4 nights - split hotel stays?

Question

I'll be traveling solo to Chicago for the first time for 4 nights, December 7-11. It's sort of a spontaneous trip, and all I really know is that I'd like to visit the Art Institute, the Christmas Market, eat some great food, visit some bars (both local dives and fancier cocktails), and just generally take in the sites. I have both Hilton and Marriott points from work travel, so my question is this: would it be worth splitting up my stay at two different hotels? And if so, which two areas would be recommended? Would it make sense to stay 2 nights near the Mag Mile and then 2 nights in a less touristy spot to experience more of a local vibe? I like long walks but also have no issue taking public transit just about anywhere. Thanks all!

Answer

That sounds like a great trip to Chicago! Splitting your stay between two hotels could be a fun way to experience different parts of the city and get a feel for both the touristy spots and more local areas. Here are some things to consider when deciding whether to split your stay:

Benefits of splitting your stay:

It allows you to explore two different neighborhoods, which can give you a broader experience of the city.
You can stay closer to certain attractions at different points of the trip (e.g., near the Magnificent Mile for shopping and sights, then in a more local neighborhood to see how Chicagoans live).
If you’re into walking, Chicago has many walkable neighborhoods, so being near one area for a couple of days allows you to dive deeper into the vibe of the neighborhood.

Hotel Locations to Consider:

1. Near the Magnificent Mile (Mag Mile) - First 2 Nights
The Magnificent Mile is Chicago’s central shopping and tourist district. It’s home to many iconic spots like the Art Institute, the Christmas Market at Daley Plaza, and plenty of restaurants, bars, and shops. You’ll be in the heart of the action, which is great for a first-time visitor. Plus, public transit is easily accessible from here. Hilton and Marriott both have great options in this area, so you’ll be close to the shopping, landmarks, and some upscale bars and restaurants. This area is busy and vibrant, and perfect if you want to take in Chicago’s best-known attractions.

Check out the Art Institute (just a short walk), the Christmas Market, and nearby iconic architecture like the John Hancock Center and Water Tower.
For bars, check out the Signature Lounge in the Hancock Tower for a fancy cocktail and stunning views, or visit The Violet Hour in Wicker Park for a speakeasy-style experience.
Great food options nearby include Joe’s Seafood, RPM Steak, and local spots like Au Cheval for a famous burger.

2. More Local Neighborhood - Last 2 Nights
For a more authentic, local vibe, you could switch to one of Chicago’s great neighborhoods. Here are a few options that would give you a different feel from the bustling tourist areas:

Wicker Park/Bucktown: This area is known for its artsy vibe, trendy boutiques, coffee shops, and great local bars. It’s an area where young locals go to hang out, and it has a more bohemian, laid-back vibe compared to the Magnificent Mile. It’s also home to some excellent restaurants like The Violet Hour (a hidden cocktail bar), Big Star (for tacos), and Piece Brewery (for great pizza and beer). It’s also just a short ride on the Blue Line to downtown if you want to easily access the more touristy spots.
Logan Square: Another cool neighborhood with a local feel, Logan Square is known for its craft cocktail bars, local eateries, and street art. You’ll find hip spots like Whistler for cocktails, and Longman & Eagle for a classic Chicago dining experience. It’s a little off the beaten path but has a lot to offer.
River North: If you like to stay close to downtown but want something a little less hectic than the Mag Mile, River North is an excellent option. It’s a great area for foodies, with tons of restaurants and bars, including Girl & The Goat and The Aviary (a high-end cocktail bar). Plus, you’re still close to the Magnificent Mile, so you can easily take a quick walk to the main attractions.

Things to Consider:

If you’re only in town for four nights, keep in mind that Chicago is a large city, so you may spend a little more time commuting if you stay in a neighborhood further from the tourist attractions. However, public transit in Chicago is excellent, and taxis/ride shares are always available.
Also, if you’re traveling solo, you may feel more comfortable staying in a more touristy area for the first half of your trip, then move to a quieter, local area for a more relaxed vibe.
Lastly, during December, expect colder weather, so indoor activities like museums, shopping, and dining will be a great way to spend your days!

Overall, splitting your stay between two hotels is a great idea for a diverse experience of Chicago. If you want to stay in the middle of the action at first and then explore the local vibe later, the combination of staying near the Mag Mile and then moving to a more local neighborhood like Wicker Park or River North will give you the best of both worlds.