9 Hipster-Chic Hotels in Chicago Under $250/Night

See recent posts by Jane Reynolds

Chicago always makes the top 10 list of the most visited U.S. destinations, and its particularly “hot” in the summertime – probably because it’s not so, well, hot. While the Windy City’s winters are infamously brutal, summers here are mild and sunny. In fact, statistics show that Chicago was the second most popular U.S. city destination among travelers last summer; only NYC could best it.

The downside to Chicago’s lovely summer weather, rich culture, and well-established dining and nightlife scene is that the city’s hotel prices can be extremely high. Fortunately, we here at Oyster.com are hotel experts and we’ve found some deals. Below you’ll find nine hipster-chic Chicago hotels for under $250/night – some are as low as $55/night. And we promise, you’ll actually want to book this cool spots. 

Rates are based on June dates.

1. MileNorth, a Chicago Hotel

Located half a block from the famed Magnificent Mile, luxury boutique hotel MileNorth strives to give guests a modern, home-away-from-home experience that contrasts with the ornate, Gilded-Age sensibility of many other area hotels. With a cozy, living-room-style lobby whose cafe serves Starbucks, as well as a rooftop lounge with sweeping views of the city, the MileNorth can be both relaxed and trendy at the same time. The rooms are spacious for the neighborhood and price (which hovers around $200/night), with a unique bi-level configuration and all the requisite modern amenities, including flat-screen TVs, iPod docks, mini-fridges, and coffeemakers. 

2. Holiday Jones

Holiday Jones is technically a hostel, but don’t let that deter you; this hip millennial spot has the vibe of New York’s Ace Hotel, but rates that are significantly lower. While most rooms are under $100/night, you can score some for as low as $65/night. Sure, many have bunk beds and there’s no gym or pool, but great perks include free breakfast and expansive common areas with guest computers, a pool table, billiards, and a communal kitchen.

3. The James Chicago

The James is one of Chicago’s top luxury hotels, and is located in River North, a block from the Magnificent Mile. This generally means rates soar over $400/night, but we found some nights in June when you can book a room for just under $250. The public spaces here are modern and sometimes quirky, while the 297 rooms are crisp and clean. They’re minimally decorated without being stark, and some have clever design to maximize space, as well as big flat-screen TVs, impressively stocked minibars, and comfortable beds

4. Ivy Boutique Hotel

The 60-room Ivy Boutique Hotel is a well-positioned, upscale property, right off of Michigan Avenue. Rooms have beautiful, modern decor along with automatic window curtains and marble bathrooms with rainfall showers. There is a seasonal, lovelyrooftop terrace and cocktail lounge offering great city views, plus a lobby bar that serves breakfast. Guests can book studios for $150/night this summer, or spend just about $25 more for a suite. However, thanks to the hotel’s prime location and reasonable rates, rooms book up very quickly.

5. Hyatt Chicago Magnificent Mile

Everything in this modern, upscale hotel was upgraded in 2015, and it shows everywhere, except perhaps in the prices, which can occasionally dip as low as just about $250/night. Rooms at this Hyatt Chicago are spacious, comfortable, and stylishly furnished with amenities worthy of a four-pearl property. Tastefully decorated accommodations have modern touches like iPod/iPhone docking stations and plug-in media centers. Located in the heart of downtown, it’s a good choice for both business and leisure travelers. 

6. Chicago Getaway Hostel

With rates as low as $55/night, the Getaway Hostel is certainly the least expensive property on this list – but we’d argue that its sleek design and overall hip vibe make it worthy of consideration for your next Chicago trip. Located in Lincoln Park, the property offers a mix of private, shared, and dorm-style rooms, as well as amenities such as free housekeeping (upon request), a 24-hour guest kitchen, a game room, and bike rentals.

7. W Chicago – Lakeshore

The 520-room W Chicago – Lakeshore delivers the chic decor you’d expect from a W, and its impressive features — a spacious gym, attractive indoor pool, on-site Bliss Spa, and absolutely stunning views of Lake Michigan and Navy Pier — make this a solid upscale option. Current Restaurant and the Living Room lobby bar draw guests and locals, as does the rooftop terrace. Nightly rates here are usually over $300, but Sundays usually are less expensive, with rates around $230/night.

8. Tremont Chicago Hotel at Magnificent Mile

The mid-range Tremont Chicago Hotel at Magnificent Mile is a charming boutique hotel located right by its namesake bustling avenue lined with shops and restaurants. Its 135 rooms are stylish and elegant thanks to a recent renovation and have flat-screen TVs, coffee/tea makers, and free bottled water; rates hover just over $200/night. Though there aren’t many features on-site, the hotel’s lobby connects to the next-door Mike Ditka’s Restaurant, which offers a breakfast buffet (for a fee) as well as meeting spaces. 

9. Hotel Palomar Chicago

The 261-room Hotel Palomar is one of the best Kimpton hotels in the city, and the only one in River North, near the Magnificent Mile. Its lovely indoor pool with a sundeck and its free nightly wine hour are both highlights, and the big, stylish rooms are equipped with iPod docks, 37-inch flat-screen TVs, and Etro bath toiletries. All in all, it’s a great pick for the price; rates are generally between $200 and $250/night, but some nights this month dip below $150.

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