Planning a city break to Chicago? It’s a great choice, one of the most exciting and romantic cities in the U.S. But like any major city, where you stay can shape your entire experience, so we have highlighted the areas in Chicago where, depending on your preferences, we think you will enjoy the best.
Whether you’re dreaming of luxury lake views, buzzy rooftop bars, historic architecture, or neighbourhood charm, Chicago offers something for every kind of city traveller. Here’s our Awesome Travel Holidays guide to the best areas to stay in Chicago – curated for couples looking to enjoy a short but memorable stay in the ‘Windy City’.
🌆 1. Best for First – Time Visitors and Iconic Views: The Loop
This is the heart of downtown Chicago, home to iconic sights like Millennium Park, Cloud Gate (The Bean), the Art Institute of Chicago, and the stunning Chicago Riverwalk.
Why stay here?
- Central to major attractions
- Excellent public transport links
- Ideal for sightseeing and skyline views
Top Hotels in The Loop:
- 🛏️ LondonHouse Chicago – Glamorous rooftop bar and river views
- 🛏️ JW Marriott Chicago – Elegant and centrally located
- 🛏️ Nobu Hotel Chicago – Stylish design, iconic cuisine
🛍️ 2. Best for Trendy Vibes & Foodie Finds: River North
Just north of The Loop, River North is a vibrant, artsy neighbourhood full of design studios, independent galleries, and some of the best dining in the city.
Why stay here?
- Chic restaurants and rooftop lounges
- Walking distance to the Magnificent Mile and Navy Pier
- Boutique hotel options
Top Hotels in River North:
- 🛏️ Kinzie Hotel – Stylish, central, and great value.
- 🛏️ 21c Museum Hotel Chicago – Boutique hotel-meets-modern art gallery
- 🛏️ The Westin Chicago River North – Upscale comfort with river views.
🏞️ 3. Best for Lakefront Luxury & Easy Sightseeing: Streeterville
Tucked between Lake Michigan and the river, Streeterville is ideal for couples wanting a romantic lakeside feel, with easy access to top attractions.
Why stay here?
- Close to Navy Pier, Ohio Street Beach & Magnificent Mile
- Lakeside walks and great city views
- Luxury hotels and spa options
Top Hotels in Streeterville:
- 🛏️ Loews Chicago Hotel – Rooftop terrace with lake views
- 🛏️ Riu Plaza Chicago – Sleek, modern & great location
- 🛏️ Hotel EMC2, Autograph Collection – Artistic, modern and romantic
🖼️ 4.Best for Upscale Romance and Quiet Nights: Gold Coast
This historic and refined area just north of downtown offers a quieter pace without sacrificing charm or luxury. Think leafy streets, boutique shops, and candle-lit bistros.
Why stay here?
- Peaceful, elegant atmosphere
- Upscale dining and boutique shopping
- Close to Oak Street Beach and Lincoln Park
Top Hotels in the Gold Coast:
- 🛏️ Viceroy Chicago – Chic rooftop pool and luxury finish
- 🛏️ Thompson Chicago – Stylish and contemporary
- 🛏️ The Ambassador Chicago – Classic elegance in a beautiful building
🌿 5.Best for Local Living and a Leafy Escape: Lincoln Park
For those wanting a more relaxed, local feel, Lincoln Park is a residential gem. It’s known for its parklands, Victorian homes, and charming vibe.
Why stay here?
- Free attractions like Lincoln Park Zoo and Conservatory
- Lovely for morning walks and picnics
- Friendly cafés and boutique shopping
Top Hotels in Lincoln Park:
- 🛏️ Hotel Lincoln – Hip boutique hotel with park views
- 🛏️ Villa D’Citta – Romantic, Italian-style guesthouse
- 🛏️ The Sono Chicago – Intimate and stylish B&B
🏟️ 6. Best for Sports Fans & Casual Vibes: Wrigleyville
If you love live sports and a lively neighbourhood scene, Wrigleyville offers a fun, easy-going base centred around the iconic Wrigley Field.
Why stay here?
- Catch a Chicago Cubs game
- Enjoy bars, local music, and a community vibe
- Easy access to downtown via the L train
Top Hotels in Wrigleyville:
- 🛏️ Hotel Zachary – Steps from Wrigley Field, with style and substance
- 🛏️ Majestic Hotel Chicago – Classic boutique with charm
- 🛏️ The Wheelhouse Hotel – Sporty-chic with bold design touches
💬 So… Where Should You Stay?
Looking for convenience and sightseeing? Try The Loop or River North. Want romantic vibes and peaceful strolls? opt for Gold Coast or Streeterville. Prefer a more local or sporty feel? Lincoln Park or Wrigleyville might be perfect.
Wherever you choose, at Awesome Travel Holidays, we’ll tailor your hotel stay to suit your travel style, pace, and budget.
🚀 Thinking about a Chicago city break? Let’s make it an Awesome Travel Experience!
Awesome Travel Holidays
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Other travel guides in our USA series include:
