The Uptown neighborhood and nearby Wrigleyville area are lively, historic, and rich with entertainment—from live music venues like The Riviera Theatre to the iconic Wrigley Field. Whether you’re here for a Cubs game, local jazz, or the lakefront, these hotels offer comfort and convenience.
1. Hotel Zachary, Chicago, a Tribute Portfolio Hotel
Why stay here: Located right across from Wrigley Field—ideal for Cubs fans.
Pros:
- Baseball-themed luxury hotel
- Bars and restaurants on-site
- Views of Wrigley Field
Cons:
- Can be noisy on game days
- Price surge during baseball season
- Limited parking
2. The Guesthouse Hotel
Why stay here: All-suite boutique hotel in Uptown with home-style comfort.
Pros:
- Full kitchens in suites
- Family-friendly
- Walkable to Andersonville and Uptown nightlife
Cons:
- No restaurant on-site
- Pricey for longer stays
- Residential feel may not suit all
3. Majestic Hotel Chicago
Why stay here: Quaint, English-style boutique hotel steps from Lake Michigan and Wrigley Field.
Pros:
- Cozy charm with baseball-themed decor
- Free continental breakfast
- Quiet, residential area
Cons:
- No elevator
- Older rooms
- No gym or restaurant
4. Best Western Plus Hawthorne Terrace Hotel
Why stay here: A solid mid-range option near Lakeview and Wrigley Field.
Pros:
- Great location for nightlife and baseball
- Sauna and fitness room
- Pet-friendly
Cons:
- Limited parking
- Some rooms are small
- Dated decor in some areas
5. City Suites Hotel
Why stay here: A stylish Art Deco-inspired hotel close to the Belmont Red Line.
Pros:
- Funky retro decor
- Free breakfast
- Near music venues and shops
Cons:
- No parking
- No elevator
- Occasional street noise
6. Roscoe Village Guesthouse
Why stay here: Great for longer stays or groups; apartment-style units.
Pros:
- Full kitchens
- Quiet neighborhood
- Close to dining and boutiques
Cons:
- Not a traditional hotel
- Self-check-in only
- No daily housekeeping
7. Chicago Getaway Hostel
Why stay here: Budget-friendly stay for solo travelers or students.
Pros:
- Low rates
- Free breakfast and events
- Near DePaul and Lincoln Park
Cons:
- Shared facilities
- Basic rooms
- Youth-oriented crowd
8. The Wheelhouse Hotel
Why stay here: Urban, baseball-themed boutique hotel one block from Wrigley.
Pros:
- Unique decor
- On-site bar and pizza joint
- Cool rooftop lounge
Cons:
- Loud after Cubs games
- Limited parking
- Some rooms lack views
9. Wrigley Hostel
Why stay here: Social atmosphere right in the heart of Wrigleyville.
Pros:
- Very close to Wrigley Field
- Game nights and pub crawls
- Great value
Cons:
- Shared dorms
- Noisy environment
- Few amenities
10. House 5863 Bed & Breakfast
Why stay here: Hidden LGBTQ+-friendly B&B in Uptown with stylish rooms.
Pros:
- Modern, clean design
- LGBTQ+ inclusive space
- Near Argyle Red Line
Cons:
- Minimal staff on-site
- Self-service model
- Small property
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