The 7 best cheap but cool hotels in Chicago right now

💎 Best for: a ‘live like a local’ vibe

Spanning two adjoined historic buildings—the 1929 Art Deco Northwest Tower and a 1905 industrial warehouse—The Robey packs immense personality into a quirky building. Its 89 Tower rooms blend a mid-century boutique style with warm, casual service. Meanwhile, the warehouse's Annex Lofts embrace an industrial vibe with high ceilings and concrete floors.

While the minimal decor feels a bit spare, it’s undoubtedly cool. Corner king rooms feature wedge-shaped layouts with stunning two-wall skyline views. Guests enjoy all-day brunch at Cafe Robey, tiki cocktails at Clever Coyote, and rooftop drinks at The Up Room. The property also features a unique, triangular heated rooftop pool deck with panoramic views, plus a partnership with a nearby athletic club for gym access. It is an ideal, romantic launchpad for an urban rendezvous.

Time Out tip: Hotel guests get exclusive early access to The Up Room at from 4.30pm (before it opens to the public at 5pm). Get your skyline snaps during this window! 

Address: 2018 W. North Avenue, Chicago
Price: Starting around $195, with many dates in the $250-$550 range depending on the season
Closest transport: 0.5-block walk to CTA Blue Line with service to O’Hare Airport (30 minutes) and Chicago’s downtown district (20 minutes).

🧖‍♀️ Discover our favorite spa hotels in Chicago right now

 💎 Best for: dinner and a show

Steeped in Old Hollywood glamour, The Allegro Royal Sonesta Hotel features a grand lobby with a double staircase, velvet settees, and Art Deco starburst lighting. This dramatic aesthetic carries into its 483 rooms, which feature metallic wallpaper, gold satin shams, and miniature stage-curtain draperies. Select two-room corner king suites upgrade the experience with spacious sitting areas and large jetted tubs.

On the second floor, Legato Lounge serves upscale cocktails and a concise menu featuring standard American classics like ribeye steak, pan-seared branzino, and mushroom bolognese. Located directly in the heart of the Loop’s Theater District, the hotel shares a block with the Cadillac Palace Theatre, putting major Broadway stages within easy walking distance. 

Time Out tip: Be aware that some of the food markets around here aren’t open on weekends. 

Address: 171 W. Randolph St., 60601, Chicago 
Price per night: Starting at $199
Closest transport: 1-block walk to Madison Street Loop Link bus station; 2-block walk to CTA Blue, Brown, Green, Pink, Orange and Purple Line trains (Clark/Lake station); 30-minute taxi ride to O’Hare Airport and Midway Airport. 

💝 Read about Chicago’s most romantic hotels in our complete list

💎 Best for: a touch of whimsy 

Built back in 1927, the classic Georgian Revival exterior of The Talbott Hotel gives way to a whimsically sophisticated interior in Chicago’s swanky Gold Coast. Offering a boutique, intimate alternative to massive luxury high-rises, its 178 guest rooms feature romantic touches like brass-trimmed floral headboards, velvet accent chairs, and a soothing ivory palette.

Clever nods to hotel history—like rotary elevator phones and vintage-inspired bluetooth speakers—sit alongside modern conveniences like hallway filtered water stations. On-site Mediterranean café Laurel serves standout dishes like braised lamb shank shawarma and decadent mushroom toast. The property features a 24/7 fitness center and a mandatory destination fee packed with perks like museum tickets and drink credits. 

Time Out tip: Walk over to the historic Fourth Presbyterian Church on Michigan Avenue for a free concert on Fridays. 

Address: 20 E. Delaware Place, 60611, Chicago
Price: Starting at about $140 and up, with many dates in the $225-$350 range depending on season. 
Closest transport: Half a block walk to State Street buses; 1-block walk to Michigan Avenue buses; 3-block walk to CTA Red Line (Chicago station); 40-minute taxi ride to O’Hare and Midway airports. 

👑 Here’s our collection of the absolute best hotels in Chicago right now

Housed in a charming historic Lakeview building, this boutique hotel is simple yet elegant. The lobby’s funky animal portraits and cowhide chairs make a bold impression, but it’s the prime location that seals the deal. Just steps from Lincoln Park, guests have easy access to the Lincoln Park Zoo, miles of footpaths, and countless quaint picnic spots (and the Lakefront Trail is also nearby). The surrounding blocks are flanked by bars, restaurants, and local shops, so be sure to try some out during your stay. 

Time Out tip: If you want to venture out of the neighborhood, the Diversey Brown Line station is less than a half-mile away by foot.

Address: 555 W Surf St, Chicago, IL 60657
Price per night: From $130 per night
Closest transport: Diversey Station (CTA Brown and Purple Lines)—a 10-minute walk southwest.

Hotel Chicago West Loop’s central location on the Near West Side takes you off the typical tourist path. Take a short bus ride to Little Italy or Pilsen, the historic heart of Chicago’s Hispanic community; watch the Chicago Bulls or Chicago Blackhawks at the nearby United Center; or head to a festival or concert in Union Park. The hotel’s amenities include a fitness center and complimentary coffee—though nearby cafes like Froth may tempt you to skip the free java. The varying accommodations—king, queen, full and bunk bed options are available—are simple and decorated with colorful Chicago-themed art.

Time Out tip: Book a mural room. 

Address: 1622 W Jackson Blvd, Chicago, IL 60612
Price per night: From $150
Closest transport: Illinois Medical District Station (CTA Blue Line)—roughly a 6-minute walk (0.3 miles) south. Ashland Station (CTA Green and Pink Lines) is also about a 10-minute walk north.

This small, family-owned and run guesthouse is nestled in Bronzeville, the city’s historic African American neighborhood and former home of notable residents like Gwendolyn Brooks, Louis Armstrong and Ida B. Wells. The owners of Villa DuBois Guesthouse set out to design a hotel that truly feels like home, outfitting the property with rooms that are cozy-yet-tasteful and boast lots of natural light. Guests enjoy dedicated parking spaces and access to communal outdoors spaces. Plus, you’re just a ride on the Green Line away from the Loop, McCormick Place and the Lakefront.

Time Out tip: Note that lower tier rooms have a shared bathroom set up.

Address: 3722 S Calumet Ave, Chicago, IL 6065
Price per night: $90–$140
Closest transport: 35th-Bronzeville-IIT Station (CTA Green Line)—about a 4-block walk northwest.

For the best gateway to exploring one of Chicago’s most vibrant South Side neighborhoods–home of the Museum of Science and Industry and the University of Chicago–while enjoying stunning lakefront views, you can’t beat this Hyde Park hotel. The Chicago Lake Shore Hotel features a large outdoor pool and basic-yet-comfortable rooms. Hop on the nearby Lakefront Trail to walk, cycle and run, or head to 49th Street Beach or admire the skyline views at Promontory Point. 

Time Out tip: You’re minutes from the neighborhood’s stretch of bars and restaurants, like acclaimed Southern fare at Erick Williams’s recipient of a Michelin Bib Gourmand, Virtue, or hip music venue The Promontory. 

Address: 4900 S DuSable Lake Shore Dr, Chicago, IL 6061
Price per night: From $100
Closest transport: 47th St. (Kenwood) Station (Metra Electric District Line)—roughly a 12-minute walk west. (The CTA Red/Green line train stations are further west, but the hotel has historically offered local shuttle connections).