Jen • Chicago Travel & Lifestyle Instagram Profile Picture

Jen • Chicago Travel & Lifestyle

@ontheroadwithjen

Travel & Lifestyle Creator, Content Creator, Blogger
Chicago lifestyle with a side of travel ✈️ 💌 ontheroadwithjen@gmail.com
Travel Lifestyle
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Top Instagram Posts of Jen Chicago Travel Lifestyle

Jen Chicago Travel Lifestyle’s Most liked posts from the last 30 uploads.

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Media Stats – Instagram Posts

Recent 30 posts with likes and comments overview.

Media overview
Published Caption Likes Comments
“Describe your perfect day” sevenstarsresort #TurksAndCaicos #SevenStarsHotel #CaribbeanTrip #CaribbeanVacation #CaribbeanTravel #SummerBucketlist #IslandTravel #CaribbeanLife 2025-09-21 21:41:09 “Describe your perfec.. 0 - 10 -59%
Had the most wonderful brunch experience at thealbertchicago nestled in the coziest corner of Streeterville. Brunchissimo is their Italian coastal experience, served family style from 11a—2p on Saturday and Sunday 🥂 In addition to the great food, the ambiance was perfect with live music and an outdoor seating option. So perfect for the early fall season. thealbertchicago #chicagofoodie #chicagorestaurants #chicagodining #chicagoeats #downtownchicago #chicagofood #chicagobrunch #chicagohappyhour #chifoodie #wheretoeatinchicago 2025-09-20 20:31:05 Had the most wonderf.. 0 - 21 -14%
On this day two years ago 🌳 By far one of the most unique places I’ve ever been to - The Hoh Rainforest in Olympic National Park. It felt like I was walking inside a storybook and so worth the drive when visiting Seattle or the surrounding park area 🌿 2025-09-16 23:17:53 On this day two y.. 0 - 29 +18%
Unfortunately, I am also hopping on this trend before it’s over 🙃 #unfortunatelyidolove 2025-09-15 23:25:06 Unfortunately, I am .. 0 - 18 -26%
The perfect beachy afternoon 🥂 2025-09-15 00:54:35 The perfect beachy aft.. 0 - 20 -18%
Chicago, it’s not too late for some rooftop fun at iogodfrey for their “Bubbles & Boards” Happy Hour everyday from 5-7p which includes chef’s selection of cheese + charcuterie and a bottle of prosecco 🥂 We also tried a few other menu items like their flatbread pizza, wagyu sliders and Godfrey roll - all of which were great. 📍 iogodfrey in River North #chicagofoodie #chicagorestaurants #chicagodining #chicagoeats #downtownchicago #chicagofood #chicagorooftop #chicagohappyhour #rivernorthchicago #chifoodie 2025-09-11 23:22:58 Chicago, it.. 0 - 19 -22%
What makes me happy? A poolside cabana and chicken caesar wrap 💦 📍 sevenstarsresort has private cabanas you can reserve for the day (at the adults-only pool) that come with two complimentary beverages and an incredible waitstaff to make your day perfectly relaxing #turksandcaicos #SevenStarsHotel #CaribbeanTrip #CaribbeanVacation #CaribbeanTravel #SummerBucketlist #IslandTravel 2025-09-08 23:02:01 What makes me happy.. 0 - 23 -6%
White after Labor Day cause I was never one for following the rules 🤍 2025-09-06 21:18:16 White after Labor Day .. 0 - 25 +2%
That 2 hour break between a beach day and dressing up for dinner >>> These balcony views at sevenstarsresort were just amazing #sevenstars #TurksAndCaicos #SevenStarsHotel #CaribbeanTrip #CaribbeanVacation #CaribbeanTravel #SummerBucketlist #caribbeanlife 2025-09-05 23:07:29 That 2 hour break between.. 0 - 19 -22%
Weekend mornings moving my body >>> I’ve biked and walked past Museum Campus more times than I can count but never actually walked into this specific garden area. So nice on a sunny day! Really making an effort to prioritize my mental health as we move into a slower season in the city. Saying “yes” to every plan this summer was fun, but trying to be intentional on making time for me 🫶🏻 Wearing fabletics #fableticspartner #chicago #chicagotravel #visitchicago #lakemichigan #thingstodoinchicago #chicagolifestyle #chicagolife 2025-09-04 23:20:24 Weekend morni.. 0 - 14 -43%
Tried a few of the new menu offerings at Dearly Beloved last week and they were just 🤌🏻 I’m also equally obsessed with the interior design of this restaurant! 2025-09-03 23:45:15 Tried a few of th.. 0 - 32 +31%
Spend a travel day with me with a very early alarm and subsequently a very early bedtime 🙂 usually I’m a night owl but this long travel day had me wiped out Day 1 at sevenstarsresort was spent getting settled into my room, exploring the property / hanging by the pool and then ending the evening with a wine tasting and sunset dinner at their on-site restaurants 📍 sevenstarsresort bluewhalepr #TurksAndCaicos #SevenStarsHotel #CaribbeanTrip #CaribbeanVacation #TurksAndCaicos #CaribbeanTravel #SummerBucketlist #IslandTravel 2025-09-02 23:45:39 Spend a travel da.. 0 - 12 -51%
August, you were fun but went by way too fast 🙌🏻 swipe for my favorite bites in Chicago this month that deserved a permanent spot on the feed 🍣🥙🍰 2025-08-31 23:14:16 August, yo.. 0 - 39 +59%
No pumpkin spiced lattes in August, please ✋🏻 This is my favorite cozy corner along the Chicago River where N/S meets E/W 💐 #rivernorthchicago #chicagoriverwalk #thingstodoinchicago #ChicagoSkyline #chicago #chicagolifestyle #chicagolife #chicagocreator #chicagotravel #visitchicago 2025-08-30 23:36:40 No pumpkin spiced.. 0 - 16 -35%
Cotton candy skies (and cocktails) 🍭🍒💓🥥 The most delicious apps + noodles from thefarmongracebay in Turks & Caicos 📍 sevenstarsresort bluewhalepr 2025-08-29 23:42:44 Cotton can.. 0 - 30 +23%
On Do Not Disturb 🌞 #TurksAndCaicos #SevenStarsHotel #CaribbeanTrip #CaribbeanVacation #TurksAndCaicos #CaribbeanTravel #SummerBucketlist #IslandTravel 2025-08-28 02:19:47 On Do Not Disturb 🌞 #.. 0 - 23 -6%
Pack with me for Turks & Caicos! 👙😎👗👛 Here are some of my favorite brands that I brought with me on this trip: Dresses: flyingtomato_official patbo tiare_hawaii Athleisure: fabletics #FableticsPartner Skincare: rocskincare fountsociety Swim: michaelkors amazon Sunnies: tjmaxx mokka.studio #packwithme #turksandcaicosislands #turksandcaicos #packingtips #packinghacks #packingvideo #vacationinspiration #vacationoutfits 2025-08-26 23:17:52 Pack with me .. 0 - 21 -14%
Find me at the beach 💦🌴🐚 took a much needed break away from the city at sevenstarsresort in Turks & Caicos. I’ve stayed at this property before and it’s easily one of my favorite resort destinations. I was excited to be back for a days to just turn off my brain, eat all the food and soak in all the Vitamin D as summer comes to a close. 2025-08-25 22:41:41 Find me at t.. 0 - 48 +96%
The tea was spilled 🫖 but our glasses stayed full with drinkgoodtwin 🥐🍓🥂🍋🧺 We still have one full month left of summer so let this be your sign to get out to the lake while it still looks like this! #chicago #chicagobeaches #chicagosummer #chicagogram #visitchicago #chicagotravel #thingstodoinchicago #chicagolife 2025-08-21 20:14:47 The tea.. 0 - 30 +23%
Let this be your sign to visit djsgreatroom in River North. The ambiance and service were wonderful but the food really stole the show. Some of our favorites were the Fish & Chips and the Roasted Greek Half Chicken and you have to save room for dessert because the Warm Skillet Cookie is not to be missed! DJ’s also has a Happy Hour M-F from 4-6pm with both drink and food options! 📍 djsgreatroom in River North, Chicago #chicagofoodie #chicagorestaurants #chicagodining #chicagoeats #downtownchicago #chicagofood #chicagorestaurants #chicagohappyhour #rivernorthchicago #chifoodie 2025-08-20 22:16:47 Let this be your sig.. 0 - 28 +14%
It’s Air & Water Show weekend in Chicago! #chicago #airandwatershow #chicagotravel #visitchicago #chicagocubs #chicagosummer 2025-08-16 03:53:05 It’s Air & Water Show w.. 0 - 18 -26%
Shops in Frankfort, Illinois that are worth making the drive for! Frankfort is less than an hour drive from downtown Chicago which is less than many other Chicago suburb locations. I can’t believe I’ve lived in Chicago for so long but had never visited here before. Be sure to save this list for your next trip out of the city when you visit Frankfort: whimsy.fancygoods hammarsthisandthat theloftfrankfort jollygiraffebooks 📍 Frankfort, IL #chicagosouthland #ChicagoSuburbs #ChicagoTravel #VisitChicago #Frankfort #FrankfortIllinois #chicagoshopping 2025-08-14 23:18:25 Shops in Frankfort.. 0 - 13 -47%
I’ve loved gene_georgetti as a dinner spot in Chicago for years but I just tried their brunch menu for the first time over the weekend and loved it. Everything we had was so good but my favorite dish was the classic Steak & Eggs. Plus they have a Build Your Own Bellini if you’re looking to add bubbles to your brunch 🥂 📍 Gene & Georgetti in River North, Chicago #chicagofoodie #chicagorestaurants #chicagodining #chicagoeats #downtownchicago #chicagofood #chicagorestaurants #chicagohappyhour #rivernorthchicago #chifoodie 2025-08-12 23:06:16 I’ve loved gene.. 0 - 39 +59%
Fully enjoying this August heatwave we’re having in Chicago before it’s gone ☀️🛥️ 2025-08-11 23:47:18 Fully enjoyi.. 0 - 45 +84%
📍 Praia Do Marinha, Portugal Wearing cocopinasd #Portugal #PortugalTravel #VisitPortugal #Algarve #AlgarvePortugal #AlgarveCoast #TheAlgarve #EuropeanSummer #VisitEurope #EuropeExplorer #Portugal #TheAlgarveCoast 2025-08-09 22:10:43 📍 Praia Do Marinha, Po.. 0 - 20 -18%

On average, Jen Chicago Travel Lifestyle gets 0 likes and 24 comments per post. (Historical)

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Trends for likes, comments, and caption length from the last 30 posts.

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