Three Interesting Chicago Date Ideas for History Buffs

Valentine’s Day is nigh, so we have three Chicago date ideas for people who find romance amidst the city’s history and architecture. These activities and locations provide the perfect setting for a date night, while also indulging our passion for Chicago’s past.

#1. Our Date Night Historic Walking Bar Tour on 2/15

The Court of Lions is one of the highlights of the Date Night Historic Walking Bar Tour. Photo by Pawel Skrabacz.

Nothing’s more romantic than hearing stories about billy goats and gangsters, right? Certainly makes our hearts flutter!

The mostly-indoor Historic Walking Bar Tour should be on any list of Chicago date ideas regardless of the season. It combines three rounds of drinks and snacks with stories and beautiful, interesting spaces from the entertainment history of the Mag Mile. This tour is very popular with locals, and couples out on a date night join this tour almost every week, which gave us some inspiration.

This year, we’re taking it up a notch with a special version of the tour on Saturday, February 15th. The tour guide (yours truly) will share some stories we’ve newly researched about the more romantic side of the Mag Mile. Couples will each share a decadent slice of chocolate cake near the tour’s conclusion, in a gorgeous hidden space within a Jazz Age skyscraper. Hope to see you on the 15th!

#2. An Afternoon at the Chicago History Museum

Chicago history museum jazz club date idea
See, visiting the history museum is just like going to a live jazz club for your date! Photo by Marcin Wichary vis flickr.

Don’t let anyone tell you that a trip to the museum cannot be romantic! The Chicago History Museum is, of course, a wonderful research institution and their permanent exhibit “Crossroads of America” is great. Marveling at the artifacts on display there, along with their current “Modern by Design” special exhibit, should be on your Chicago date ideas list because it allows so much freedom. There can be a lot of pressure during date, especially in the early stages. The scope and size of the exhibits will give you plenty of material to chat about.

The History Museum’s location helps its status as a date destination. The Old Town entertainment district is just blocks away on Wells Street. You can grab dinner, drinks or see a Second City show. A solid one-two punch amongst Chicago date ideas.

#3. Drinks at LondonHouse Rooftop

LondonHouse Chicago skyline date ideas Chicago
The LondonHouse’s rooftop, dead center in this photo, offers sweeping romantic views of the city. Photo by Pawel Skrabacz.

As we have covered before, rooftop bars have cemented themselves among Chicago’s best date ideas. There’s a lot of competition in this field, but we’d wager that a Valentine’s date night done right should feature the LondonHouse Rooftop. Situated right at the historic heart of the city, the sightlines from the LondonHouse Rooftop are spectacular. You and your paramour can peer straight down the Mag Mile or gaze towards the main branch of the Chicago River backlit by brilliant dusklight.

The LondonHouse offers both drinks and food, of course. Fair warning that the menu’s prices do tend to match the million dollar views. The building has a long history of romantic date nights, to boot. Sadly, there’s not likely to be lovely lounge singers like Sarah Vaughan, which the old London House dinner club once hosted. You can still listen to that stellar music on your way to the date though!

A Tour Is Always One of the Best Chicago Date Ideas!

The Date Night Historic Bar Tour on the 15th is capped at 14 guests and its already filling up fast. Don’t wait too long to reserve a spot.

Can’t make the Date Night Historic Bar Tour? Don’t sweat it–all our walking tours are fun date ideas. I regularly lead couples around town on the Historic Chicago Walking Bar Tour and 1893 World’s Fair Tour. Find a Friday or Saturday that works for your special someone and leave the rest to us.

– Alex Bean, Content Manager and Tour Guide


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Private Tour Coordinator and Tour Guide

There is no shortage of things to discover in Chicago—I love being an urban explorer and uncovering its hidden places. I have an MA in Public History from Loyola University Chicago, and I have worked as a museum educator and kindergarten teacher. My desire to learn new things fuels my passion for educating others, which I get to experience every day as a Chicago tour guide. I live in the northern neighborhood of Rogers Park.

“Our guide Ellen was exceptional and gifted with a great personal touch.”


Tour Guide

Whether you are a first-time visitor or a lifelong resident, the vibrant history and modern majesty of Chicago never ceases to amaze. I’m a graduate of Columbia College with an M.A. in Interdisciplinary Art. I’ve worked for many years as an educator at City Colleges of Chicago. As tour guide at Chicago Detours, I integrate my enthusiasm for culture and architecture with my passion as an educator. West Town/Noble Square area is home for me.

“Jen was a perfect storyteller and kept us spellbound for hours.”


Tour Guide

With our Chicago neighborhoods, vibrant cultural institutions and nearly two centuries of larger-than-life stories, there’s never a dull moment here! I’m a fifth generation Chicagoan and a graduate of Washington University in St. Louis. In addition to guiding tours, I’m a creative writer and amateur genealogist. I also enjoy the city’s dynamic theater scene. You can also read overlooked stories from 19th-century newspapers on my “Second Glance History” blog. I live in River North.


Tour Guide

Chicago is unique as it always evolves into the future while holding on to the past. I’m fascinated by how people latch on to old architecture but happily pave over others. My background is in theater and performance and I’ve been a tour guide here for more than 10 years. Currently I’m finishing my Master’s in Public History at Loyola University because I love to teach the history of this scrappy city. I’m in the Edgewater neighborhood.


Operations Coordinator and Tour Guide

Chicago’s history is so fascinating, you could spend a lifetime uncovering its secrets…I’m willing to give it a try! I have an M.A. in US History from the University of Nevada-Las Vegas and then pursued doctoral studies in Urban History at the University of Illinois at Chicago. I love to learn new aspects of Chicago’s rich history and then share my knowledge as a tour guide with Chicago Detours. I live in Ravenswood.

“Marie was a bubbling fountain of information and contagious enthusiasm.”


Operations Coordinator and Tour Guide

As a fourth generation Chicagoan, I have been living and loving Chicago by bike, on foot, public transit or automobile. I am a graduate of UIC where through the College of Urban Planning and Public Affairs, began my eagerness to understand the nature, history and impacts of urban planning and development. It is incredibly rewarding to give back to this wonderful city by helping out in the office of Chicago Detours. I live in the incredibly diverse neighborhood of Albany Park.
“Sonny was extremely knowledgeable about all things Chi-town.”
Wade K


Content Manager and Tour Guide

Chicago has so many neighborhoods, buildings, and by-ways that it’s hard to go long without seeing something new, or something familiar from a new angle. I studied Cinema History for my M.A. from the University of Chicago. I’ve worked as a culture writer for various publications and as an educator of the humanities at the City Colleges of Chicago. I’m thrilled to share my love of this city’s busy past and unique architectural spaces with Chicago Detours. I live in the Chicago neighborhood of Lincoln Park.

“Alex was fascinating to listen to. He clearly knows his history and it shows.”
Katie K

Amanda Scotese

Executive Director and Tour Guide

I’m an interpreter of personal stories from the past and the city’s landscape. I love to imagine what originally happened inside old unmarked buildings, and what forces have shaped their design. I studied Chicago history, architectural history, and anything Chicago-related through my M.A. in the Humanities at the University of Chicago. My love for stories was enriched by my B.A. in Literature from the University of Michigan. I’ve written travel articles for publications like Rick Steves’ Italy best-selling travel guides, the San Francisco Bay Guardian, and The Chicago Food Encyclopedia. I live in the Chicago neighborhood of West Avondale.
“You can TELL Amanda is hyper-passionate about doing the research and getting the story that nobody’s heard before.”
Shelby F

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