Honeymoon Guide to Chicago

INTRO

Chicago is one of my favorite cities in the world, and I’m so excited to share its more romantic side in this honeymoon guide. While you might only think of sports and deep dish pizza at first mention, there’s also incredible architecture, culture, and entertainment waiting to be discovered. For those wanting more than a beach getaway for their honeymoon, Chicago is an amazing destination I feel passionately about (but there’s also beaches, don’t worry!).

Its location in the middle of the country is a helpful factor, making it easy to visit logistically. You have international and domestic airports and an Amtrak station that links up with many routes. However, despite being the third largest city in the US, I feel like it’s often overlooked. I hope to shed some light on all the unique things you can do in the windy city on a honeymoon.

I’m going to talk about places to stay, where to eat and drink, and what to do with an emphasis on more intimate options for a honeymoon. The first recommendation in each section is the most romantic, in my opinion, but there’s truly something for everyone! There are so many different ways to spend quality time and fall more in love with each other while you fall in love with Chicago.

WHERE TO STAY

A honeymoon is a special trip, and the accommodation should be special, too. The Publishing House Bed and Breakfast is my favorite option for where to stay for a Chicago honeymoon (and it’s female-owned). I mean look at this dreamy bathtub situation! You will feel so pampered here. The rooms are so beautiful, and each one is unique. If this is where you decide to stay, make sure to carve out some time to enjoy the room and rest.

Another highlight is the included breakfast–a rotating menu made fresh-to-order daily with coffee, juices, a fruit station, and more. There’s something so luxurious about starting your day with a relaxing, delicious meal in a gorgeously designed space. Its location near the Fulton Market District will also excite foodies, as Fulton Market is home to a vibrant culinary scene.

Another personally vetted option is The Viceroy Hotel. The rooms are fancy and also offer soaking bathtubs, which is a must for a romantic trip. Did I mention there’s a rooftop pool?! The Viceroy is located in Chicago’s Gold Coast neighborhood, a luxurious area home to the original Playboy Mansion, many fantastic restaurants, and high-end boutiques. Both of these options would be perfect for a Chicago honeymoon.

WHERE TO EAT

You will not want to miss dining at Aba during your honeymoon in Chicago. The atmosphere is enchanting, especially on the rooftop patio– it makes sense why Aba is considered one of the most romantic restaurants in Chicago. The menu is designed around shared plates, so you get to sample amazing Mediterranean dishes in a very intimate way. Make sure you order the brisket hummus! 10/10 food and vibes. If you stay at the Publishing House Bed and Breakfast, you’re only a 15 minute walk away from this incredible dinner spot.

If this honeymoon in Chicago is also your first visit, then I do have to recommend trying deep dish pizza since the city is famous for it. But, honestly, there is some romance in the experience! It takes about 40 minutes to make each pie, so there’s time to have a drink and enjoy each other’s company while you wait. It’s also fun and flirty to watch your partner serve you a slice, with the cheese stretching seductively between you. My favorite spots are Gino’s East, Lou Malnati’s, and Giordano’s.

If you want to go total luxury and treat yourself to an evening of fine-dining, Alinea is a great choice. It’s a three Michelin star restaurant featuring creative, New American plates. Alinea is often on lists for best restaurants in the United States and best restaurants in the world! It would definitely be a night to remember.

WHERE TO DRINK

Let’s talk rooftop bars with iconic Chicago views that would be perfect for a honeymoon drink. Cindy’s Rooftop overlooks “The Bean,” Millennium Park, and Lake Michigan. It’s a super cute bar and is worth popping into before/after a stroll through Millennial Park where you can see Cloud Gate and the Crown Fountain. Then you have the London House rooftop, which puts you in the middle of the city above the Chicago River. Both would be great options for a romantic, sunset drink as you watch the city lights start to flicker on.

Chicago has so many watering holes to choose from, so you’ll be able to find something you both love and/or something new and different. If you’re wanting to get as high up as you can for a drink in the sky, you’ll want to visit CloudBar on the 94th floor of Chicago’s Hancock Tower. I always recommend going way up for a drink whenever you visit a massive city because the views are so impressive from above. Let’s move on to the activities section of this honeymoon guide to Chicago 🙂

WHAT TO DO

For a super romantic spa experience to do during your honeymoon in Chicago, check out Aire Ancient Baths. This place is really special and hard to put into words unless you see the space yourself. There are only two Aires located in the US, the rest are in Europe. You get to spend 90 minutes relaxing in all the different baths and saunas– there’s hot ones, cold ones, baths with jets and waterfalls, a salty bath you can float in, and more! I highly recommend booking a couples massage as well as the bath experience. It’s a staple honeymoon activity in a really unique environment you should not miss.

The rest of your activities will depend on the kind of honeymoon that fits your personalities best. For some adrenaline, check out the new Flyover Experience on Navy Pier and/or The Ledge at Willis Tower. For culture lovers, you have to do a river architecture cruise and check out one of the many museums (The Art Institute of Chicago is my favorite). If you want to see live music, you have Broadway shows, The House of Blues, and Rosa’s Jazz Lounge. Chicago is a city of sports fans, so you should definitely go to a game depending on what seasons you’re there–see The Blackhawks play hockey, The Bulls or The Sky play basketball, The Cubs or Sox play baseball, The Bears play football, or The Fire or The Red Stars play soccer. Let me share more details about some of these options below and give you a beach recommendation, too.

The newest attraction on Chicago’s Navy Pier is called Flyover, and it’s so much fun! I don’t want to spoil the experience, but you get to see Chicago from so many angles through state-of-the-art technology and learn more about its people in the process. It’s kind of like a mash up between an art gallery and a theme park ride. Flyover is another one of those unique experiences that you can only do in a few places in the world, so it’s totally worth checking out and only takes about an hour. It’s also worth strolling along Navy Pier during your honeymoon in Chicago. You can ride the Centennial Wheel, grab a drink at the Offshore Rooftop bar, and do some shopping.

The Ledge at Willis Tower is another fun activity that will get your adrenaline pumping while you take in sweeping views of the city. You may have heard of it before… those glass boxes you stand in that stick out from the side of a skyscraper. It’s definitely scary, especially if you’re afraid of heights! Facing a fear side-by-side will make you feel even closer during your honeymoon in Chicago–not to mention the epic photo op! You’re sure to get in lots of laughs, too, if you book either The Flyover Experience or The Ledge.

The Chicago River runs through out the city, and you can get on the water for a river architecture cruise to take it all in. The architecture cruises are one of those touristy things that locals actually do and love, too, so that says a lot about how good the experience is. The views of the iconic buildings from the water is incredible, but it’s even more fascinating learning about the architecture and history–you can come home with some facts! Chicago is stunning, which is apparent as soon as you visit, but learning about the planning and design of the city brings it all together and makes for a really nice afternoon. My favorite building is the new St. Regis, the tallest building in the world designed by a female architect. You can also buy drinks on board, which makes it even more enjoyable.

If you’re looking for something to do on a more chill day, there’s some really great walking paths in Chicago you could lazily stroll hand-in-hand or utilize to get some exercise in together. Speaking of the river, you have the Chicago Riverwalk, which boasts tons of great drinking and dining options in addition to a nice riverfront path. There’s also a light show on The Mart building each night April-December you can check out if you’re taking an evening stroll. Then you have The 606, which you can think of as Chicago’s version of New York’s High Line. They’ve transformed an abandoned rail line that goes through some of Chicago’s hippest neighborhoods into 2.7 miles of walking and running paths.

There’s definitely so much more to do in Chicago, but the last thing I want to mention in this guide is North Avenue Beach. If you can’t fathom a honeymoon without any beach time, Chicago’s location on Lake Michigan makes that possible, too! North Avenue Beach is a big, wide beach with lots of room to spread out, relax, and swim. You’ll also be close to Shore Club, a beach bar you can stop into for lunch and cocktails, or you can even reserve a cabana and spend the whole day there if you want more of a party vibe. You actually have 20+ beaches to choose from if you decide to plan your honeymoon in Chicago!

CONCLUSION

I hope you found this honeymoon guide to Chicago helpful and feel inspired to consider Chicago for your honeymoon now that you know a bit more about its romantic side. When the heart craves the cultural experiences you get from going abroad, but the budget/ time off work available says you’re staying stateside, Chicago has you covered. You have more options than you could ever get to in one trip, world class dining and hotels, and a perfect mix of relaxing and fun, memory-making activities to choose from.

Don’t forget the top romantic recommendations mentioned in each section: staying at The Publishing House Bed and Breakfast, having dinner at Aba, and booking a massage at Aire Ancient Baths. After that, what you do is icing on the cake, and you can tailor it perfectly for your needs and wants! After the whirlwind of wedding planning and events, your honeymoon is time for just you two–to rest, explore, and deepen your bond in a new place. Chicago will not disappoint!

Make sure to check out the links for everything mentioned above to start the booking process, especially if you are traveling during peak season. And congratulations on tying the knot! I know you will cherish all the memories you make during this season of life, especially those made on a honeymoon in Chicago.

YOU MIGHT ALSO LIKE

If you stumbled upon this honeymoon guide to Chicago and want more of my Chicago content, check out these other posts!

A Chicago Staycation for When You Want to Treat Yo’Self

The Chicago Flyover Experience is now open! Here are my thoughts on Navy Pier’s newest attraction.