Bags

    These hangover kit bags are the perfect favor for a boozy bash. Each reusable 4" x 6" drawstring canvas bags comes with your choice of our pink or red "Hang Over Recovery Kit" design, and are just the right size for your favorite day after remedies or...
    $1.95
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  • Sunshine Tote Bags Sunshine Tote Bags
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    Sunshine Tote Bags

    Customize these canvas tote bags for a Mexico vacation, trip to Cancun, or any south of the border celebration. Our modern sunshine design is available on several sizes of drawstring canvas gift bags, our canvas drawstring backpacks, or our popular...
    $2.45
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  • Custom Chicago Tote Bags - Personalized Chicago Bags with Handles, Canvas Totes for Chicago Wedding Custom Chicago Tote Bags - Personalized Chicago Bags with Handles, Canvas Totes for Chicago Wedding
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    Chicago Star Tote Bags

    These customized Chicago star tote bags are a classic choice for a Windy City wedding, vacation, or Chi-Town special occasion. Choose our best-selling heavy canvas tote bags, lightweight economy totes, or drawstring canvas backpacks and personalize with...
    $8.50
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  • Windy City Chicago Bags Windy City Chicago Bags
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    Windy City Chicago Bags

    Our customized "The Windy City - Chicago" bags are perfect for a Chi-Town getaway or special event. Choose from three sizes of drawstring gift or favor bags, and personalize with 1-2 lines of your own custom text. Personalization Add 1-2 lines of...
    $2.95
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  • Custom Chicago Tote Bags - Personalized Canvas Totes for Chicago Trip or Event Custom Chicago Backpacks - Personalized Canvas Drawstring Backpacks for Chicago Trip or Event
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    Windy City Chicago Tote Bags

    These bold customized Chicago tote bags are perfect for a Windy City getaway. Choose our best-selling heavy canvas tote bags, lightweight economy totes, or drawstring canvas backpacks and personalize with 1-2 lines of text. Personalization Add 1-2 lines...
    $8.50
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  • Chicago Flag Tattoos - Custom Chicago Bachelorette Tattoos - Chicago Birthday Party Temporary Tattoos - Personalized Chicago Party Favors Chicago Flag Tattoos - Custom Chicago Bachelorette Tattoos - Chicago Birthday Party Temporary Tattoos - Personalized Chicago Party Favors
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    Chicago Flag Heart Tattoos

    Show your love for the Windy City with these customized Chicago flag heart tattoos. This set of temporary tattoos is personalized with a name and the event you are celebrating in Chi-town!  Set of 12 tattoos.Application instructions are included...
    $12.99
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  • Gettin Down in Chi-Town Can Coolers Gettin Down in Chi-Town Can Coolers
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    Gettin Down in Chi-Town Can Coolers

    Celebrate your Chicago event in style with our Custom Chicago Skyline Can Coolers. Featuring a bold skyline design and “Gettin Down in Chi Town” energy, these drink sleeves are perfect for birthdays, weddings, bachelorette parties, and...
    $4.00
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  • Windy City Hair Tank or Shirt Windy City Hair Tank or Shirt
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    Windy City Hair Tank or Shirt

    Our Windy City Hair design is available on your choice of classic women's racerback tank top or soft premium cotton jersey unisex tee. Rep Chicago and our wild weather with this fun shirt! Tank Tops 40% polyester, 60% ringspun cotton Combed ringspun...
    $12.99
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  • Chicago Skyline Welcome Gift Bag + Box Stickers Custom Chicago Party Favor Labels - Round Personalized Stickers
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    Chicago Skyline Favor Labels

    Welcome guests to a Windy City wedding, conference in chicago, or any special event in Chi-town with these modern personalized favor labels. Choose the design color and custom select sticker styles with 1-2 lines of text and the event date.These skyline...
    $6.00
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  • Custom Logo Beach Tote Bags Custom Logo Beach Tote Bags
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    Custom Logo Beach Tote Bags

    Create premium custom canvas tote bags personalized with your logo, artwork, or photo. Whether you're promoting your business, hosting an event, or creating memorable welcome gifts, these reusable canvas totes combine professional branding with everyday...
    $24.00
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  • Modern City Skyline Can Coolers Modern City Skyline Can Coolers
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    Modern City Skyline Can Coolers

    Customize a set of these modern city skyline can coolers for a destination wedding, birthday vacation, girls trip, or a hometown celebration! Choose the skyline print color and add your custom text to create a unique party favor.   AVAILABLE...
    $4.00
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  • Classic Cross Survival Kit Favor Bags Classic Cross Survival Kit Favor Bags
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    Classic Cross Survival Kit Favor Bags

    Create the ultimate party favor with our Joy & Chaos custom survival kit bags. Featuring personalized text and your choice of icon, these cotton favor bags are perfect for bachelorette parties, birthday trips, and girls’ getaways where a little...
    $2.45
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  • Custom Chicago Skyline Tote Bags for Chicago Girls Trip, Chicago Birthday Vacation, Chicago Reunion - Personalized Chicago Vacation Bags Custom Chicago Skyline Tote Bags for Chicago Girls Trip, Chicago Birthday Vacation, Chicago Reunion - Personalized Chicago Vacation Bags
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    Gettin' Down in Chicago Tote Bags

    These modern Gettin' Down in Chi-Town personalized Chicago skyline totes are perfect for a Windy City birthday, girls trip, reunion or vacay.This design is available on our best-selling canvas tote bags or drawstring canvas backpacks...
    $8.50
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  • Gettin' Down in Chicago Bags Gettin' Down in Chicago Bags
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    Gettin' Down in Chicago Bags

    These Gettin' Down In Chi-Town custom party favor bags come with our modern Chicago skyline design, and are perfect for a Windy City birthday, girls trip or reunion.This design is available on three sizes of drawstring gift or favor bags. Personalization...
    $2.95
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  • Personalized Chicago Love & Pride Tote Bag Chicago Love & Pride Tote Bag
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    Chicago Love & Pride Tote Bag

    Personalize your tote by adding a neighborhood, location or other custom text, using up to 20 characters.Your item has been made especially for you and is a final sale. Premium Tote Bag Details 100% heavy natural cotton canvas (12.0 oz) Size: approx...
    $9.50
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  • Custom Logo: Natural Canvas Tote Bag Custom Logo Tote Bags: Natural Canvas Tote Bag with Full Color Print for Your Artwork or Design
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    Custom Logo: Natural Canvas Tote Bag

    Have your custom logo or original artwork printed in full color on our best-selling heavy natural canvas tote bags! Available with either black or natural colored handles, these durable, useful totes are perfect for small businesses, special events such...
    $6.50
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  • Custom Logo: Canvas Drawstring Backpack (Full Color Print) Custom Logo: Canvas Drawstring Backpack
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    Custom Logo: Canvas Drawstring Backpack

    Have your custom logo or artwork printed in full color on our natural canvas drawstring backpacks. These customized bags are perfect for group trips, bar & bat mitzvahs, birthdays, sports teams, small businesses, and special events. Why choose us?We...
    $19.50
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