Discover Chicago for Your Honeymoon: The Heart of the Midwest with Big City Energy

Overview

Romantic honeymoon destination combining Midwest charm and big-city energy
Stroll hand-in-hand along Lake Michigan or take a Chicago River architecture cruise
Enjoy world-class dining, museums, live jazz, and skyline views
Choose from top IHG Hotels & Resorts for luxury, boutique, or budget-friendly stays
Explore in any season—spring blooms, summer festivals, fall colors, or cozy winter vibes
Inclusive and welcoming with a vibrant LGBTQ+ scene in Northalsted (Boystown)

Why Honeymoon in Chicago?

If you’re dreaming of a honeymoon that mixes world-class food, iconic architecture, and romantic city vibes, then Chicago might just be your perfect match. Whether you’re cruising down the Chicago River, cuddling under twinkling skyline lights, or savoring deep-dish pizza after a museum date, this city brings the magic. IHG Hotels and Resorts‘ portfolio comprises over 6,700 properties around the globe, including many domestic destinations. When you’re planning your honeymoon, you can find a property that’s perfect for a couples retreat.

Chicago blends old-school charm with modern excitement. It’s a city made for strolling hand-in-hand along Lake Michigan, catching live jazz in a cozy bar, or riding the Ferris wheel at Navy Pier. It’s big enough to explore something new every day, yet intimate enough to feel personal.

Weather in Chicago

Chicago experiences four distinct seasons. Spring (April to June) and fall (September to October) are ideal for honeymoons—think mild temps, blooming parks, and fewer crowds. Summers are sunny and lively, perfect for lakefront picnics. Winters are chilly but romantic, with snow-dusted streets and festive lights (if you’re into that cozy, cuddle-up vibe).

Getting to Chicago

Chicago is a major hub with two international airports—O’Hare (ORD) and Midway (MDW)—making it easy to fly in from anywhere.

Sample flight costs (round-trip economy):

New York (JFK) to Chicago (ORD): $120–$250
Los Angeles (LAX) to Chicago (ORD): $180–$300
Miami (MIA) to Chicago (ORD): $140–$280

InterContinental Chicago Magnificent Mile

Where to Stay: IHG Hotels & Resorts for Honeymoons in Chicago

Here are some of the top IHG Hotels & Resorts for Honeymooners in Chicago:

InterContinental Chicago Magnificent Mile – This historic hotel feels like a blend of European luxury and downtown Chicago energy. Enjoy lake views, a Roman-style pool, and walkability to top attractions. Rates from $280/night.

Kimpton Gray Hotel – For couples who love design, this sleek, art deco-inspired hotel is full of personality and perfect for city lovers. It’s only blocks away from Millennium Park, restaurants and museums. Rates from $230/night.

Hotel Indigo Chicago Downtown Vernon Hills – A boutique vibe in Vernon Hill’s, one of the city’s most charming neighborhoods. Think tree-lined streets, cute cafes, and just enough distance from downtown buzz. The hotel features spacious rooms with modern décor, an indoor pool, a fitness center, and an on-site restaurant and bar for easy dining. Rates from $190/night.

Holiday Inn & Suites Chicago-Downtown – Spacious rooms and great value, located near Union Station and the West Loop food scene. Guests enjoy an on-site rooftop pool and easy access to public transit. Rates from $160/night.

Plus, the IHG One Rewards program is an easy way to earn points toward free nights. The program has lots of valuable perks, like 15% off award nights at new properties and a fourth night free on award stays for select IHG cardholders. You can join One Rewards for free with just a few clicks.

Things to Do on Your Chicago Honeymoon

Take a River Architecture Cruise
It’s touristy, but worth it. Glide through the city’s canyons of skyscrapers and learn about the stunning architecture from the water.

Explore Millennium Park & the Art Institute
Snap a photo at “The Bean,” stroll through Lurie Garden, then wander through the Art Institute for world-class art (and air-conditioning).

Indulge in the Food Scene
From Michelin-starred restaurants to hot dog stands, Chicago’s food game is strong. Book a romantic dinner at a rooftop spot or taste-test your way through West Loop’s “Restaurant Row.”

Catch a Live Show
See a Broadway-caliber musical, a comedy act at Second City, or a symphony performance. There’s something happening every night.

Day Trip to the Lake or Wicker Park
Rent bikes and cruise the lakefront trail or spend the afternoon boutique-hopping and sipping coffee in artsy Wicker Park.

LGBTQ+ Friendly

Chicago is a proudly inclusive city with a vibrant LGBTQ+ scene. The Boystown neighborhood (now officially called Northalsted) offers bars, events, and a welcoming vibe for all couples.

Final Thoughts

Chicago offers honeymooners a romantic, exciting escape that’s equal parts culture, comfort, and connection. Whether you’re toasting on a rooftop or holding hands along the lake, this city delivers unforgettable moments—without the long-haul flight. And with Honeyfund, your guests can help you experience it all.