Cheap Chicago Vacations

Chicago

Your Chicago vacation

From food to theater and Lake Michigan to the Loop, Chicago is home to some equally big names. But you don't need to fly in on Obama's Air Force One or have pockets as deep as Oprah to be able to experience a Chicago vacation at its fullest. Take a stroll down the Magnificent Mile, catch a Cubs game at Wrigley Field, and soak up the waterfront culture of the Second City.

Before you rush to Millennium Park, allow CheapTickets to help you with the planning. We'll share the city's top highlights that will blow your mind -- without blowing your budget.

Cheap Vacation Packages

Cheap Chicago Vacation Packages

The Talbott Hotel

4 stars
4.6 / 5 826 reviews
The Talbott Hotel in the heart of the Gold Coast offers spacious rooms with complimentary amenities including wireless internet and access to Equinox Fitness. Located steps from Chicago's Magnificent Mile and Rush Street, the heart of Chicago's night life. Voted as an Orbitz Best of the Best hotel. The Talbott Hotel is recognized as a leader in both leisure and business travel. It offers impeccable service with its concierge staff, all Les Clefs d'Or members, to assist with your evening plans or sightseeing. After a day of excitement, relax and unwind in your oversized guest room. The elegant marble bath stocked with fine Molton Brown Bath and Spa products in your guest room or your suite. Dry off with your luxurious Frette bath linens, and sink into a terrycloth robe while enjoying a program on your 42" LCD flat screen television with 30 High Definition Channels. Nightly turndown service; we will refresh your room, turn down your bed and leave you with delectable chocolate. You will be fully rested and ready to start another day of exploration after sleeping in one of our plush pillow top beds with luxurious linens, down pillows and comforter. Another day of relaxation and luxury awaits you tomorrow Imagine the rest. * Certified "Green Seal" Hotel. * 100% of the hotels electrical carbon footprint is offset by Wind Energy. * Four Diamond Rated by AAA. * Guests must be at least 21 years of age to check in. A $20 fee per person, per night will apply to all reservations where there are more than 2 people staying in a room and will be charged directly by the hotel. Extra beds are also available upon request for a fee of $24/night. See Front Desk for more information.
Value Save 25% on 7 nights or more
Flight + Hotel
Book a package for more savings!
Select
Hotel only
Nightly rates from $165

The Whitehall Hotel

4 stars
3.8 / 5 1094 reviews
Gold Coast boutique meets 1920s charm The Whitehall Hotel manages that rare combination of location and ambiance. The hotel is situated one block from the Magnificent Mile and Rush Street nightlife district, but tucked away from the tourist fray on a residential street. One of Chicago's oldest luxury hotels but certainly no slouch, the Whitehall brims with 19th century elegance -- imagine chandeliers, wood paneling and tufted leather chairs, all restored to match the original European grace and grandeur of this Gold Coast gem. HighlightsOne block from the Magnificent Mile and Rush Street nightlifeWalk to John Hancock Center, Water Tower Place, Lake Michigan and Oak Street BeachDining at Fornetto Mei, a Pan-Italian restaurant Fitness center Rooms Chicago's independent boutique Whitehall Hotel, which has hosted guest celebrities like Katharine Hepburn, Richard Burton, Sophia Loren, Paul Newman, The Beatles and Mick Jagger over the years, provides intimate guest rooms and suites decorated with antique mahogany tables and nightstands, wood headboards, down duvets and marble bathrooms. High-speed Internet and wireless access are available in rooms (fees apply). FeaturesGuests at The Whitehall Hotel won't have to worry about leaving their dog or cat at home. The hotel welcomes pets less than 20 pounds for a non-refundable deposit. For an upscale casual dining option, dine at Fornetto Mei, which traverses Asia and Italy with its menu of oven-fired, thin crust pizza and house-made pot stickers or sample dumplings at Mei's Corner. A cozy atrium bar welcomes guests and invites sampling of the restaurant's 200 plus global and California boutique wines. Transportation O'Hare International Airport (15.3 mi/24.7 km)Chicago Midway Airport (9.7 mi/15.7 km)Blue Line (Washington/Dearborn) (1.1 mi/1.8 km)Orange Line (State/Lake) (0.9 mi/1.5 km)McCormick Place Convention Center (3.3 mi/5.3 km) AttractionsThe Magnificent Mile (0.1 mi/0.1 km)The Gold Coast (0.1 mi/0.2 km)Oak Street Beach (0.3 mi/0.4 km)Rush Street (1 block)Navy Pier (0.8 mi/1.3 km) Business Event space for six to 100 guestsBusiness center with computersHigh-speed Internet access (fees apply) Policies and feesGuests must be at least 21 years old to check in.Parking fee is $49.The Whitehall Hotel is a 100% smoke free property.
Flight + Hotel
Book a package for more savings!
Select
Hotel only
Nightly rates from $98

Inn of Chicago, an Ascend Collection hotel

3 stars
3.4 / 5 151 reviews
Contemporary style, European charm in ChicagoIn the Roaring '20s, this boutique Streeterville hotel hosted celebrities and showgirls. While those times have faded, the air of glamour remains at the Inn of Chicago, an Ascend Collection hotel. For proof, just stroll the lobby, where zebra ottomans, fresh-cut orchids and metallic embossed walls create drama and urban appeal. With its central location and focus on value, the Inn of Chicago is a gem for business or leisure travelers seeking convenient access to the Magnificent Mile and its many diversions. Highlights Prime Chicago location just east of Magnificent MileFree high-speed wireless Internet accessComplimentary stay for children under 18The 22nd floor Skyline Terrace RoomsThe rooms and suites at the Inn of Chicago feel more like apartments than hotel rooms, and that’s on purpose. Back in the 1920s, the former Hotel St. Clair offered one-bedroom apartments, and the effects linger today at the Inn of Chicago. Space for entertaining, working and lounging are separate from the sleeping area. Big picture windows with skyline views, photos of Chicago, zebra upholstery and unique layouts lend to a chic city vibe. FeaturesGreat city views might well be the most valuable cache for Chicago hotels and for the Inn of Chicago, this view comes at the Skyline Terrace on the 22nd floor. The Sky Suites also provide lofty views, while a dedicated party space accommodates up to 100 guests for weddings and other social events. Transportation O’Hare International Airport (15.6 mi/25.1 km) Midway Airport (9.8 mi/15.9 km) Blue Line (Grand) (1.7mi/2.7 km) Orange Line (State/Lake) (0.5 mi/0.9 km) McCormick Place Convention Center (2.9 mi/4.6 km) Attractions The Magnificent Mile (0.1 mi/0.1 km) Water Tower Place (0.4 mi/0.6 km) Navy Pier (1 mi/1.6 km) Lake Michigan (0.2 mi/0.3 km) Millennium Park (0.7 mi/1.1 km) Business Business center work station 5 meeting rooms 5,500 square feet of function space for up to 125 guests Complimentary wireless Internet access Concierge services
Flight + Hotel
Book a package for more savings!
Select
Hotel only
Nightly rates from $73

Congress Plaza Hotel at Grant Park

3 stars
3.3 / 5 827 reviews
Historic hotel on Michigan Avenue by Grant ParkGuests at the Congress Plaza Hotel at Grant Park hotel enjoy value prices and a convenient location across from Grant Park, Buckingham Fountain, Millennium Park, the Art Institute and Lake Michigan. Designed to accommodate large groups, the 850-room hotel has hosted legions of tourists, conventioneers and even the nation’s presidents since the World’s Columbian Exposition in 1893. Its presence among Chicago architecture is unmistakable: Just look for the oversized sign in all red caps. Highlights Spectacular views of Grant Park, Buckingham Fountain, Lake MichiganTwo restaurants and a lounge on site Wireless Internet in the lobby RoomsRooms at the Congress Plaza Hotel at Grant Park hotel favor space over flash. Find rooms and spacious suites of various sizes -- many with lakefront views -- as well as high ceilings and parlor seating. Wired and wireless Internet access are available for a fee. FeaturesThe Congress Plaza Hotel at Grant Park serves as a top reception site for weddings, conferences and other formal events. The lobby with its massive mosaic-tiled ceiling inspires awe in both guests and architecture fans. More than 50,000 square feet of meeting space, including the gorgeous Gold Room with its gold-leaf covered walls and ceilings, lend opulence to any occasion.Diners visit the Gazebo Restaurant, a casual restaurant serving breakfast and lunch, or Rafael's Steakhouse, a more intimate dinner venue. Cocktails and pub fare are available in the lounge.Other property amenities include a barbershop, game room and fitness center. Transportation O’Hare International Airport (16.1 mi/25.8 km) Midway Airport (8.9 mi/14.4 km) Blue Line (LaSalle) (0.9 mi/1.5 km) Orange Line (Library) (0.3 mi/0.5 km) McCormick Place Convention Center (1.7 mi/2.7 km) Nearby attractions Grant Park (across the street) State Street (0.1 mi/0.2 km)Buckingham Fountain (0.3 mi/0.5 km)The Art Institute of Chicago (0.4 mi/0.6 km)Millennium Park (0.5 mi/0.9 km)Soldier Field (1 mi/1.6 km)The Magnificent Mile (1.3 mi/2.1 km) Policies and feesValet Parking $39.00 for overnight parkingSelf-Parking $35.00 for overnight parkingIn-room wired/wireless Internet access is charged at $9.95 + tax for 24 hours.
Value Save 10% on your stay
Flight + Hotel
Book a package for more savings!
Select
Hotel only
Nightly rates from $125

Hotel Felix

4 stars
3.9 / 5 60 reviews
A green hotel in the Windy CityA hotel that offers luxury yet cares for the environment? That's Hotel Felix. Located downtown, the Hotel Felix Chicago offers guests a variety of excellently priced rooms and amenities with an eco-friendly approach. The Hotel Felix Chicago greets guests with a surprisingly modern design, blending a mix of earthy tones and post-modern decor. Guests enjoy a variety of facilities including business rooms, a fitness center, a comprehensive spa and 24-hour concierge service. 3 Reasons To Stay Eco-friendly hotel, the first in Chicago to be Gold LEED certifiedLocated in downtown Chicago, in close proximity to all of the area landmarksFrench Bistro-style dining serving European cuisines at LM Bistro on site Hotel Felix Chicago RoomsThe Hotel Felix Chicago derives its name from the Latin word for "happy," and guest rooms here encourage the feeling. Beds boast luxurious linen and pillows, ensuring that guests can relax and enjoy their surroundings. Each room boasts tasteful decor with muted tones and chocolates that give guests a feeling of elegance. Rooms at the Hotel Felix Chicago are spacious and illuminated with great swathes of natural light due to their large windows. These windows enable guests to enjoy sweeping vistas of the Chicago skyline that are breathtaking day or night. No hotel room would be complete without amenities, and the Hotel Felix Chicago offers plenty of them. Each room features a high-speed Wi-Fi connection, a flat-screen HD television, a safety deposit box, and room service on demand. Bathrooms have a clean and minimalist feel with pleasant, bright lighting and full amenities including a complimentary robe. Each room is very environmentally conscious. Lighting is fully energy efficient and guest rooms feature carpets made from recycled materials. Things To DoMuseum of Contemporary Art (0.8 mi/1.3 km)Chicago Harbor (1.8 mi/2.9 km)University of Illinois (2.4 mi/3.4 km)Grant Park (2.6 mi/4.2 km)O'Hare International Airport (17.5 mi/28 km)
Flight + Hotel
Book a package for more savings!
Select
Hotel only
Nightly rates from $90
See more Hotels in Chicago
Back to menu Return to top
Cheap Flights
Departure Arrival Travel dates Round-trip
New York Chicago Tue, Aug 13 - Wed, Sep 4 $171
Los Angeles Chicago Thu, Aug 15 - Mon, Aug 26 $304
Washington DC Chicago Thu, Aug 15 - Tue, Aug 20 $204
San Francisco Chicago Sat, Aug 17 - Mon, Aug 26 $361
Newark Chicago Tue, Jul 30 - Tue, Aug 6 $270
Atlanta Chicago Sat, Jun 22 - Tue, Jun 25 $221
Seattle Chicago Wed, Aug 7 - Wed, Sep 4 $356
Boston Chicago Wed, Aug 14 - Mon, Aug 26 $229
Dallas Chicago Tue, Aug 13 - Tue, Sep 10 $184
Denver Chicago Tue, Jul 30 - Tue, Aug 20 $138
Phoenix Chicago Wed, Aug 14 - Wed, Aug 21 $264
Orlando Chicago Wed, Aug 14 - Tue, Aug 20 $247
San Juan Chicago Thu, Aug 15 - Mon, Aug 26 $391
Mexico City Chicago Mon, Aug 5 - Sat, Aug 17 $356
Philadelphia Chicago Tue, Aug 6 - Fri, Aug 9 $308
San Diego Chicago Tue, Aug 6 - Tue, Aug 13 $288
Fort Lauderdale Chicago Wed, Aug 7 - Wed, Aug 21 $211
Las Vegas Chicago Tue, Jul 23 - Tue, Jul 30 $288
Guadalajara Chicago Tue, Aug 13 - Wed, Sep 4 $471
Tampa Chicago Wed, Jul 31 - Tue, Aug 6 $238
Houston Chicago Thu, Aug 15 - Wed, Aug 21 $215
Baltimore Chicago Tue, Jul 30 - Thu, Aug 15 $271
Honolulu Chicago Thu, Aug 15 - Mon, Aug 26 $861
Orange County Chicago Wed, Aug 14 - Wed, Aug 21 $320
See more flights to Chicago
Back to menu Return to top

Best time to take a vacation to Chicago

  • If you visit Chicago in the early fall you will experience the best of its weather as it retains its warm temperatures but loses the humidity of the summer months. Spring time is cooler, and it is a good time to capture those cheaper flights and hotels. The Chicago Blues Festival every June attracts headline acts from around the country and is extremely popular, as is the early three-day snow sculpturing exhibition held every winter on Navy Pier. Grant Park at the harbor hosts an annual Taste of Chicago Food Festival which, as you might expect, appeals to a wide audience.

Insider tips for Chicago travel

  • Pancho Pistolas

    Dine out at Pancho Pistolas restaurant serving delicious Mexican cuisine in the Bridgeport neighborhood.

  • Ping Tom Memorial Park

    Admire the Oriental architecture on a steady stroll through the pleasant and quiet surroundings of Ping Tom Memorial Park.

  • Montrose Harbor

    Walk the lake-front trail north towards Montrose Harbor with some incredible views of the city skyline.

  • Alta Vista Terrace

    Capture the history of Alta Vista Terrace close to Wrigley Field, modeled on a block of row houses in London.

  • Cafe Selmarie

    Take lunch at the charming Cafe Selmarie overlooking the Lincoln Square Fountain and consume some mouth-watering cakes.

Chicago highlights

  • Chicago highlights

  • Navy Pier

    For a bustling carnival vibe along Lake Michigan, wander along the Navy Pier promenade and catch the spirit of Chicago. Bring the kids to the Children's Museum, Shakespeare Theatre or Stained Glass Gallery, and marvel at the incredible skyline views from the 150-foot Ferris wheel. Grab a bite to eat at Chicago institution Harry Caray's, and rest your weary feet to enjoy the free weekly fireworks.

  • Magnificent Mile

    The Mag Mile is a revered for its incredible shopping and eating scene, as well as the festivities that occur throughout the year. Lined by colorful tulips in the springtime and glittering lights during the holidays, the Mag Mile is chockablock with department stores and notable landmarks, from the Wrigley Building to Oak Street Beach. For incredible views on your Chicago travels, head to the Hancock Observatory or spend a few bucks on a cocktail in the Signature Lounge.

  • Lincoln Park Zoo

    For an easy escape without having to spend a cent on your Chicago travels, take the afternoon to meander through the menagerie at the Lincoln Park Zoo. Not only is it brimming with wildlife exhibits and beautiful historical architecture, it's totally free and open 365 days a year.

  • Cultural Chicago

    If you want to experience the cultural side of the Second City on your Chicago vacation, make a beeline for the Chicago Cultural Center where admission is free. After taking in the impressive architecture and stunning Tiffany dome, head to the Art Institute across the street to view the amazing collection of Impressionist art and the new Modern Wing. Take a stroll to the Buckingham Fountain and laze in the sun, or take in a nighttime light show.

  • Millennium Park

    Chicago has plenty of parks, but this one is worth a special mention. An impressive feat of engineering, landscaping and cultural celebration, Millennium Park is home to the iconic Cloud Gate sculpture and splashy Crown Fountain video sculpture. Enjoy a concert at Jay Pritzker Pavilion, the go-to spot for the best in outdoor entertainment.

See Chicago travel-guide Site Map
Flight only Hotel only Car only Activities Cruises
Flight + Hotel Flight + Car Hotel + Car Flight + Hotel + Car
Search by city, point of interest, region, or airport Search by address
Room 1
Ages of children at time of trip (for pricing, discounts)
Additional options