Holiday rentals in Soldier Field Sled Hill

The Metropolitan Retreat (2BD / 2BA)

Located at the epicenter of Chicago's cultural, historical, and business attractions, this luxurious 2 bedroom apartment offers guests all the comforts of home, whether on the road for work or play. Within walking distance are world famous attractions including: Millennium Park, The Bean, Navy Pier, Riverwalk, Soldier Field, The Field Museum, and more. Additionally, guests are merely a couple blocks from an "L" train stop, which will transport passengers anywhere they could desire in the city.

Upscale High-Rise Apt · Rooftop Pool + Views

Stay in this brand-new 2025 apartment with luxury amenities. Perfect for work or leisure, it offers everything you need for a comfortable stay. Building Amenities: - 24/7 concierge & secure entry - Rooftop pool & gym with skyline views - Rooftop lounge with a fireplace - Steps from grocery stores & restaurants - Paid parking nearby Unit Highlights: - Stunning views of the city - Work from home space - In-unit washer & dryer - Fully equipped kitchen - Fast WiFi - Modernly designed interior

Studio with View of Skyline in Heart of Pilsen

Explore Pilsen and the beautiful City of Chicago in this unique Loft Style Studio apartment with a view of the Willis Tower and in the Heart of Pilsen. Apartment features a Roku TV with Wifi, private entrance, open layout, closet, bathtub with handheld shower head. 1 queen bed and a sofa bed couch, no kitchen but does have a fridge. Unit is on the 4th floor, no elevator. No Private Parking, just street parking only . Located near major transportation, Divvy Bike Station across the street.

The Oasis / Free street parking

Comfortable home in quiet, walkable, family-friendly neighborhood with quick access to downtown! Recently rehabbed 1st floor unit. Plentiful free street parking, well-stocked kitchen, lush backyard. Walk to parks, coffee shops, grocery store, restaurants, White Sox. Access to red & orange line trains to downtown and tourist attractions. Quick drive to Midway Airport & McCormick Center. No dishwasher Free washer dryer No chores at checkout =) Free early check in/late checkout *if available*

Fully Furnished Apartment Wicker Park Free Parking

Hello and welcome to all seeking a comfortable and convenient place to stay in Chicago! Please enjoy your time away from home in our fully furnished apartment located in the trendy neighborhood of Wicker Park! Please view the list below of all the wonderful amenities we offer to every guest staying out apartment. Again if you have any questions or comments please do not hesitate to ask. I look forward to seeing you and having your apartment ready soon! Thank you! One night available

South Loop 3BD 3BA Condo with Balcony and Parking

Stay in the heart of Chicago’s South Loop at this spacious 3-bedroom, second-floor apartment on Michigan Avenue. Enjoy easy access to Grant Park, Museum Campus, Soldier Field, McCormick Place, and the Lakefront Trail, with CTA trains and buses just steps away. This modern, walkable home features updated bathrooms and kitchen with new fixtures, hardwood floors throughout, a nice front deck, and an in-unit full-sized washer and dryer—perfect for families, groups, or business travelers.

Kasa | Explore the Neighborhood-Mag Mile | Chicago

When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chicago easy. Located just north of downtown Chicago, you'll be steps from Oak Street Beach, a short walk to Michigan Avenue and Millennium Park. With fantastic amenities, our apartments are ideal for extended stays or long vacations. Our tech-enabled apartments offer self check-in at 4pm, 24/7 guest support by text or phone, and a Virtual Front Desk accessed via mobile device.

West Loop Urban Chic Coach House

Welcome to this historic neighborhood in Chicago, a cultural tapestry, rich in history and bursting with energy. Enjoy strolling along the streets lined with historic buildings, savor diverse culinary delights. Bronzeville is not just a place to stay; it is a community experience Enjoy, this one-bedroom, full bathroom historic coach house with a full kitchen, smart TV, and dedicated living space. Unwind in comfort with an in-unit washer/dryer. Plenty of street parking available.

Teeny Tiny Bohemian Lodge - Clean & Affordable

Explore the wonderful neighborhood of Pilsen from this unique little space. Private entrance to your bedroom with an attached bathroom with shower. The entire space is for your private use- nothing is shared. NOTE the bedroom & bathroom ARE the entire space. Designed for one person as a sleeping room. We can not host 2 people. Twin size American bed is 38 x 75 inches. Please CLICK "show more " below BEFORE YOU BOOK/INQUIRE I need you to read and respond to our house rules.

Downtown Penthouse - Mich Ave 2bd | +gym & VIEWS

Feel at Home, Unwind, and Enjoy the amenities you deserve right next to Grant Park! Guests love staying with us because: -Central Location near public transit (no car needed!) -FAST WIFI -En-suite Laundry -Lake & Park are outside our front door -Comfy Queen beds -1 Closed & 1 Loft style bedroom -Shared Rooftop Deck with stunning views -Gym -3 blocks from Red "L" subway -Close to Grant Park, The Bean, Soldier Field, Museums If you're interested in booking, see our FAQs below.

Downtown Chicago Stay with Free In & Out Parking 6

✨ 2 Bedroom / 2 Bathroom Unit ✨ Enjoy a stylish experience at this centrally located place! 🏙️ Spacious 700 sq. ft. modern 2-bedroom, 2 bathroom unit — perfect for corporate travelers 👔 and families looking for a comfortable and stylish escape in downtown Chicago. 🌆 🚗 Free In/Out Parking 🛏️ 2 Bedroom | 2 Bathroom 🛌 2 Queen Beds & 1 Sleeper Sofa (Sleeps 1) 💤 1 Inflatable Airbed 🧸 Portable Crib (For Mini Travel Companion) 📺 Netflix, Hulu, Disney+, & Prime Included

Long Stay,The Jewels,2bd/2ba,UC 2mi,Pkg,DTWN 15mi

Welcome to ABODE6535: The Jewels Suite. This apartment is named after Chicago's popular grocery store chain and its residents' unique way of saying it. :) This vibrantly curated apartment is designed for comfortable extended stays that may make you consider making Chicago home, or at least make sure you feel at home while you're here. You will be welcomed into a well-appointed space with cozy linens, sparkling clean bathrooms and warm touches at every turn.