A Chicago Honeymoon for City-Loving Couples

A thriving food scene and gorgeous summers on the lake await honeymooners.
Chicago's elevated trains from the footbridge between Adams and Wabash
Photo: Kenny McCartney
Jessica Kelly
by Jessica Kelly
Updated Apr 29, 2024
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Thinking about a Chicago honeymoon? Romantic, beachside vacations might be the norm for most honeymooners, but other couples might want a slice of something else—like a US honeymoon destination in a bustling metropolis.

Maybe you and your partner prefer exploring new cities, architecture, food markets and street art over the monotony of sitting on a beach. To each their own. For these couples, a honeymoon in Chicago is a great option. The city is nestled into Lake Michigan, where you can see parks, skyscrapers, neo-gothic architecture and find plenty of romantic things to do.

Not only is there a lot to do on a Chicago honeymoon, but you're not dealing with layovers and long flights. With it being in the Midwest, it's a quick flight from the East Coast, and about a four-hour flight from the West Coast.

Ready to start planning your honeymoon? Read on for expert advice on how to create the ultimate itinerary for your Chicago honeymoon.

Chicago Honeymoon Tips in this Article:

Illuminated sign on the Chicago Theater, Chicago, Illinois
Photo: Fraser Hall | Getty

    Best Time to Honeymoon in Chicago

    Before heading anywhere, it's worth looking into the local weather for your months of interest. Visitors must be aware of the frigid temperatures that hit Chicago in the winters. However, you'll find the best weather during the months of April, May, September and October.

    Best weather: May to October.
    Festival highlights: The Chicago Blues Festival (June) and the Chicago Jazz Festival (August) attract music lovers from all over, while Taste of Chicago (September) provides a feast for food enthusiasts.

    Chicago Honeymoon Planning Tips

    It might not be the typical beach destination you may initially think of for a honeymoon, but there's a lot of sightseeing, walking, and plenty of deep-dish pizza to break your wedding diet with.

    It's a great honeymoon option for couples who love big cities. It's really walkable and easy to explore, with incredible Chicago restaurants, and it has a really easy-to-navigate public transportation system.

    Entry requirements: You won't need your passport, but bring your IDs.
    Location: Chicago is located in the northeastern part of Illinois, along the southwestern shores of Lake Michigan.
    Currency: USD.
    Flight time to Destination: From New York, flights to Chicago are around 2.5 hours. From Miami or Los Angeles, they're around 3 or 4 hours.
    Getting around: Chicago has a comprehensive public transportation system, including buses and the elevated train system known as the 'L'. Taxis and rideshare services are also available. For a more scenic mode of transport, consider renting bicycles to explore the extensive network of bike paths along the lakefront and throughout the city.

    Pro tip: Thinking of consulting a honeymoon planning expert? Browse travel agents near you on The Knot Marketplace for Chicago honeymoon expertise, reviews, testimonials and more.

    Best Chicago Honeymoon Hotels

    Chicago hotels can offer quite a few honeymoon packages for newlyweds looking to explore the city. The Four Seasons Hotel Chicago, for example, offers honeymoon packages including spa treatments, craft cocktails and specialty services.

    There are adults-only pools available, in addition to private tour guides, to experience the city's history and music scene. Independent couples can also craft their own Chicago honeymoon package or explore other all-inclusive services with the assistance of sites like TripAdvisor.

    Buckingham Fountain and Cityscape, Chicago, USA
    Photo: Comezora | Getty

    The Peninsula Chicago

    The Peninsula Chicago is right near the Magnificent Mile shopping area, in addition to some of the best entertainment in the area like museums and high end restaurants. At the hotel, guests can enjoy spa treatments, soaking tubs, or take a dip in their swimming pool overlooking the city skyline in the evening.

    5.0 Star Rating | Read Reviews

    Four Seasons Hotel Chicago

    The Four Seasons has a reputation for a reason, so if guests are looking to splurge on high end service, incredible drinks and food right in the hotel, and luxury accommodations, The Four Seasons is a wonderful option. It's located near the Magnificent Mile, in the heart of the city, and offers stunning skyline views.

    5.0 Star Rating | Read Reviews

    Waldorf Astoria Chicago

    If you're looking for a European style Château hotel, the Waldorf Astoria is a great option. Their guest rooms include private balconies, or romantic fireplaces to relax by. They have amenities for guests like spa treatments, pilates, and even complementary transportation within a certain range from the Waldorf Astoria.

    4.5 Star Rating | Read Reviews

    Nobu Hotel Chicago

    Nobu Hotel has 115 rooms and suites available with "old world Japanese influences," in addition to some modern tweaks. They have a great fitness studio, a tranquility pool, views of the skyline, and of course, you can eat and drink at Nobu Chicago which is a fantastic place to indulge in sushi and a really good lychee martini.

    4.5 Star Rating | Read Reviews

    Pro tip: If you're looking for Chicago accommodations that may provide more affordability, privacy or a unique setting, consider staying at a romantic Airbnb or VRBO.

    Chicago Honeymoon Itinerary Ideas

    Chicago is filled with romantic possibilities for honeymooners, whatever your interests may be. From indulging in couples' massages at your hotel to site-seeing and dining out, here are our top recommendations.

    Navy Pier Park at dusk
    Photo: Bob Krist | Getty

    Navy Pier

    Navy Pier is a must, especially if it's your first time in Chicago. You and your new spouse can take a ride on the Centennial Wheel or a spin on the swings. Walk around the area to discover plenty of public art or grab a beer at a nearby restaurant in between the entertainment. The rides give you incredible views of Lake Michigan.

    Millennium Park

    Millennium Park is where you'll find the famous Bean statue (aka Cloud Gate) designed by Anish Kapoor to take pictures with. It makes for a fun photo opportunity and you can see the city skyline reflected in the bean, as well, before walking around the rest of the park.

    John Hancock Building-Tilt

    Most visitors tend to flock to the 103rd floor of Willis Tower to take that infamous photo on the skydeck overlooking the city. That said, sometimes the line for the skydeck can be incredibly long, so there's an alternative that not as many people know about. Head over to the John Hancock building where you'll find Tilt, 360 Chicago. From 1000 feet up, you'll stand in a window located on the 94th floor of the building, where it pushes out, and tilts the window giving the rider amazing views of the city.

    Catch a Game at Wrigley Field

    If sports is something you bonded over as a couple, head over to Wrigley Field for a tour of the arena or a game if it's during baseball season. If it is off-season, tours will often take you down to the Cubs dugout where there's even a Maker's Mark barrel room for a special experience.

    Magnificent Mile

    If you enjoy shopping and dining, the Magnificent Mile is full of stores, restaurants, markets, and bars to explore and maybe splurge on a little something during your honeymoon. The mile is also home to some of the most iconic buildings in the city skyline, in addition to the high end shops and outlets.

    Indulge in Local Restaurants

    Chicago has an incredible food scene, with a variety of sweets, deep dish pizzas, and great cocktail bars. When you're looking to try deep dish, the top hitters are Lou Malnati's or Giordano's. You really can't go wrong with either, but frequent visitors and locals will argue that you should check Pequod's Pizza for an incredible deep dish experience. In addition to deep dish pizza, grab a Chicago dog from Portillo's covered in peppers, celery salt, relish, mustard, tomatoes, onions, and pickle. Head over to BomboBar to try their bombo bombs (like a donut). The Basement is a great spot for drinks and check out Green Street Meats for delicious BBQ.

    Chicago's Beaches

    If you're visiting Chicago during the warmer months, they surprisingly have some really beautiful beaches on Lake Michigan. With skyscrapers in the background, you can relax in the warm sand, take a dip in the water, or rent kayaks, jet skis, paddle boards, and more. A great one to start at is North Avenue Beach, one of the most popular in the area. If you're looking to hop around, check out Oak Street Beach or Loyola Beach, as well.

    Pro tip: Add Chicago honeymoon experiences to your gift registry if you'd like your friends and family to contribute to your romantic getaway. Don't forget to upload a few honeymoon snaps to your wedding website so everyone can keep up with how you're doing on your trip.

    What to Pack for a Chicago Honeymoon

    Marshall Suloway Bridge
    Photo: Joe Daniel Price | Getty

    When you're traveling within the mainland of the US, you don't have to worry about anything like submitting travel documents and vaccination cards, or obtaining a visa. When packing your honeymoon luggage, it all depends on the time of year you're visiting. If you decide to go during the winter, make sure you have a really warm jacket, hat, gloves, thick socks, and good boots.

    If you're there in the summer or the fall, include a few sweaters and walking clothes on your packing checklist. You'll want to include sneakers, athleisure and a nice outfit or two for fancier dinners. Don't forget to pack a towel or swimsuit if you're heading to the beach, as well as sunscreen and some shirts.

    Brittany Barber contributed to this article.

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