• Skip to primary navigation
  • Skip to main content
  • Skip to footer

ORDER YOUR COPY OF THE 2025 JOHN CAIN MAGAZINE

John Cain Photography  |  Dallas TX

John Cain Photography | Dallas TX

  • John Cain Photography
  • Why John Cain?
  • About
  • Services
  • Portfolio
  • The Mag
  • Blog
  • Inquire
MENUMENU
  • Home
  • Weddings
    • At Home
        • A Charming Southern Garden Wedding for Mr. & Mrs. Dunn

          A Charming Southern Garden Wedding for Mr. & Mrs. Dunn

        • Mary and Preston’s Garden Party At-Home

          Mary and Preston’s Garden Party At-Home

        • An At-Home Celebration for Avery and Austin

          An At-Home Celebration for Avery and Austin

    • Ballroom
        • Forever Began in Fort Worth for Caroline & Will

          Forever Began in Fort Worth for Caroline & Will

        • Love in Bloom at the Las Colinas Resort

          Love in Bloom at the Las Colinas Resort

        • A Timeless Texas Wedding: Celebrating Ali and Alex’s Love in the Hill Country

          A Timeless Texas Wedding: Celebrating Ali and Alex’s Love in the Hill Country

    • Country Club
        • Built to Last with Mr. & Mrs. Spradley

          Built to Last with Mr. & Mrs. Spradley

        • Celebrating the Cohns at Brook Hollow Golf Club

          Celebrating the Cohns at Brook Hollow Golf Club

        • Mr. and Mrs. McKenna Married in Dallas

          Mr. and Mrs. McKenna Married in Dallas

    • Tented
        • A Colorful Ranch Wedding in Celebration of the Conolys

          A Colorful Ranch Wedding in Celebration of the Conolys

        • Lake Countryside Meets Secret Garden

          Lake Countryside Meets Secret Garden

        • The Wilsons’ Wedding Day at Arlington Hall

          The Wilsons’ Wedding Day at Arlington Hall

    • Bridal Portraits
        • Whitney’s Bridal Portraits

          Whitney’s Bridal Portraits

        • Haylie’s Dream Dress Inspired by Texas Wildflowers

          Haylie’s Dream Dress Inspired by Texas Wildflowers

        • Radiant in Reem Acra with Mrs. Butkus

          Radiant in Reem Acra with Mrs. Butkus

    • Engagement Portraits
        • Sundown on the Ranch with the Future Sartors

          Sundown on the Ranch with the Future Sartors

        • Counting Down to Wedding Day with Elizabeth & Robert

          Counting Down to Wedding Day with Elizabeth & Robert

        • Clara & Blake’s Story of Connection and Perfect Timing

          Clara & Blake’s Story of Connection and Perfect Timing

  • Destinations
    • Beaches
        • Back to the Bay Area

          Back to the Bay Area

        • Night One in Napa: The Matthews’ Rehearsal Dinner

          Night One in Napa: The Matthews’ Rehearsal Dinner

        • Caroline and Matthew’s Garden-Themed Rehearsal Dinner in California

          Caroline and Matthew’s Garden-Themed Rehearsal Dinner in California

    • Mountains
        • MADELEINE MORREN + ETHAN ELIZONDO WEDDING

          MADELEINE MORREN + ETHAN ELIZONDO WEDDING

        • A Ceremony Overlooking the Mountains of Colorado with Mr. & Mrs. Lapke

          A Ceremony Overlooking the Mountains of Colorado with Mr. & Mrs. Lapke

        • Up in the Mountains of Colorado with Mr. & Mrs. Duwe

          Up in the Mountains of Colorado with Mr. & Mrs. Duwe

    • Texas
        • SAVANNAH TROUTT & BEN STUBBS

          SAVANNAH TROUTT & BEN STUBBS

        • CARILYNN PEYTON + BEN BAXTER WEDDING

          CARILYNN PEYTON + BEN BAXTER WEDDING

        • ABBEY STOKER + HUDSON HARRISON WEDDING

          ABBEY STOKER + HUDSON HARRISON WEDDING

  • Inspiration
    • Behind The Scenes
        • Spring Cake Inspiration

          Spring Cake Inspiration

        • Get to Know Designs By Andrea

          Get to Know Designs By Andrea

        • Engagements in Florida with the future Mr. & Mrs. Hendrie

          Engagements in Florida with the future Mr. & Mrs. Hendrie

    • Fashion
        • Outfit Inspiration From Style Icon Kate Middleton

          Outfit Inspiration From Style Icon Kate Middleton

        • Outfit Inspiration From Style Icon Grace Kelly

          Outfit Inspiration From Style Icon Grace Kelly

        • Things We’re Loving: Mismatched Bridesmaids Dresses

          Things We’re Loving: Mismatched Bridesmaids Dresses

    • Registry
        • Step Inside Blue Print’s Annual Something Blue Spring Social

          Step Inside Blue Print’s Annual Something Blue Spring Social

        • Registry Items I Actually Love… and the Items I Could Have Gone Without!

          Registry Items I Actually Love… and the Items I Could Have Gone Without!

        • A Mother’s Day Gathering in the Garden with Juliska

          A Mother’s Day Gathering in the Garden with Juliska

    • Entertaining
        • A Poolside Pink Party for Haylie Jackson

          A Poolside Pink Party for Haylie Jackson

        • Spring Soireés Are Here to Stay!

          Spring Soireés Are Here to Stay!

        • Cocktails & Canapés for an Evening at the Rosewood Mansion

          Cocktails & Canapés for an Evening at the Rosewood Mansion

    • Travel
        • A Stroll through New York City with Emily and Will

          A Stroll through New York City with Emily and Will

        • A Few of Our Favorite Things in Lake Como, Italy

          A Few of Our Favorite Things in Lake Como, Italy

        • Romantic Guide to Nantucket

          Romantic Guide to Nantucket

All, Lifestyle, Weddings

Romantic Guide to the Windy City

By:

John Cain Sargent

View Full Gallery Scroll Through Images

Earlier this summer, in the peak of June when triple digits blazed in Dallas, I escaped to the perfectly cool Windy City for Kelly & Alex’s engagement portraits. Before leaving for the trip, John Philp Thompson shared an impressive Chi Town guide with me. My only regret: only making it to the first rec, Au Cheval. John Philp was absolutely right, the burger was the best I’ve ever enjoyed. My refuel was cut short, however, as it was time for me to meet Kelly and Alex for portraits at the Caldwell Lily Pool in Lincoln Park. The park has perfect footpaths and allowed us to walk to the spot Alex Proposed just outside the Chicago Zoo. (Sidenote—without the animals, you may not notice you are even in the Chicago Zoo because it’s so deceitfully and beautifully woven into the cityscape.) We ended portraits on the water at Lake Michigan before I caught a taxi back to the airport.

The trip was too short! I love how Kelly and Alex incorporated Chicago, the place they met, into their engagement portrait story. They have since moved to D.C. but our team looks forward to their Dallas wedding come December. Kelly and Alex, thank you for sharing Chicago with me! Wedding day will be here before you know it.

I hope you find yourself planning a trip to Chicago here soon so you can take JPT’s guide with you. If all his recommendations are in line with Au Cheval’s burger, I am confident you will be steered in the right direction!

DINE

BEST PIZZA

Lou Malnati’s is my favorite “tourist-y” Chicago deep dish. . . but the locals go to Peaquod’s for a bit better deep dish

BEST CHICAGO ‘STAPLE’

Stephanie Izard’s The Girl and the Goat, but she has two newer restaurants called Little Goat Diner and Duck Duck Goat

BEST BURGER

Au Cheval—expect a wait. There are a ton cocktail bars, Soho House, and cool restaurants all around so when they say “3-hour wait”, go have some drinks!

BEST SANDWICH

Publican Quality Meats

BEST BBQ

Green Street Smoked Meats

BEST MEDITERRANEAN

Avec, but ēma is a close second.

BEST TACOS

Big Star or Antique Taco, both located in Wicker Park.

BEST “BRUNCHING”

Bongo Room is a staple and indulgence, but Summer House Santa Monica or Beatrix are pretty great too.

BEST DONUTS

Stan’s or Donut Vault.

BEST COCKTAILS

DrumBar  Violet Hour, Maude’s Liquor Bar, Lost Lake, & Scoffloaw

OTHER NOTABLES

  • Lonesome Rose – TexMex in Logan Square
  • Mott Street  – Asian Fusion in Wicker Park
  • Monte Verde – Italian in West Loop
  • Fat Rice – Macanese
  • Parachute
  • Giant

DO

MILLENNIUM PARK

The Bean, Jay Pritzker Pavilion, Laurie Gardens

MAGNIFICENT MILE

A great few blocks of shopping along Michigan Ave.

ARCHITECTURE BOAT TOUR

Sounds dorky and touristy, but actually pretty awesome. This one is my favorite. Worst comes to worst, there’s a bar on board..

JOHN HANCOCK OBSERVATION DECK (SIGNATURE ROOM ON THE 96TH FLOOR)

Awesome views during the day — I wouldn’t pay to go to the top of Sears “willis” tower and do the Skydeck.. the views are better at John Hancock and free. Pro Tip: The drinks are expensive (and not the best) at the Signature Room, but worth going for a table and go take photos out the windows.. don’t order. Get up and leave before you order. My favorite cocktail bar is DrumBar at the top of a boutique hotel a block away!

LAKESHORE TRAIL

Run/bike/walk!

Thank you for all the amazing suggestions, John Philp! Check out more city guides from the Risky Jackal here. 

Tags

Engagements Romantic Guide Travel

« Previous Post
Next Post »

Reader Interactions

Comments

Cancel reply

Your email address will not be published. Required fields are marked *

Explore More

  • A Heavenly Evening at the DCC
    Weddings September 13, 2021

    A Heavenly Evening at the DCC

  • A Night with Jordan Kahn and Company at the Ritz-Carlton
    Weddings March 24, 2021

    A Night with Jordan Kahn and Company at the Ritz-Carlton

  • PAIGE + WILLIAM’S REHEARSAL DINNER
    Weddings March 19, 2025

    PAIGE + WILLIAM’S REHEARSAL DINNER

  • Our Favorite Kiss in the Aisle Moments
    Weddings April 24, 2020

    Our Favorite Kiss in the Aisle Moments

  • Getting Married in Style with  Kay and Stuart
    Weddings January 15, 2021

    Getting Married in Style with Kay and Stuart

  • Sundown on the Ranch with the Future Sartors
    Weddings June 25, 2024

    Sundown on the Ranch with the Future Sartors

  • Herend’s Chinese Bouquet Creates an Idyllic Fall Tablescape
    Weddings October 25, 2019

    Herend’s Chinese Bouquet Creates an Idyllic Fall Tablescape

  • Cocktails & Canapés for an Evening at the Rosewood Mansion
    Weddings March 26, 2024

    Cocktails & Canapés for an Evening at the Rosewood Mansion

  • Megan and Caleb’s Timeless Wedding at the Rosewood Mansion
    Weddings March 21, 2024

    Megan and Caleb’s Timeless Wedding at the Rosewood Mansion

  • A look back at our Social with Diamonds Direct
    Weddings November 17, 2022

    A look back at our Social with Diamonds Direct

  • Italian Influence in Horseshoe Bay for #SuttontoSadau
    Weddings October 6, 2020

    Italian Influence in Horseshoe Bay for #SuttontoSadau

  • Karli Francis & Will Farnsworth
    Weddings March 15, 2023

    Karli Francis & Will Farnsworth

@johncainphotography

Footer

Get In Touch

214.520.6771

studio@johncainphotography.com

4623 W Lovers Lane

Dallas, TX 75209

© 2020 – John Cain Photography

John Cain Photography

  • Services
  • About
  • Portfolio
  • As Seen In
  • Inquire

Blog

  • Weddings
  • Lifestyle
  • Destinations
  • Facebook
  • Instagram
  • Pinterest
  • Spotify