 | $31* | Chicago | Get the cheapest Compact Car rental in Chicago, IL, starting from as low as $30. travelgrove |
 | $182* | Chicago | $178: 4-star Chicago hotel + Complimentary Room Upgrade ($30 Value), May 28 to May 31 bookingwiz.com |
 | $800* | Chicago | To Chicago $782 from New Orleans: flight + 2 nights hotel (MSY-ORD) bookingwiz.com |
 | $31* | Chicago | Get the cheapest Full-Size Car rental in Chicago, IL, starting from as low as $30. travelgrove |
 | $697* | Chicago | To Chicago $682 from Jacksonville: flight + 2 nights hotel (JAX-ORD) bookingwiz.com |
 | $1041* | Chicago | To Chicago $1018 from San Jose: flight + 2 nights hotel (SJC-ORD) bookingwiz.com |
 | $28* | Chicago | Get the cheapest Standard Car rental in Chicago, IL, starting from as low as $27. travelgrove |
 | $652* | Chicago | To Chicago $638 from San Antonio: flight + 2 nights hotel (SAT-ORD) bookingwiz.com |
 | $63* | Chicago | $61* - $61.00 & up 4-star hotels in Chicago bookingwiz.com |
 | $542* | Chicago | To Chicago $530 from Minneapolis: flight + 2 nights hotel (MSP-ORD) bookingwiz.com |
 | $665* | Chicago | To Chicago $650 from Pittsburgh: flight + 2 nights hotel (PIT-ORD) bookingwiz.com |
 | $661* | Chicago | To Chicago $646 from Charlotte: flight + 2 nights hotel (CLT-ORD) bookingwiz.com |
 | $665* | Chicago | To Chicago $650 from Kansas City: flight + 2 nights hotel (MCI-ORD) bookingwiz.com |
 | $23* | Chicago | Get the cheapest Compact Car rental in Chicago, IL, starting from as low as $22. travelgrove |
 | $31* | Chicago | Best Mid-Size SUV rentals in Chicago, IL starting from as low as $30. travelgrove |
 | 60% OFF | Chicago | $149+* - Luxury 4.5 Star Chicago Loop Mystery $149 - Save 60% bookingwiz.com |
 | $111* | Chicago | $108* - $108.00 & up 4.5-star hotels in Chicago bookingwiz.com |
 | $530* | Chicago | To Chicago $518 from Detroit: flight + 2 nights hotel (DTW-ORD) bookingwiz.com |
 | $21* | Chicago | Get the cheapest Standard Car rental in Chicago, IL, starting from as low as $20. travelgrove |
 | $714* | Chicago | To Chicago $698 from Salt Lake City: flight + 2 nights hotel (SLC-ORD) bookingwiz.com |
 | $31* | Chicago | Bid for your own Mid-Size Car rentals provided by Priceline in Chicago, IL starting from $30. travelgrove |
 | $652* | Chicago | To Chicago $638 from Austin: flight + 2 nights hotel (AUS-ORD) bookingwiz.com |
 | $591* | Chicago | To Chicago $578 from Boston: flight + 2 nights hotel (BOS-ORD) bookingwiz.com |
 | $77* | Chicago | $75* - $75.00 & up 3.5-star hotels in Chicago bookingwiz.com |
 | $805* | Chicago | To Chicago $787 from Omaha: flight + 3 nights hotel (OMA-ORD) bookingwiz.com |
 | $832* | Chicago | To Chicago $814 from Washington DC: flight + 3 nights hotel (DCA-ORD) bookingwiz.com |
 | $648* | Chicago | To Chicago $634 from Buffalo: flight + 2 nights hotel (BUF-ORD) bookingwiz.com |
 | $755* | Chicago | To Chicago $738 from Orange County: flight + 2 nights hotel (SNA-ORD) bookingwiz.com |
 | $1002* | Chicago | To Chicago $980 from Oakland: flight + 2 nights hotel (OAK-ORD) bookingwiz.com |
 | $857* | Chicago | To Chicago $838 from Philadelphia: flight + 2 nights hotel (PHL-ORD) bookingwiz.com |
 | $591* | Chicago | To Chicago $578 from Fort Lauderdale: flight + 2 nights hotel (FLL-ORD) bookingwiz.com |
 | $1009* | Chicago | To Chicago $987 from Portland: flight + 2 nights hotel (PDX-ORD) bookingwiz.com |
 | $755* | Chicago | To Chicago $738 from San Francisco: flight + 2 nights hotel (SFO-ORD) bookingwiz.com |
 | $679* | Chicago | To Chicago $664 from Miami: flight + 2 nights hotel (MIA-ORD) bookingwiz.com |
 | $648* | Chicago | To Chicago $634 from New York: flight + 3 nights hotel (LGA-ORD) bookingwiz.com |
 | $131* | Lincolnshire | Homewood Suites By HiltonĀ® Chicago-lincolnshire, Lincolnshire ebookers.com |
 | $67* | Chicago | Best Premium Car rentals in Chicago, IL starting from as low as $65. travelgrove |
 | $46* | Chicago | Best Standard SUV rentals in Chicago, IL starting from as low as $45. travelgrove |
 | $693* | Chicago | To Chicago $678 from Phoenix: flight + 2 nights hotel (PHX-ORD) bookingwiz.com |
 | $656* | Chicago | To Chicago $642 from Tampa: flight + 2 nights hotel (TPA-ORD) bookingwiz.com |
 | $41* | Chicago | Bid for your own Premium Car rentals provided by Priceline in Chicago, IL starting from $40. travelgrove |
 | $62* | Chicago | Best MiniVan rentals in Chicago, IL starting from as low as $60. travelgrove |
 | $53* | Chicago | $51* - $51.00 & up 3-star hotels in Chicago bookingwiz.com |
 | $717* | Chicago | To Chicago $701 from Las Vegas: flight + 2 nights hotel (LAS-ORD) bookingwiz.com |
 | $36* | Chicago | Best Standard SUV rentals in Chicago, IL starting from as low as $35. travelgrove |
 | $866* | Chicago | To Chicago $847 from Washington DC: flight + 2 nights hotel (IAD-ORD) bookingwiz.com |
 | $62* | South Beloit | South Beloit Inn, South Beloit ebookers.com |
 | $670* | Chicago | To Chicago $655 from New York: flight + 3 nights hotel (JFK-ORD) bookingwiz.com |
 | $632* | Chicago | To Chicago $618 from Orlando: flight + 2 nights hotel (MCO-ORD) bookingwiz.com |
 | $761* | Chicago | To Chicago $744 from Dallas: flight + 2 nights hotel (DFW-ORD) bookingwiz.com |
 | $571* | Chicago | To Chicago $558 from Denver: flight + 2 nights hotel (DEN-ORD) bookingwiz.com |
 | $703* | Chicago | To Chicago $688 from Los Angeles: flight + 2 nights hotel (LAX-ORD) bookingwiz.com |
 | $530* | Chicago | To Chicago $518 from Indianapolis: flight + 2 nights hotel (IND-ORD) bookingwiz.com |
 | $35* | Chicago | Get the cheapest Economy Car rental in Chicago, IL, starting from as low as $34. travelgrove |
 | $727* | Chicago | To Chicago $711 from Providence: flight + 2 nights hotel (PVD-ORD) bookingwiz.com |
 | $849* | Chicago | To Chicago $830 from San Diego: flight + 3 nights hotel (SAN-ORD) bookingwiz.com |
 | $550* | Chicago | To Chicago $538 from St Louis: flight + 2 nights hotel (STL-ORD) bookingwiz.com |
 | $793* | Chicago | To Chicago $776 from Raleigh: flight + 2 nights hotel (RDU-ORD) bookingwiz.com |
 | $1012* | Chicago | To Chicago $990 from Sacramento: flight + 2 nights hotel (SMF-ORD) bookingwiz.com |
 | $530* | Chicago | To Chicago $518 from Cleveland: flight + 2 nights hotel (CLE-ORD) bookingwiz.com |
 | $94* | Carol Stream | Hampton Inn Chicago-carol Stream, Carol Stream ebookers.com |
 | $27* | Chicago | Bid for your own Mid-Size Car rentals provided by Priceline in Chicago, IL starting from $26. travelgrove |
 | $26* | Chicago | Get the cheapest Economy Car rental in Chicago, IL, starting from as low as $25. travelgrove |
 | $62* | Chicago | Bid for your own MiniVan rentals provided by Priceline in Chicago, IL starting from $60. travelgrove |
 | $189* | Chicago | $184: 4-star Chicago hotel + Save 30%, May 27 to May 28 bookingwiz.com |
 | $499* | Chicago | To Chicago $488 from Atlanta: flight + 2 nights hotel (ATL-ORD) bookingwiz.com |
 | $640* | Chicago | To Chicago $626 from Houston: flight + 2 nights hotel (IAH-ORD) bookingwiz.com |
 | $38* | Chicago | Best Mid-Size SUV rentals in Chicago, IL starting from as low as $37. travelgrove |
 | $764* | Chicago | To Chicago $747 from Baltimore: flight + 2 nights hotel (BWI-ORD) bookingwiz.com |
 | $654* | Chicago | To Chicago $640 from Newark: flight + 3 nights hotel (EWR-ORD) bookingwiz.com |
 | $926* | Chicago | To Chicago $906 from Hartford: flight + 2 nights hotel (BDL-ORD) bookingwiz.com |
 | $527* | Chicago | To Chicago $515 from Nashville: flight + 2 nights hotel (BNA-ORD) bookingwiz.com |
 | $848* | Chicago | To Chicago $829 from Milwaukee: flight + 2 nights hotel (MKE-ORD) bookingwiz.com |
 | SAVE | Chicago | From $49.00: 3-star hotels in Chicago bookingwiz.com |
 | $921* | Chicago | To Chicago $901 from Seattle: flight + 2 nights hotel (SEA-ORD) bookingwiz.com |
 | $530* | Chicago | To Chicago $518 from Columbus: flight + 2 nights hotel (CMH-ORD) bookingwiz.com |
 | $46* | Chicago | Bid for your own Full-Size Car rentals provided by Priceline in Chicago, IL starting from $45. travelgrove |