Book Longman & Eagle: All six rooms from $1,042 per night ($173 per room per night)

There’s definitely room at this inn for your small group above this usually-lively downtown Chicago tavern. Just a hop and a skip from Logan Square, there’s an upscale bohemian ambience to the place, with local art hanging on the walls and exposed brickwork setting the scene.

The rooms emanate contemporary elegance, with clever design touches that make the most of the space in some of the smaller rooms, such as tucked away desks. The largest has a standalone tub and they all come with curated minibars, tech-friendly amenities, and site-specific artworks. Little extras like a large selection of books and vintage tape decks still make it feel special.

Trip Advisor Ranking: 9 out of 24 B&Bs/inns in Chicago

Booking.com Rating: Not yet ranked

Pros: The location couldn’t be better, with the Metro and Logan Square Park both just a short walk away.

Cons: The smaller rooms, while comfortable, have fairly basic setups, such as just hangers on the wall rather than a full a closet, for example.

COVID-19 status and policies: Rooms are cleaned and sanitized according to CDC and EPA guidelines before guest arrival. This includes entrance doors, handrails and high touch areas within the inn. The hotel has removed all high-touch amenities (magazines, pencils, notepads, tapedecks, etc.) from rooms. Disposable items in rooms are removed following each guest stay. Laundry and linens are cleaned with CDC stated guidelines. Staff will not enter guest rooms once they have checked in.