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Vacation Babysitters Chicago, IL (Contact for Free)

Hire a vacation babysitter to travel with you on holiday, so you can enjoy both family time and some grown-up relaxation. See our Pay Rates.

Show all babysitters in Chicago


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Isyss Lee
Chicago, IL

Activity summary

Member since: Mar 2023

Vacation Babysitter, Babysitter

Child ages I'm comfortable caring for:

  • Toddlers (1 - 2 years)
  • Preschoolers (3 - 4 years)
  • Small school kids (5 - 8 years)
  • Tweens (9 - 12 years)
  • Teenagers (13+ years)
  • Up to 4 children at once

My availability

I'm looking for Casual/temporary, Full-time employment.

I can travel to neighboring suburbs/towns of Chicago for work.

Here's my weekly availability:

M T W T F S S

Morn

✓ ✓ ✓ ✓ ✓ ✓ ✓

Day

✓ ✓ ✓ ✓ ✓ ✓ ✓

Arvo

✓ ✓ ✓ ✓ ✓ - ✓

Eve.

✓ ✓ ✓ ✓ ✓ - -

Nite

- - - - - - -

I'm available for:

  • Last minute bookings
  • School holidays
  • Overnight jobs
  • Full weekends
  • Vacations with the family

My credentials

I'm happy to provide written documentation of my qualifications and credentials:

  • General credentials:
    • Email verified
    • 21 years old
    • Languages I can speak: English

Contact Isyss For Free

Your job requirements will be sent with your message.

Select the services you need:

Childcare

How many kids need care?

Pet sitting

Other pet services you need:

Dog walking

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Babysitting Pay Rates Chicago, IL, United States (Updated 5 Oct 2025)

Chicago babysitters are paid an average of $20.14 per hour as of October 2025, which is 0.7% higher than the Illinois average of $20.01, and 9.3% higher than the United States average of $18.43. A fair pay rate depends on babysitter credentials, specific job requirements, and local demand for babysitting services in Chicago.
1 Kid 2 Kids 3+ Kids
Chicago:
$18.31 $20.14 $21.97
Illinois:
$18.19 $20.01 $21.83
United States:
$16.75 $18.43 $20.10

Rates are calculated weekly from our live member data. Prices are shown in United States dollars (USD). If you republish our rates please credit kidsit.com 😊

Don't know how much to pay? See our parents' guide to babysitting pay rates


Top 10 Tips For Hiring A Vacation Babysitter

Follow these handy tips when hiring a vacation babysitter so everyone can get the most out of your family holiday.

1. Start your search early

Traveling babysitters are in high demand, so begin looking several months before your trip.

2. Choose someone with travel experience

Ask if they’ve traveled with families before and are comfortable with airports, hotels, and long days.

3. Check passports and paperwork

Ensure the babysitter has a valid passport, visas (if needed), and is comfortable with any travel requirements.

4. Discuss schedules and expectations

Be clear about when you’ll need childcare versus family time, so boundaries are understood.

5. Cover all expenses upfront

Agree on who pays for flights, accommodations, meals, and any extras before the trip.

6. Set pay rates clearly

Holiday babysitting often involves long hours; discuss a fair daily or weekly rate plus overtime if needed.

7. Review responsibilities

Clarify whether the sitter will supervise only in the hotel/villa or accompany your children on excursions.

8. Do a trial run at home

Have the sitter spend time with your kids before the trip to build trust and routine familiarity.

9. Check adaptability

Make sure they’re flexible with changes, new environments, and possible travel hiccups.

10. Trust and comfort are key

Since you’ll be spending extended time together, choose someone you not only trust with your children but also feel comfortable traveling with.

See our parents' guide to vacation babysitting for more detailed information.

Vacation Babysitter Interview Questions

Ask the following questions when interviewing vacation babysitter candidates to narrow down your list.

Travel Readiness

  • Have you ever traveled with a family before? What was your role?
  • Do you have a valid passport (and visas if required)?
  • Are you comfortable with airports, flights, and adjusting to new environments?
  • How do you handle long travel days or jet lag?

Childcare Experience

  • What ages of children have you cared for while traveling?
  • How do you keep kids entertained in hotels, airplanes, or on long car rides?
  • Are you comfortable supervising children at pools, beaches, or tourist attractions?
  • How would you handle a child becoming homesick or overwhelmed on vacation?

Responsibilities & Flexibility

  • Are you open to both daytime and evening shifts while traveling?
  • How do you balance giving parents alone time with including you in family activities?
  • What types of activities or outings are you comfortable managing on your own with the kids?
  • How flexible are you if plans change last minute?

Safety & Health

  • Are you certified in CPR and first aid?
  • How would you handle a medical emergency in a foreign country?
  • Are you comfortable administering medication if needed?
  • How do you ensure children’s safety in unfamiliar environments?

Pay & Expenses

  • What is your preferred rate for travel babysitting (daily/weekly)?
  • Are you comfortable with travel arrangements (flights, accommodations, meals) being covered by the family?
  • Do you expect overtime pay for late-night care?
  • How do you prefer payments to be handled during the trip?

Personality & Fit

  • What do you enjoy most about traveling with children?
  • How do you keep calm and positive when travel gets stressful?
  • Why are you interested in traveling as a babysitter?
  • What makes you a good fit for our family and this trip?